Synthesis of Chiral Tetrasubstituted Azetidines from Donor-Acceptor Azetines via Asymmetric Copper(I)-Catalyzed Imido-Ylide [3+1]-Cycloaddition with Metallo-Enolcarbenes

被引：41

作者：

Marichev, Kostiantyn O. ^{[1
]}

Wang, Kan ^{[1
]}

Dong, Kuiyong ^{[1
]}

Greco, Nicole ^{[1
]}

Massey, Lynee A. ^{[1
]}

Deng, Yongming ^{[1
]}

Arman, Hadi ^{[1
]}

Doyle, Michael P. ^{[1
]}

机构：

[1] Univ Texas San Antonio, Dept Chem, One UTSA Circle, San Antonio, TX 78249 USA

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2019年 / 58卷 / 45期

基金：

美国国家科学基金会; 中国国家自然科学基金;

关键词：

azetidines; azetines; copper catalysis; cycloaddition; hydrogenation; GLYCOSIDASE INHIBITORY-ACTIVITY; CYCLOADDITION REACTIONS; PENARESIDIN-B; ACID; PHYTOSIDEROPHORES; IMINOSUGARS; NICOTIANAMINE; BIOSYNTHESIS; AMINATION; CHEMISTRY;

D O I：

10.1002/anie.201909929

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The all-cis stereoisomers of tetrasubstituted azetidine-2-carboxylic acids and derivatives that possess three chiral centers have been prepared in high yield and stereocontrol from silyl-protected Z-gamma-substituted enoldiazoacetates and imido-sulfur ylides by asymmetric [3+1]-cycloaddition using chiral sabox copper(I) catalysis followed by Pd/C catalytic hydrogenation. Hydrogenation of the chiral p-methoxybenzyl azetine-2-carboxylates occurs with both hydrogen addition to the C=C bond and hydrogenolysis of the ester.

引用

页码：16188 / 16192

页数：5

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