Asymmetric catalytic nitrooxylation and azidation of β-keto amides/esters with hypervalent iodine reagents

被引：14

作者：

He, Changqiang ^{[1
]}

Wu, Zhikun ^{[1
]}

Zhou, Yuqiao ^{[1
]}

Cao, Weidi ^{[1
]}

Feng, Xiaoming ^{[1
]}

机构：

[1] Sichuan Univ, Coll Chem, Key Lab Green Chem & Technol, Minist Educ, Chengdu 610064, Peoples R China

来源：

ORGANIC CHEMISTRY FRONTIERS | 2022年 / 9卷 / 03期

基金：

中国国家自然科学基金;

关键词：

TERT-BUTYL NITRITE; NITRATE ESTERS; ORGANIC AZIDES; OXIDE; EFFICIENT; ALCOHOLS; EPOXIDES; CYCLOADDITION; OXIDATION; CHEMISTRY;

D O I：

10.1039/d1qo01634b

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Chiral Lewis acid-catalyzed enantioselective nitrooxylation of cyclic and acyclic beta-keto amides/esters with hypervalent iodine(iii) reagents is reported. A number of alpha-nitrooxy-beta-keto amides/esters were obtained with good yields and high enantioselectivities by using bench-stable nitratobenziodoxole under mild conditions. This methodology was also applied to azidation and produced alpha-azido-beta-keto amides/esters with high enantioselectivities (up to 97% ee).

引用

页码：703 / 708

页数：6

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