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Catalytic Asymmetric Synthesis of Chiral Dihydrobenzofurans through a Formal [4+1] Annulation Reaction of Sulfur Ylides and In Situ Generated ortho-Quinone Methides

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成果类型:
期刊论文
作者:
Yang, Qing-Qing*;Xiao, Wen-Jing
通讯作者:
Yang, Qing-Qing
作者机构:
[Yang, Qing-Qing] China Three Gorges Univ, Coll Mat & Chem Engn, Key Lab Inorgan Nonmetall Crystalline & Energy Co, 8 Daxue Rd, Yichang 443002, Hubei, Peoples R China.
[Yang, Qing-Qing; 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:
[Yang, Qing-Qing] C
China Three Gorges Univ, Coll Mat & Chem Engn, Key Lab Inorgan Nonmetall Crystalline & Energy Co, 8 Daxue Rd, Yichang 443002, Hubei, Peoples R China.
Cent China Normal Univ, Key Lab Pesticide & Chem Biol, Minist Educ, Coll Chem, 152 Luoyu Rd, Wuhan 430079, Hubei, Peoples R China.
语种:
英文
关键词:
Asymmetric catalysis;Hydrogen bonds;Homogeneous catalysis;Ylides;Annulation
期刊:
European Journal of Organic Chemistry
ISSN:
1434-193X
年:
2017
卷:
2017
期:
2
页码:
233-236
基金类别:
China Three Gorges University; National Natural Science Foundation of ChinaNational Natural Science Foundation of China (NSFC) [21232003, 21202053, 21272087]; National Basic Research Program of ChinaNational Basic Research Program of China [2011CB808603]
机构署名:
本校为通讯机构
院系归属:
化学学院
摘要:
The first example of a catalytic asymmetric formal [4+1] annulation reaction between sulfur ylides and in situ generated ortho-quinone methides (o-QMs) is reported in this work. A C2-symmetric chiral urea was identified to be the best H-bonding catalyst, affording a wide range of chiral 2,3-dihydrobenzofurans in high yields and moderate enantioselectivities [70–98 % yields, up to 89:11 e.r. (enantiomeric ratio)]. ©...

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