Enantioselective Synthesis of 1,3-Benzothiazine Derivatives: An Organocatalytic Chemoselective Approach

被引：8

作者：

Gayen, Prasenjit ^{[1
]}

Ghorai, Prasanta ^{[1
]}

机构：

[1] Indian Inst Sci Educ & Res IISER Bhopal, Dept Chem, Bhopal 462066, India

来源：

ORGANIC LETTERS | 2023年 / 25卷 / 21期

关键词：

SULFA-MICHAEL ADDITION; MICHAEL/MICHAEL ADDITION; ASYMMETRIC-SYNTHESIS; ACID-DERIVATIVES; CASCADE; THIOLS; CHROMANS; CATALYST; ACCESS;

D O I：

10.1021/acs.orglett.3c01120

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Herein, a highly chemoselective 1,2-additionof thiols with 2-isothiocyanatochalconesfollowed by an enantioselective intramolecular thia-Michael additioncascade has been established to construct enantioenriched [1,3]-benzothiazinederivatives for the first time. The cinchona-derived squaramide catalystprovides good to excellent yield and enantioselectivity of the productswith broad substrate adaptability. Furthermore, this strategy hasbeen extended to the diphenylphosphine oxide nucleophile to accessenantioenriched organophosphorus-substituted [1,3]-benzothazines.A scale-up reaction and synthetic transformation have demonstratedthe viability of this protocol.

引用

页码：3835 / 3840

页数：6

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