Asymmetric Synthesis of Enantioenriched 2-Aryl-2,3-Dihydrobenzofurans by a Lewis Acid Catalyzed Cyclopropanation/Intramolecular Rearrangement Sequence

被引：36
|
作者：
Pandit, Rameshwar Prasad [1 ]
Kim, Seung Tae [1 ]
Ryu, Do Hyun [1 ]
机构：
[1] Sungkyunkwan Univ, Dept Chem, 300 Cheoncheon, Suwon 16419, South Korea
来源：
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2019年 / 58卷 / 38期
基金：
新加坡国家研究基金会;
关键词：
2; 3-dihydrobenzofuran; diazoester; ortho-quinone methide; quaternary carbon atoms; rearrangement; C-H INSERTION; ORTHO-QUINONE METHIDE; DONOR-ACCEPTOR CYCLOPROPANES; RING-OPENING CYCLIZATION; ENANTIOSELECTIVE SYNTHESIS; STEREOSELECTIVE-SYNTHESIS; 3+2 ANNULATION; CONSTRUCTION; DIAZOESTERS; AMINOCYCLOPROPANES;
D O I：
10.1002/anie.201906954
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
A cyclopropanation/intramolecular rearrangement initiated by the Michael addition of in situ generated ortho-quinone methides (o-QMs) has been developed for the enantioselective synthesis of 2-aryl-2,3-dihydrobenzofurans containing two consecutive stereogenic centers, including a quaternary carbon atom. In the presence of a chiral oxazaborolidinium ion catalyst, the reaction proceeded in excellent yields (up to 95 %) with excellent stereoselectivity (up to >99 ee, up to >20:1 d.r.).
引用
收藏
页码：13427 / 13432
页数：6
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