Asymmetric catalytic alkynylation of thiazolones and azlactones for synthesis of quaternary α-amino acid precursors

被引：11

作者：

Meng, Beibei ^{[1
,2
]}

Shi, Qian ^{[1
,2
]}

Meng, Yuan ^{[1
,2
]}

Chen, Jie ^{[1
,2
]}

Cao, Weiguo ^{[1
,2
]}

Wu, Xiaoyu ^{[1
,2
]}

机构：

[1] Shanghai Univ, Ctr Supramol Chem & Catalysis, 99 Shangda Lu, Shanghai 200444, Peoples R China

[2] Shanghai Univ, Coll Sci, Dept Chem, 99 Shangda Lu, Shanghai 200444, Peoples R China

来源：

ORGANIC & BIOMOLECULAR CHEMISTRY | 2021年 / 19卷 / 23期

基金：

中国国家自然科学基金;

关键词：

HYPERVALENT IODINE REAGENTS; HIGHLY ENANTIOSELECTIVE CONSTRUCTION; PHASE-TRANSFER CATALYSTS; MICHAEL ADDITION; ALKYLATION; DERIVATIVES; ALLYLATION; RECEPTOR; TERTIARY; DIASTEREOSELECTIVITY;

D O I：

10.1039/d1ob00582k

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Asymmetric alkynylation of thiazolones and azlactones with alkynylbenziodoxolones as the electrophilic alkyne source catalyzed by thiourea phosphonium salt is described. By using thiazolones as nucleophiles, the desired alkyne functionalized thiazolones were obtained in 55-89% yields with 31-86% ee. Azlactones gave the desired products in comparable yields with lower enantioselectivities. Ring-opening of the alkynylation products led to alpha,alpha-disubstituted alpha-amino acid derivatives efficiently without loss of enantioselectivity.

引用

页码：5087 / 5092

页数：6

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