An enantioselective conjugate addition reaction of 3-substituted benzothiophen-2-ones and 2-phthalimidoacrylates

被引：8
作者：
Li, Shoulei [1 ]
Zhang, Enge [1 ]
Feng, Junjun [1 ]
Li, Xin [1 ]
机构：
[1] Nankai Univ, Collaborat Innovat Ctr Chem Sci & Engn, Coll Chem, State Key Lab Elementoorgan Chem, Tianjin 300071, Peoples R China
来源：
ORGANIC CHEMISTRY FRONTIERS | 2017年 / 4卷 / 12期
关键词：
ASYMMETRIC MICHAEL ADDITION; DIELS-ALDER REACTION; ALKYL-SUBSTITUTED THIOUREA; CONCISE TOTAL-SYNTHESIS; 1,3-DIPOLAR CYCLOADDITION; NONADJACENT STEREOCENTERS; MANZACIDIN-C; IN-SITU; BENZOFURAN-2(3H)-ONES; CONSTRUCTION;
D O I：
10.1039/c7qo00531h
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A highly enantioselective conjugate addition reaction of 3-substituted benzothiophen-2-ones to 2-phthalimidoacrylates has been developed using a bifunctional tertiary-amine thiourea catalyst. A number of chiral 3-substituted benzothiophen-2-one compounds were obtained with excellent yields (up to 99%) and very good stereoselectivities (up to > 19 : 1 dr and up to 92% ee). The reaction was proved to be an efficient strategy for the synthesis of enantioenriched a-amino acid derivatives with 1,3-nonadjacent stereogenic centers.
引用
收藏
页码：2301 / 2305
页数：5
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