Organocatalytic Asymmetric Synthesis of Spirooxindole Embedded Oxazolidines

被引：11
|
作者：
Parida, Chandrakanta [1 ]
Mondal, Buddhadeb [1 ]
Ghosh, Animesh [1 ]
Pan, Subhas Chandra [1 ]
机构：
[1] Indian Inst Technol Guwahati, Dept Chem, North Guwahati 781039, Assam, India
来源：
JOURNAL OF ORGANIC CHEMISTRY | 2021年 / 86卷 / 18期
关键词：
FORMAL 3+2 CYCLOADDITION; ENANTIOSELECTIVE CONSTRUCTION; MICHAEL ADDITION; AZOMETHINE YLIDE; 1,3-OXAZOLIDINES; CASCADE; CYCLIZATION; ISATINS; IMINES; ESTERS;
D O I：
10.1021/acs.joc.1c00644
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The first organocatalytic asymmetric synthesis of spirooxindole embedded oxazolidines has been developed via a domino reaction involving hemiaminal formation, followed by an unprecedented aza-Michael reaction between isatin derived N-Boc ketimines and gamma-hydroxy enones. A quinine derived bifunctional squaramide catalyst was found to be efficient for this reaction, and the products were obtained in good diastereoselectivity and with high enantioselectivity.
引用
收藏
页码：13082 / 13091
页数：10
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