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

页码：2301 / 2305

页数：5

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