Organocatalytic Enantioselective Synthesis of 1,3-Oxazinanes and Hexahydropyrimidines via [4+2]-Annulation of Cyclic N-Sulfimines

被引：3

作者：

Kim, Seung Yeon ^{[1
]}

Kim, Yoseop ^{[1
]}

Kim, Sung-Gon ^{[1
]}

机构：

[1] Kyonggi Univ, Dept Chem, 154-42 Gwanggyosan Ro, Suwon 16227, South Korea

来源：

ASIAN JOURNAL OF ORGANIC CHEMISTRY | 2023年 / 12卷 / 05期

基金：

新加坡国家研究基金会;

关键词：

4+2]-annulation; cyclic N-sulfimine; hexahydropyrimidine; imidazolidine; oranocatalysis; ASYMMETRIC-SYNTHESIS; ANNULATION; ALKALOIDS; KETONES; RING;

D O I：

10.1002/ajoc.202300022

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The first asymmetric synthetic method for enantioenriched 1,3-oxazinane and hexahydropyrimidine derivatives via the asymmetric [4+2]-annulation of cyclic N-sulfimines has been established. The reaction of cyclic N-sulfimines with delta-hydroxy-alpha,beta-unsaturated ketones afforded a wide range of enantioenriched polyheterotricyclic 1,3-oxazinane derivatives in high yields with good to excellent enantioselectivities in the presence of a cinchonidine-derived squaramide catalyst. This approach has been extended to the asymmetric organocatalytic [4+2]-annulation of cyclic N-sulfimines with delta-NHTs-alpha,beta-unsaturated ketones providing enantioenriched hexahydropyrimidines. In addition, the asymmetric [4+2]-annulation of delta-hydroxy- and delta-NHTs-alpha,beta-unsaturated ketones gave their corresponding enantioenriched 1,3-oxazinane and hexahydropyrimidine derivatives with different absolute configurations.

引用

页数：6

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