Catalytic Asymmetric Conjugate Addition of Thiols to α,β-Unsaturated Thioamides: Expeditious Access to Enantioenriched 1,5-Benzothiazepines

被引：43

作者：

Ogawa, Takanori ^{[1
]}

Kumagai, Naoya ^{[1
]}

Shibasaki, Masakatsu ^{[1
]}

机构：

[1] Inst Microbial Chem, Shinagawa Ku, Tokyo 1410021, Japan

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2012年 / 51卷 / 34期

关键词：

1; 5-benzothiazepine; asymmetric catalysis; chemoselectivity; conjugate addition; synthetic methods; SULFA-MICHAEL ADDITION; N-ACYLATED OXAZOLIDIN-2-ONES; CHIRAL LEWIS-ACID; ENANTIOSELECTIVE PROTONATION; CARBONYL-COMPOUNDS; TERMINAL ALKYNES; TRANSFORMATIONS; CONSTRUCTION; ACTIVATION; THIOPHENOL;

D O I：

10.1002/anie.201204365

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Softly does it: The title reaction proceeded under proton transfer conditions with a catalyst prepared from commercially available reagents to afford the desired product in high enantioselectivity. The reaction was compatible with a free amino group, thus allowing for expeditious access to enantiomerically enriched 1,5-benzothiazepines, which are important chemical entities in medicinal chemistry.

引用

页码：8551 / 8554

页数：4

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