Highly Enantioselective Iridium-Catalyzed Coupling Reaction of Vinyl Azides and Racemic Allylic Carbonates

被引：173

作者：

Han, Min ^{[1
]}

Yang, Min ^{[1
]}

Wu, Rui ^{[1
]}

Li, Yang ^{[1
]}

Jia, Tao ^{[1
]}

Gao, Yuanji ^{[1
]}

Ni, Hai-Liang ^{[1
]}

Hu, Ping ^{[1
]}

Wang, Bi-Qin ^{[1
]}

Cao, Peng ^{[1
]}

机构：

[1] Sichuan Normal Univ, Coll Chem & Mat Sci, Chengdu 610068, Sichuan, Peoples R China

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2020年 / 142卷 / 31期

关键词：

NEGATIVE ALLOSTERIC MODULATOR; ALPHA-AMINO-ACIDS; CONJUGATE ADDITIONS; AMIDE SYNTHESIS; ALKYLATION; SUBSTITUTION; ALLYLATION; DIASTEREOSELECTIVITY; NUCLEOPHILE; DERIVATIVES;

D O I：

10.1021/jacs.0c01766

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The iridium-catalyzed enantioselective coupling reaction of vinyl azides and allylic electrophiles is presented and provides access to beta-chiral carbonyl derivatives. Vinyl azides are used as acetamide enolate or acetonitrile carbanion surrogates, leading to gamma, delta-unsaturated beta-substituted amides as well as nitriles with excellent enantiomeric excess. These products are readily transformed into chiral N-containing building blocks and pharmaceuticals. A mechanism is proposed to rationalize the chemoselectivity of this coupling reaction.

引用

页码：13398 / 13405

页数：8

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