Enantioselective Cascade Reactions of Stable Sulfur Ylides and Nitroolefins through an Axial-to-Central Chirality Transfer Strategy
作者:
Lu, Liang-Qiu;Ming, Zhi-Hui;An, Jing;Li, Chao;Chen, Jia-Rong;...
期刊:
JOURNAL OF ORGANIC CHEMISTRY ,2012年77(2):1072-1080 ISSN:0022-3263
通讯作者:
Xiao, Wen-Jing
作者机构:
[Lu, Liang-Qiu; Ming, Zhi-Hui; Xiao, Wen-Jing; Chen, Jia-Rong; Li, Chao; An, Jing] Cent China Normal Univ, Coll Chem, Minist Educ, Key Lab Pesticide & Chem Biol, Wuhan 430079, Hubei, Peoples R China.;[Xiao, Wen-Jing] Cent China Normal Univ, Coll Chem, Minist Educ, Key Lab Pesticide & Chem Biol, 152 Luoyu Rd, Wuhan 430079, Hubei, Peoples R China.
通讯机构:
[Xiao, Wen-Jing] C;Cent China Normal Univ, Coll Chem, Minist Educ, Key Lab Pesticide & Chem Biol, 152 Luoyu Rd, Wuhan 430079, Hubei, Peoples R China.
摘要:
An enantioselective [4 + 1] annulation/rearrangement cascade of stable sulfur ylides and nitroolefins has been developed through an efficient axial-to-central chirality transfer with the use of a chiral BINOL-derived sulfide as a reliable stereocontroller. It can provide pharmaceutically and synthetically important oxazolidinones in high stereoselectivities (up to 96:4 e.r. and >95:5 d.r.). Moreover, this strategy was also successfully applied to the asymmetric [4 + 1]/[3 + 2] cycloaddition cascade of sulfur ylides with alkene-tethered nitroolefins, and the corresponding enantioenriched fused heterocycles (up to 87:13 e.r. and >95:5 d.r.) were obtained in good to excellent yields (54-95% yields). © 2011 American Chemical Society.
语种:
英文
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Synthesis of Indolo[1,2-a]Quinoxalines via a Pd-Catallyzed Regioselective C-H Olefination/Cyclization Sequence
作者:
Wang, Liang;Guo, Wei;Zhang, Xiao-Xiao;Xia, Xu-Dong;Xiao, Wen-Jing*
期刊:
Organic Letters ,2012年14(3):740-743 ISSN:1523-7060
通讯作者:
Xiao, Wen-Jing
作者机构:
[Xia, Xu-Dong; Guo, Wei; Xiao, Wen-Jing; Wang, Liang; Zhang, Xiao-Xiao] Cent China Normal Univ, Coll Chem, Minist Educ, Key Lab Pesticide & Chem Biol, Wuhan 430079, Hubei, Peoples R China.;[Xiao, Wen-Jing] Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Organometall Chem, Shanghai 200032, Peoples R China.;[Xiao, Wen-Jing] Cent China Normal Univ, Coll Chem, Minist Educ, Key Lab Pesticide & Chem Biol, 152 Luoyu Rd, Wuhan 430079, Hubei, Peoples R China.
通讯机构:
[Xiao, Wen-Jing] C;Cent China Normal Univ, Coll Chem, Minist Educ, Key Lab Pesticide & Chem Biol, 152 Luoyu Rd, Wuhan 430079, Hubei, Peoples R China.
摘要:
A highly efficient approach to indolo [1,2-a]quinoxaline derivatives through a Pd-catalyzed regioselective C-H olefination/cyclization sequence has been developed. This transformation has a wide range of substrates with various functional groups, and the corresponding heterocyclic products were obtained in good yields.
语种:
英文
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Development of Cascade Reactions for Rapid Construction of Diverse Heterocyclic Architectures
作者:
Wen-Jing Xiao;Jia-Rong Chen;Liang-Qiu Lu;Xu-Fan Wang
作者机构:
[Wen-Jing Xiao; Jia-Rong Chen; Liang-Qiu Lu; Xu-Fan Wang] Key Laboratory of Pesticide & Chemical Biology, Ministry of Education, College of Chemistry, Central China Normal University, 152 Luoyu Road, Wuhan, Hubei 430079
会议名称:
中国化学会第七届有机化学学术会议
会议时间:
2011-11-12
会议地点:
南京
会议主办单位:
中国化学会;国际自然科学基金委员会
会议论文集名称:
中国化学会第七届有机化学学术会议论文集
关键词:
sulfur ylide;cascade reaction;nitroolefin
语种:
英文
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Catalytic Asymmetric Aza-Michael-Michael Addition Cascade: Enantioselective Synthesis of Polysubstituted 4-Aminobenzopyrans
作者:
Wang, Xu-Fan;An, Jing;Zhang, Xiao-Xiao;Tan, Fen;Chen, Jia-Rong* ;...
期刊:
Organic Letters ,2011年13(4):808-811 ISSN:1523-7060
通讯作者:
Chen, Jia-Rong
作者机构:
[Wang, Xu-Fan; Tan, Fen; Xiao, Wen-Jing; Chen, Jia-Rong; An, Jing; Zhang, Xiao-Xiao] Cent China Normal Univ, Minist Educ, Coll Chem, Key Lab Pesticide & Chem Biol, Wuhan 430079, Hubei, Peoples R China.
通讯机构:
[Chen, Jia-Rong] C;Cent China Normal Univ, Minist Educ, Coll Chem, Key Lab Pesticide & Chem Biol, Wuhan 430079, Hubei, Peoples R China.
摘要:
A catalytic asymmetric aza-Michael-Michael addition cascade of anilines to nitroolefin enoates in the presence of chiral bifunctional thiourea catalysts has been disclosed. This reaction provides a mild and efficient approach to polysubstituted chiral 4-aminobenzopyrans bearing three consecutive stereocenters in high yields with excellent stereoselectivities.
语种:
英文
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Organocatalytic multiple cascade reactions: A new strategy for the construction of enantioenriched tetrahydrocarbazoles
作者:
Cao, Yi-Ju;Cheng, Hong-Gang;Lu, Liang-Qiu;Zhang, Ji-Ji;Cheng, Ying;...
期刊:
ADVANCED SYNTHESIS & CATALYSIS ,2011年353(4):617-623 ISSN:1615-4150
通讯作者:
Chen, Jia-Rong
作者机构:
[Cheng, Hong-Gang; Lu, Liang-Qiu; Cheng, Ying; Xiao, Wen-Jing; Chen, Jia-Rong; Zhang, Ji-Ji; Cao, Yi-Ju] Cent China Normal Univ, Coll Chem, Minist Educ, Key Lab Pesticide & Chem Biol, Wuhan 430079, Hubei, Peoples R China.;[Chen, Jia-Rong] Cent China Normal Univ, Coll Chem, Minist Educ, Key Lab Pesticide & Chem Biol, 152 Luoyu Rd, Wuhan 430079, Hubei, Peoples R China.
通讯机构:
[Chen, Jia-Rong] C;Cent China Normal Univ, Coll Chem, Minist Educ, Key Lab Pesticide & Chem Biol, 152 Luoyu Rd, Wuhan 430079, Hubei, Peoples R China.
关键词:
cascade reactions;enantioselectivity;organocatalysis;tetrahydrocarbazoles
摘要:
A novel cascade Friedel-Crafts alkylation/Michael addition/aromatization reaction of 2-vinylindoles with α,β-unsaturated aldehydes has been developed for the construction of functionalized tetrahydrocarbazoles. The products were obtained in up to 97% yield and with excellent stereoselectivities (ee up to > 99%, dr up to > 99:1). © 2011 Wiley-VCH Verlag GmbH & Co. KGaA.
语种:
英文
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Visible light-induced intramolecular cyclization reactions of diamines: a new strategy to construct tetrahydroimidazoles
作者:
Xuan, Jun;Cheng, Ying;An, Jing;Lu, Liang-Qiu;Zhang, Xiao-Xiao;...
期刊:
Chemical Communications ,2011年47(29):8337-8339 ISSN:1359-7345
通讯作者:
Xiao, Wen-Jing
作者机构:
[Lu, Liang-Qiu; Cheng, Ying; Xiao, Wen-Jing; Xuan, Jun; An, Jing; Zhang, Xiao-Xiao] Cent China Normal Univ, Key Lab Pesticide & Chem Biol, Minist Educ, Coll Chem, Wuhan 430079, Hubei, Peoples R China.;[Xiao, Wen-Jing] Cent China Normal Univ, Key Lab Pesticide & Chem Biol, Minist Educ, Coll Chem, 152 Luoyu Rd, Wuhan 430079, Hubei, Peoples R China.
通讯机构:
[Xiao, Wen-Jing] C;Cent China Normal Univ, Key Lab Pesticide & Chem Biol, Minist Educ, Coll Chem, 152 Luoyu Rd, Wuhan 430079, Hubei, Peoples R China.
摘要:
A new and efficient synthesis of highly substituted tetrahydroimidazole derivatives by means of visible light-induced intramolecular cyclization reactions has been described. This photoredox catalytic reaction exhibited high diastereoselectivity and afforded the desired products in good yields.
语种:
英文
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Facile Synthesis of Enantioenriched C-gamma-Tetrasubstituted alpha-Amino Acid Derivatives via an Asymmetric Nucleophilic Addition/Protonation Cascade
作者:
Duan, Shu-Wen;An, Jing;Chen, Jia-Rong* ;Xiao, Wen-Jing
期刊:
Organic Letters ,2011年13(9):2290-2293 ISSN:1523-7060
通讯作者:
Chen, Jia-Rong
作者机构:
[Duan, Shu-Wen; Xiao, Wen-Jing; Chen, Jia-Rong; An, Jing] Cent China Normal Univ, Key Lab Pesticide & Chem Biol, Minist Educ, Coll Chem, Wuhan 430079, Hubei, Peoples R China.;[Chen, Jia-Rong] Cent China Normal Univ, Key Lab Pesticide & Chem Biol, Minist Educ, Coll Chem, 152 Luoyu Rd, Wuhan 430079, Hubei, Peoples R China.
通讯机构:
[Chen, Jia-Rong] C;Cent China Normal Univ, Key Lab Pesticide & Chem Biol, Minist Educ, Coll Chem, 152 Luoyu Rd, Wuhan 430079, Hubei, Peoples R China.
摘要:
Chemical equations presented. An asymmetric nucleophilic addition/protonation reaction of 3-substituted oxindoles and ethyl 2-phthalimidoacrylate has been described. This strategy can give direct access to Cγ-tetrasubstituted α-amino acid derivatives bearing 1,3-nonadjacent stereocenters with up to 98% yield, 94:6 dr, and >99% ee. Dual activation is proposed in the transition state, and the opposite enantiomers can be obtained simply by changing cinchonidine-derived catalyst to the cinchonine analogue. © 2011 American Chemical Society.
语种:
英文
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Brønsted acid catalyzed Diels–Alder reactions of 2-vinylindoles and 3-nitrocoumarins: an expedient synthesis of coumarin-fused tetrahydrocarbazoles
作者:
Tan, Fen;Li, Fang;Zhang, Xiao-Xiao;Wang, Xu-Fan;Cheng, Hong-Gang;...
期刊:
Tetrahedron ,2011年67(2):446-451 ISSN:0040-4020
通讯作者:
Chen, Jia-Rong
作者机构:
[Wang, Xu-Fan; Cheng, Hong-Gang; Li, Fang; Tan, Fen; Xiao, Wen-Jing; Chen, Jia-Rong; Zhang, Xiao-Xiao] Cent China Normal Univ, Coll Chem, Minist Educ, Key Lab Pesticide & Chem Biol, Wuhan 430079, Hubei, Peoples R China.;[Chen, Jia-Rong] Cent China Normal Univ, Coll Chem, Minist Educ, Key Lab Pesticide & Chem Biol, 152 Luoyu Rd, Wuhan 430079, Hubei, Peoples R China.
通讯机构:
[Chen, Jia-Rong] C;Cent China Normal Univ, Coll Chem, Minist Educ, Key Lab Pesticide & Chem Biol, 152 Luoyu Rd, Wuhan 430079, Hubei, Peoples R China.
关键词:
Organocatalysis;Diels-Alder reaction;Coumarin;Tetrahydrocarbazole
摘要:
A Brønsted acid catalyzed Diels–Alder reaction of 2-vinylindoles and 3-nitrocoumarins has been described. The methodology allows a rapid and expedient synthesis of a variety of coumarin-fused polycyclic indoles in good yields (up to 82%) with high diastereoselectivities (up to >19:1).
语种:
英文
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Organocatalytic Conjugate Additions of Acetylacetone to 3-Ylideneoxindoles: A Direct Access to Highly Enantioenriched Oxindole Derivatives
作者:
Duan, Shu-Wen;Lu, Hai-Hua;Zhang, Fu-Gen;Xuan, Jun;Chen, Jia-Rong;...
期刊:
SYNTHESIS-STUTTGART ,2011年2011(12):1847-1852 ISSN:0039-7881
通讯作者:
Xiao, Wen-Jing
作者机构:
[Duan, Shu-Wen; Xiao, Wen-Jing; Lu, Hai-Hua; Chen, Jia-Rong; Xuan, Jun; Zhang, Fu-Gen] Cent China Normal Univ, Coll Chem, Minist Educ, Key Lab Pesticide & Chem Biol, Wuhan 430079, Hubei, Peoples R China.;[Xiao, Wen-Jing] Cent China Normal Univ, Coll Chem, Minist Educ, Key Lab Pesticide & Chem Biol, 152 Luoyu Rd, Wuhan 430079, Hubei, Peoples R China.
通讯机构:
[Xiao, Wen-Jing] C;Cent China Normal Univ, Coll Chem, Minist Educ, Key Lab Pesticide & Chem Biol, 152 Luoyu Rd, Wuhan 430079, Hubei, Peoples R China.
关键词:
organocatalysis;bifunctional activation;oxindole;conjugate addition;3-ylideneoxindole
摘要:
A highly enantioselective organocatalytic conjugate addition of acetylacetone to 3-ylideneoxindoles is described. This method provides polysubstituted oxindoles in good to excellent enantioselectivities and high isolated yields. ©Georg Thieme Verlag Stuttgart - New York.
语种:
英文
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Palladium-catalyzed C-H acetoxylation of 2-methoxyimino-2-aryl-acetates and acetamides
作者:
Wang, Liang;Xia, Xu-Dong;Guo, Wei;Chen, Jia-Rong;Xiao, Wen-Jing*
期刊:
Organic & Biomolecular Chemistry ,2011年9(20):6895-6898 ISSN:1477-0520
通讯作者:
Xiao, Wen-Jing
作者机构:
[Xia, Xu-Dong; Guo, Wei; Xiao, Wen-Jing; Chen, Jia-Rong; Wang, Liang] Cent China Normal Univ, Coll Chem, Minist Educ, Key Lab Pesticide & Chem Biol, Wuhan 430079, Hubei, Peoples R China.;[Xiao, Wen-Jing] Cent China Normal Univ, Coll Chem, Minist Educ, Key Lab Pesticide & Chem Biol, 152 Luoyu Rd, Wuhan 430079, Hubei, Peoples R China.
通讯机构:
[Xiao, Wen-Jing] C;Cent China Normal Univ, Coll Chem, Minist Educ, Key Lab Pesticide & Chem Biol, 152 Luoyu Rd, Wuhan 430079, Hubei, Peoples R China.
摘要:
Palladium-catalyzed C-H acetoxylation reactions of 2-methoxyimino-2-aryl- acetates and acetamides have been developed. These transformations feature excellent regioselectivity, wide substrate scope, and moderate to good yields. The product can be easily converted into naturally unprecedented α-amino acids in excellent yields. ©2011 The Royal Society of Chemistry.
语种:
英文
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Asymmetric Cyclopropanation of beta,gamma-Unsaturated alpha-Ketoesters with Stabilized Sulfur Ylides Catalyzed by C-2-Symmetric Ureas
作者:
Cheng, Ying;An, Jing;Lu, Liang-Qiu;Luo, Lan;Wang, Zheng-Yi;...
期刊:
JOURNAL OF ORGANIC CHEMISTRY ,2011年76(1):281-284 ISSN:0022-3263
通讯作者:
Chen, Jia-Rong
作者机构:
[Wang, Zheng-Yi; Lu, Liang-Qiu; Cheng, Ying; Luo, Lan; Xiao, Wen-Jing; Chen, Jia-Rong; An, Jing] Cent China Normal Univ, Coll Chem, Minist Educ, Key Lab Pesticide & Chem Biol, Wuhan 430079, Hubei, Peoples R China.;[Chen, Jia-Rong] Cent China Normal Univ, Coll Chem, Minist Educ, Key Lab Pesticide & Chem Biol, 152 Luoyu Rd, Wuhan 430079, Hubei, Peoples R China.
通讯机构:
[Chen, Jia-Rong] C;Cent China Normal Univ, Coll Chem, Minist Educ, Key Lab Pesticide & Chem Biol, 152 Luoyu Rd, Wuhan 430079, Hubei, Peoples R China.
摘要:
A novel organocatalytic asymmetric cyclopropanation of β,γ- unsaturated α-ketoesters with stabilized sulfur ylides using C <inf>2</inf>-symmetric urea as a hydrogen-bond catalyst has been described. This reaction allows an efficient access to 1,2,3-trisubstituted cyclopropane derivatives in moderate to good yields with up to 16:1 dr and 90:10 er under mild reaction conditions. The mechanism study proved that the high stereoinduction originated from the cooperative effect of the hydrogen-bond catalyst. ©2010 American Chemical Society.
语种:
英文
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Pyrrolidinyl-sulfamide derivatives as a new class of bifunctional organocatalysts for direct asymmetric Michael addition of cyclohexanone to nitroalkenes
作者:
Chen, Jia-Rong* ;Fu, Liang;Zou, You-Quan;Chang, Ning-Jie;Rong, Jian;...
期刊:
Organic & Biomolecular Chemistry ,2011年9(14):5280-5287 ISSN:1477-0520
通讯作者:
Chen, Jia-Rong
作者机构:
[Chang, Ning-Jie; Rong, Jian; Fu, Liang; Xiao, Wen-Jing; Chen, Jia-Rong; Zou, You-Quan] Cent China Normal Univ, Key Lab Pesticide & Chem Biol, Minist Educ, Coll Chem, Wuhan 430079, Hubei, Peoples R China.;[Chen, Jia-Rong] Cent China Normal Univ, Key Lab Pesticide & Chem Biol, Minist Educ, Coll Chem, 152 Luoyu Rd, Wuhan 430079, Hubei, Peoples R China.
通讯机构:
[Chen, Jia-Rong] C;Cent China Normal Univ, Key Lab Pesticide & Chem Biol, Minist Educ, Coll Chem, 152 Luoyu Rd, Wuhan 430079, Hubei, Peoples R China.
摘要:
A series of chiral pyrrolidinyl-sulfamide derivatives have been identified as efficient bifunctional organocatalysts for the direct Michael addition of cyclohexanone to a wide range of nitroalkenes. The desired Michael adducts were obtained in high chemical yields and excellent stereoselectivities (up to 99/1 dr and 95% ee).
语种:
英文
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Enantioselective synthesis of chromans with a quaternary stereogenic centre through catalytic asymmetric cascade reactions
作者:
Hua, Qiu-Lin;Li, Chao;Wang, Xu-Fan;Lu, Liang-Qiu;Chen, Jia-Rong* ;...
期刊:
ACS CATALYSIS ,2011年1(3):221-226 ISSN:2155-5435
通讯作者:
Chen, Jia-Rong
作者机构:
[Wang, Xu-Fan; Lu, Liang-Qiu; Xiao, Wen-Jing; Chen, Jia-Rong; Li, Chao; Hua, Qiu-Lin] Cent China Normal Univ, Coll Chem, Minist Educ, Key Lab Pesticide & Chem Biol, Wuhan 430079, Hubei, Peoples R China.;[Chen, Jia-Rong] Cent China Normal Univ, Coll Chem, Minist Educ, Key Lab Pesticide & Chem Biol, 152 Luoyu Rd, Wuhan 430079, Hubei, Peoples R China.
通讯机构:
[Chen, Jia-Rong] C;Cent China Normal Univ, Coll Chem, Minist Educ, Key Lab Pesticide & Chem Biol, 152 Luoyu Rd, Wuhan 430079, Hubei, Peoples R China.
关键词:
organocatalysis;cascade reaction;Michael addition;heterocycle;chromans
摘要:
A highly enantioselective cascade reaction of benzotriazoles with nitroolefin-containing enonates catalyzed by a base/acid bifunctional organocatalyst has been developed. This cascade sequence affords efficient access to densely functionalized chiral chromans with a quaternary stereogenic center in high yield (up to 91%) with excellent enantioselectivity (up to 96% ee) and diastereoselectivity (up to 96:4 dr). The reaction itself features simple experimental procedures under benign conditions and is completely atom-economic in character. © 2011 American Chemical Society.
语种:
英文
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Enantioselective organocatalytic Friedel-Crafts Alkylations
作者:
Lu, Hai-Hua;Tan, Fen;Xiao, Wen-Jing*
期刊:
CURRENT ORGANIC CHEMISTRY ,2011年15(24):4022-4045 ISSN:1385-2728
通讯作者:
Xiao, Wen-Jing
作者机构:
[Tan, Fen; Xiao, Wen-Jing; Lu, Hai-Hua] Cent China Normal Univ, Key Lab Pesticide & Chem Biol, Coll Chem, Minist Educ, Wuhan 430079, Hubei, Peoples R China.;[Xiao, Wen-Jing] Cent China Normal Univ, Key Lab Pesticide & Chem Biol, Coll Chem, Minist Educ, 152 Luoyu Rd, Wuhan 430079, Hubei, Peoples R China.
通讯机构:
[Xiao, Wen-Jing] C;Cent China Normal Univ, Key Lab Pesticide & Chem Biol, Coll Chem, Minist Educ, 152 Luoyu Rd, Wuhan 430079, Hubei, Peoples R China.
关键词:
Organocatalysis;Friedel-Crafts alkylation;iminium catalysis;SOMO catalysis;hydrogen-bonding catalysis;Enantioselective;chiral amine catalysts;organometallic/bioorganic methods;carbon-carbon;carbon-heteroatom;α β-unsaturated aldehydes;organic synthesis;Alkylation with Enals;covalent;alkylation chemistry
摘要:
Over the last few decades, the catalytic asymmetric Friedel-Crafts alkylation has become a powerful strategy that provides enantioenriched structural motifs of established value in medicinal chemistry or complex target synthesis. While the traditionally chiral Lewis-acid catalyzed Friedel-Crafts alkylation has been extensively reviewed in the literature, we focused this review on the recent advances on organocatalytic Friedel-Crafts alkylations. According to activation modes, this review is divided into three main sections, including 1) alkylations via iminium catalysis, 2) alkylations via SOMO catalysis, and 3) alkylations by chiral hydrogen-bond donors.
语种:
英文
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Efficient and general synthesis of oxazino[4,3-a]indoles by cascade addition-cyclization reactions of (1H-indol-2-yl)methanols and vinyl sulfonium salts
作者:
An, Jing;Chang, Ning-Jie;Song, Li-Dong;Jin, Yu-Qin;Ma, Ying;...
期刊:
Chemical Communications ,2011年47(6):1869-1871 ISSN:1359-7345
通讯作者:
Chen, Jia-Rong
作者机构:
[Chang, Ning-Jie; Song, Li-Dong; Xiao, Wen-Jing; Ma, Ying; Chen, Jia-Rong; Jin, Yu-Qin; An, Jing] Cent China Normal Univ, Coll Chem, Minist Educ, Key Lab Pesticide & Chem Biol, Wuhan 430079, Hubei, Peoples R China.;[Chen, Jia-Rong] Cent China Normal Univ, Coll Chem, Minist Educ, Key Lab Pesticide & Chem Biol, 152 Luoyu Rd, Wuhan 430079, Hubei, Peoples R China.
通讯机构:
[Chen, Jia-Rong] C;Cent China Normal Univ, Coll Chem, Minist Educ, Key Lab Pesticide & Chem Biol, 152 Luoyu Rd, Wuhan 430079, Hubei, Peoples R China.
摘要:
An efficient and general approach to oxazino[4,3-a]indole architectures is described. The addition-cyclization cascade of (1H-indol-2-yl)methanols with vinyl sulfonium salts affords oxazino[4,3-a]indole derivatives in high yields.
语种:
英文
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A Practical and Enantioselective Approach to Tetrahydrocarbazoles by Asymmetric Organocatalysis
作者:
Zhu, Xiao-Yu;An, Xiao-Lei;Li, Chang-Feng;Zhang, Fu-Gen;Hua, Qiu-Lin;...
期刊:
ChemCatChem ,2011年3(4):679-683 ISSN:1867-3880
通讯作者:
Chen, Jia-Rong
作者机构:
[Xiao, Wen-Jing; Chen, Jia-Rong; An, Xiao-Lei; Li, Chang-Feng; Zhang, Fu-Gen; Hua, Qiu-Lin; Zhu, Xiao-Yu] Cent China Normal Univ, Coll Chem, Minist Educ, Key Lab Pesticide & Chem Biol, Wuhan 430079, Hubei, Peoples R China.;[Chen, Jia-Rong] Cent China Normal Univ, Coll Chem, Minist Educ, Key Lab Pesticide & Chem Biol, 152 Luoyu Rd, Wuhan 430079, Hubei, Peoples R China.
通讯机构:
[Chen, Jia-Rong] C;Cent China Normal Univ, Coll Chem, Minist Educ, Key Lab Pesticide & Chem Biol, 152 Luoyu Rd, Wuhan 430079, Hubei, Peoples R China.
关键词:
alkylation;asymmetric synthesis;enantioselectivity;heterocycles;organocatalysis
摘要:
The intramolecular Friedel—Crafts-type alkylation of ω-indolyl α,β-unsaturated aldehydes in the presence of chiral amines affords the title carbazole derivatives with up to 98% enantioselectivity.
语种:
英文
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Visible-light-induced oxidation/[3+2] cycloaddition/oxidative aromatization sequence: A photocatalytic strategy to construct pyrrolo[2,1-a]isoquinolines
作者:
Zou, You-Quan;Lu, Liang-Qiu;Fu, Liang;Chang, Ning-Jie;Rong, Jian;...
期刊:
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION ,2011年50(31):7171-7175 ISSN:1433-7851
通讯作者:
Xiao, Wen-Jing
作者机构:
[Lu, Liang-Qiu; Chang, Ning-Jie; Rong, Jian; Fu, Liang; Xiao, Wen-Jing; Chen, Jia-Rong; Zou, You-Quan] Cent China Normal Univ, Minist Educ, Coll Chem, Key Lab Pesticide & Chem Biol, Wuhan 430079, Hubei, Peoples R China.;[Xiao, Wen-Jing] Cent China Normal Univ, Minist Educ, Coll Chem, Key Lab Pesticide & Chem Biol, 152 Luoyu Rd, Wuhan 430079, Hubei, Peoples R China.
通讯机构:
[Xiao, Wen-Jing] C;Cent China Normal Univ, Minist Educ, Coll Chem, Key Lab Pesticide & Chem Biol, 152 Luoyu Rd, Wuhan 430079, Hubei, Peoples R China.
关键词:
alkaloids;oxygen;photochemistry;tandem reactions;visible light
摘要:
A ray of sunshine: The title reaction sequence using ethyl 2-(3,4-dihydroisoquinolin-2(1H)-yl)acetates with a series of electron-deficient alkenes and alkynes provides rapid and efficient access to pyrrolo[2,1-a] isoquinolines (see scheme; bpy=2,2′-bipyridine, EWG=electron-withdrawing group). The reaction offers a strategically new protocol for the direct and efficient construction of the core structure of naturally occurring lamellarin alkaloids. Copyright © 2011 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
语种:
英文
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Phosphine-Catalyzed [3+2] Cycloadditions of 2-Phenyl-4-Arylidene-5(4H)-Oxazolones with Allenoate: A Concise Synthesis of Aspartic Acid Analogues
作者:
Zou, You-Quan;Li, Chao;Rong, Jian;Yan, Hao;Chen, Jia-Rong* ;...
期刊:
SYNLETT ,2011年2011(7):1000-1004 ISSN:0936-5214
通讯作者:
Chen, Jia-Rong
作者机构:
[Rong, Jian; Xiao, Wen-Jing; Chen, Jia-Rong; Yan, Hao; Li, Chao; Zou, You-Quan] Cent China Normal Univ, Key Lab Pesticide & Chem Biol, Minist Educ, Coll Chem, Wuhan 430079, Hubei, Peoples R China.;[Chen, Jia-Rong] Cent China Normal Univ, Key Lab Pesticide & Chem Biol, Minist Educ, Coll Chem, 152 Luoyu Rd, Wuhan 430079, Hubei, Peoples R China.
通讯机构:
[Chen, Jia-Rong] C;Cent China Normal Univ, Key Lab Pesticide & Chem Biol, Minist Educ, Coll Chem, 152 Luoyu Rd, Wuhan 430079, Hubei, Peoples R China.
关键词:
cycloaddition;organocatalysis;phosphine;benzyl 2,3-butadienoate;aspartic acid analogues
摘要:
A Ph3P-catalyzed [3+2] cycloaddition of 2-phenyl-4-arylidene- 5(4H)-oxazolones with benzyl 2,3-butadienoate has been developed for the efficient synthesis of structurally diverse and conformationally constrained aspartic acid analogues. © Georg Thieme Verlag Stuttgart · New York.
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英文
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Erratum: Enantioselective synthesis of chromans with a quaternary stereogenic centre through catalytic asymmetric cascade reactions (ACS Catalysis (2011) 1 (221-226) DOI: 10.0121/cs100161k)
作者:
Hua, Qiu-Lin;Li, Chao;Wang, Xu-Fan;Lu, Liang-Qiu;Chen, Jia-Rong* ;...
期刊:
ACS CATALYSIS ,2011年1(5):573 ISSN:2155-5435
通讯作者:
Chen, Jia-Rong
作者机构:
[Wang, Xu-Fan; Lu, Liang-Qiu; Xiao, Wen-Jing; Chen, Jia-Rong; Li, Chao; Hua, Qiu-Lin] Cent China Normal Univ, Coll Chem, Minist Educ, Key Lab Pesticide & Chem Biol, Wuhan 430079, Hubei, Peoples R China.;[Chen, Jia-Rong] Cent China Normal Univ, Coll Chem, Minist Educ, Key Lab Pesticide & Chem Biol, 152 Luoyu Rd, Wuhan 430079, Hubei, Peoples R China.
通讯机构:
[Chen, Jia-Rong] C;Cent China Normal Univ, Coll Chem, Minist Educ, Key Lab Pesticide & Chem Biol, 152 Luoyu Rd, Wuhan 430079, Hubei, Peoples R China.
语种:
英文
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Enantioselective intramolecular crossed rauhut-currier reactions through cooperative nucleophilic activation and hydrogen-bonding catalysis: Scope and mechanistic insight
作者:
Wang, Xu-Fan;Peng, Liang;An, Jing;Li, Chao;Yang, Qing-Qing;...
期刊:
CHEMISTRY-A EUROPEAN JOURNAL ,2011年17(23):6484-6491 ISSN:0947-6539
通讯作者:
Gu, Feng-Long
作者机构:
[Wang, Xu-Fan; Yang, Qing-Qing; Lu, Liang-Qiu; Xiao, Wen-Jing; Li, Chao; An, Jing] Cent China Normal Univ, Coll Chem, Minist Educ, Key Lab Pesticide & Chem Biol, Wuhan 430079, Hubei, Peoples R China.;[Peng, Liang; Gu, Feng-Long] S China Normal Univ, Ctr Computat Quantum Chem, Guangzhou 510009, Guangdong, Peoples R China.;[Gu, Feng-Long] S China Normal Univ, Ctr Computat Quantum Chem, W 55 Zhongshan Rd, Guangzhou 510009, Guangdong, Peoples R China.
通讯机构:
[Gu, Feng-Long] S;S China Normal Univ, Ctr Computat Quantum Chem, W 55 Zhongshan Rd, Guangzhou 510009, Guangdong, Peoples R China.
关键词:
asymmetric catalysis;cascade reactions;hydrogen bonds;Michael addition;Rauhut-Currier reaction
摘要:
A highly efficient and enantioselective intramolecular crossed Rauhut-Currier (RC) reaction of nitroolefins with tethered enonates has been developed through cooperative nucleophilic activation and a hydrogen-bonding catalytic strategy (≤98% ee and 98% yield). The reaction features simple experimental procedures and is completely chemoselective and atom-economic in character. The potential synthetic applications have been demonstrated by the conversion of the RC reaction products into biologically and pharmaceutically valuable compounds with highly diastereoselectivity. In addition, computational investigations were employed to support the proposed mechanism and to obtain a good understanding of the origin of the stereoselectivity in RC reactions. Copyright © 2011 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
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英文
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