作者机构:
[刘以银; 余晓叶; 陈加荣; 杨梦楠; 肖文精] College of Chemistry, Central China Normal University;[刘以银; 余晓叶; 陈加荣; 杨梦楠; 肖文精] 华师-渥太华大学国际联合研究中心,华中师范大学化学学院;[刘以银; 余晓叶; 陈加荣; 杨梦楠; 肖文精] 农药与化学生物学教育部重点实验室,华中师范大学化学学院
期刊:
Current Catalysis,2017年6(3):155-167 ISSN:2211-5447
作者机构:
CCNU-uOttawa Joint Research Centre, Hubei International Scientific and Technological Cooperation Base of Pesticide and Green Synthesis, Key Laboratory of Pesticide & Chemical Biology, Ministry of Education, College of Chemistry, Central China Normal University, 152 Luoyu Road, Wuhan, Hubei, 430079,China;[Yu, Xiao-Ye; Zhou, Fan; Xiao, Wen-Jing; Chen, Jia-Rong] CCNU-uOttawa Joint Research Centre, Hubei International Scientific and Technological Cooperation Base of Pesticide and Green Synthesis, Key Laboratory of Pesticide & Chemical Biology, Ministry of Education, College of Chemistry, Central China Normal University, 152 Luoyu Road, Wuhan, Hubei, 430079,China
摘要:
Background: Azlactones, also known as oxazolones, are a class of versatile intermediates and are commonly used for the synthesis of various heterocyclic scaffolds and unnatural α-amino acids. In particular, because of their inherent multiple sites of reactivity, azlactones have recently attracted a great deal of research efforts from the synthetic community. By exploring different sites of reactivity, a variety of cycloaddition reactions have been developed to construct diverse synthetically and biologically important hetereocycles as well as α-amino acid derivatives bearing quaternary carbons. With the development of asymmetric catalysis, a range of catalytic asymmetric variants have also been developed by metal and organocatalysis to access various valuable enantioenriched molecules. However, to the best of our knowledge, there is still no comprehensive review devoted to this emerging topic to date. Methods: We performed a systemic survey of azlactone-mediated cycloaddition reactions by SciFinder search. To calibrate the reasonable scope of this survey, we highlight the recent advances in the field of cycloaddition reactions of azlactones, and their applications to the construction of heterocycles according to the different types of reaction modes. Thus, thirty four leading papers were included in this review and accordingly organized by different sites of reactivity, including [2+3], [2+4], [2+8], and [3+2] cycloaddition reactions. Conclusion: The results shown in this review confirmed the significance of such type of versatile intermediates. The discovery of new suitable reactive species and application of other catalytic modes can provide a fruitful platform for the development of new cycloadditions of azlactones.
作者机构:
[Zhao, Yu; Xiao, Wen-Jing; Chen, Jia-Rong] Cent China Normal Univ, Key Lab Pesticides & Chem Biol, Hubei Int Sci & Technol Cooperat Base Pesticide &, Minist Educ,Coll Chem, 152 Luoyu Rd, Wuhan 430079, Hubei, Peoples R China.;[Xiao, Wen-Jing] Lanzhou Univ, State Key Lab Appl Organ Chem, Lanzhou 730000, Gansu, Peoples R China.
通讯机构:
[Xiao, Wen-Jing] C;[Xiao, Wen-Jing] L;Cent China Normal Univ, Key Lab Pesticides & Chem Biol, Hubei Int Sci & Technol Cooperat Base Pesticide &, Minist Educ,Coll Chem, 152 Luoyu Rd, Wuhan 430079, Hubei, Peoples R China.;Lanzhou Univ, State Key Lab Appl Organ Chem, Lanzhou 730000, Gansu, Peoples R China.
摘要:
A visible-light photocatalytic decarboxylative alkyl radical addition cascade reaction of acrylamide-tethered styrenes for the synthesis of benzazepine derivatives is described. This protocol features broad substrate scope, excellent functional group tolerance, and mild reaction conditions, affording the seven-membered rings in good yields. This method was also applied for efficient grafting of the benzazepine scaffold into the pharmaceutically active ursolic acid scaffold.
通讯机构:
[Lu, Liang-Qiu] C;Cent China Normal Univ, Coll Chem, Minist Educ,Key Lab Pesticide & Chem Biol, Hubei Int Sci & Technol Cooperat Base Pesticide &, 152 Luoyu Rd, Wuhan 430079, Hubei, Peoples R China.
摘要:
The palladium-catalyzed branch- and enantioselective allylic amination of vinyl benzoxazinones was accomplished through controlling the hydrogen bond direction. This protocol provides a rapid and efficient route for synthesizing an important building block, chiral amino alkene, from widely available aliphatic amines in 64 → 99% yields with up to 99% ee. Furthermore, this transformation and the accompanying products were utilized to develop one-pot reactions through dual catalysis, affording chiral indolines with good synthetic efficiency and excellent enantiocontrol.
作者机构:
[Lu Liangqiu] Cent China Normal Univ, Key Lab Pesticide & Chem Biol, Minist Educ, Wuhan 430079, Peoples R China.;Cent China Normal Univ, Coll Chem, Wuhan 430079, Peoples R China.
通讯机构:
[Lu Liangqiu] C;Cent China Normal Univ, Key Lab Pesticide & Chem Biol, Minist Educ, Wuhan 430079, Peoples R China.
作者机构:
[Chen, Dong-Zhen; Xiao, Wen-Jing; 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.;[Xiao, Wen-Jing] Shanghai Inst Organ Chem, State Key Lab Organometall Chem, 345 Lingling Rd, Shanghai 200032, 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 formal [4 + 1] annulation reaction of 3-bromooxindoles and in situ-derived 1,2-diaza-1,3-dienes in the presence of Cs2CO3 as the base has been developed for the first time. This protocol provides an efficient and mild approach for the synthesis of various biologically interesting spiropyrazoline oxindoles in generally high yields. A one-pot, three-component variant also worked smoothly to give the desired products in comparable yields.
通讯机构:
[Shi, De-Qing] 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 1,3-dipolar cycloaddition of 3-ylideneoxindoles with in-situ-generated α-diazoketones to potentially biological active spiro[pyrazolin-3,3′-oxindoles] 4 with excellent regioselectivity and diastereoselectivity and synthetically useful building block 3-arylcarbonylmethyl substituted ylideneoxindoles 5 in different conditions has been developed. This method has advantages of mild conditions, simple workup, and wide substrate scopes as well as without using any transition metal catalyst.
作者机构:
[Chen Jiarong] Cent China Normal Univ, Key Lab Pesticide & Chem Biol, Minist Educ, Wuhan 430079, Peoples R China.;Cent China Normal Univ, Coll Chem, Wuhan 430079, Peoples R China.
通讯机构:
[Chen Jiarong] C;Cent China Normal Univ, Key Lab Pesticide & Chem Biol, Minist Educ, Wuhan 430079, Peoples R China.
期刊:
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY,2017年139(1):63-66 ISSN:0002-7863
通讯作者:
Xiao, Wen-Jing
作者机构:
[Lu, Liang-Qiu; Xiao, Wen-Jing; Chen, Jia-Rong; Ding, Wei; Quan-Quan Zhou; Wei, Yi] Cent China Normal Univ, CCNU uOttawa Joint Res Ctr, Key Lab Pesticide & Chem Biol, Minist Educ,Coll Chem, 152 Luoyu Rd, Wuhan 430079, Peoples R China.
通讯机构:
[Xiao, Wen-Jing] C;Cent China Normal Univ, CCNU uOttawa Joint Res Ctr, Key Lab Pesticide & Chem Biol, Minist Educ,Coll Chem, 152 Luoyu Rd, Wuhan 430079, Peoples R China.
摘要:
A novel visible-light-responsive chiral ligand has been developed by grafting a triplet state photo sensitizer to chiral bisoxazoline ligands. Complexation of this ligand with Ni(acac)(2) results in a powerful catalyst for the asymmetric oxidation reaction of beta-ketoesters, which uses oxygen or air as the green oxidant and visible light or sunlight as the ideal driving force. Using this protocol, products containing the alpha-hydroxy-beta-dicarbonyl motif are produced in high yields and with excellent enantiopurities.
摘要:
A silver(I) and base-mediated [3 + 3]-cycloaddition reaction of in situ generated C,N-cyclic azomethine imines with in situ formed aza-oxyallyl cations is reported. This one-pot cycloaddition process shows broad substrate scope an excellent functional group tolerance and provides the corresponding biologically important isoquinoline-fused triazines in good to excellent yields.