Formal [3+4] Annulation of α,β-Unsaturated Acyl Azoliums: Access to Enantioenriched N-H-Free 1,5-Benzothiazepines

被引：63

作者：

Fang, Chao ^{[1
]}

Lu, Tao ^{[1
]}

Zhu, Jindong ^{[1
]}

Sun, Kewen ^{[1
]}

Du, Ding ^{[1
]}

机构：

[1] China Pharmaceut Univ, Dept Organ Chem, State Key Lab Nat Med, Nanjing 210009, Jiangsu, Peoples R China

来源：

ORGANIC LETTERS | 2017年 / 19卷 / 13期

基金：

中国国家自然科学基金;

关键词：

HIGHLY ENANTIOSELECTIVE SYNTHESIS; HETEROCYCLIC CARBENE CATALYSIS; ALKYNYL ALDEHYDES; 1,3-DICARBONYL COMPOUNDS; EXPEDITIOUS ACCESS; MICHAEL ADDITION; ENALS; BROMOENALS; CYCLOADDITION; ESTERS;

D O I：

10.1021/acs.orglett.7b01457

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An unprecedented formal [3 + 4] annulation of alpha,beta-unsaturated acyl azoliums with 2-aminobenzenethiols has been utilized to synthesize enantioenriched N-H-free 1,5-benzothiazepines, which are recognized as privileged structures in numerous biologically active scaffolds. This protocol offers a rapid and direct pathway to access the target compounds with high enantioselectivities and has been applied in the concise synthesis of chiral drug (R)-thiazesim.

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收藏

页码：3470 / 3473

页数：4

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