Catalyst-Free Stereocontrolled Formal [3+2]-Cycloaddition of CO2 for the Synthesis of Enantiopure Spiro[indoline-3,5′-oxazolidine]-2,2′-diones under Aqueous and Ambient Conditions

被引：16

作者：

Hajra, Saumen ^{[1
]}

Biswas, Anurag ^{[1
]}

机构：

[1] Sanjay Gandhi Postgrad Inst Med Sci Campus, Ctr Biomed Res, Lucknow 226014, Uttar Pradesh, India

来源：

ORGANIC LETTERS | 2020年 / 22卷 / 13期

关键词：

CARBON-DIOXIDE; CHEMICAL FIXATION; TRANSFORMATION; CYCLOADDITION; AZIRIDINES; COMPLEX;

D O I：

10.1021/acs.orglett.0c01526

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A highly efficient regio- and stereoselective spontaneous formal [3 + 2]-cycloaddition of CO2 in aqueous medium is developed for the one-pot synthesis of spiro[indoline-3,5'-oxazolidine]-2,2'-diones with excellent enantiopuirity (ee up to 99%) under catalyst-free and ambient conditions. The detailed study reveals NH-spiroaziridine- and 3-(aminomethyl)-3-chloro-oxindoles, two in situ generated reactive intermediate compounds for the spontaneous cycloaddition with CO2, and the latter is responsible for the stereoselectivity. An unprecedented mechanism of desulfinylation is also disclosed herewith.

引用

页码：4990 / 4994

页数：5

共 29 条

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