Diastereoselective Spirocyclization of Benzoxazines with Nitroalkenes via Rhodium-Catalyzed C-H Functionalization/Annulation Cascade under Mild Conditions

被引：29

作者：

Mishra, Aniket ^{[1
]}

Bhowmik, Arup ^{[1
]}

Samanta, Siddhartha ^{[1
]}

Sarkar, Writhabrata ^{[1
]}

Das, Sumit ^{[1
]}

Deb, Indubhusan ^{[1
]}

机构：

[1] CSIR Indian Inst Chem Biol, Organ & Med Chem Div, Kolkata 700032, India

来源：

ORGANIC LETTERS | 2020年 / 22卷 / 04期

关键词：

N-SULFONYL KETIMINES; 3+2 ANNULATION; ANTIBACTERIAL ACTIVITIES; ACYL KETIMINES; DERIVATIVES; ACTIVATION; ACETOXYLATION; 1,3-DIENES; NITRATION; OLEFINS;

D O I：

10.1021/acs.orglett.9b04652

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A Rh(III)-catalyzed [3 + 2] annulation of benzoxazines with nitroolefins that proceeds via redox-neutral C-H functionalization has been demonstrated, leading to the novel class of spirocycles in a single step. The construction of three continuous stereogenic centers has been achieved starting from easily accessible achiral substrates in an atom-efficient manner under mild reaction conditions. A broad range of pharmaceutically relevant nitro substituted spirocyclic 2,3-dihydro-1,4-benzoxazine derivatives has been synthesized in good to excellent yields with high diastereoselectivity.

引用

页码：1340 / 1344

页数：5

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