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Phosphine-Catalyzed Atroposelective Formal [3+2] Cycloaddition Desymmetrization of N-Arylmaleimides

delete2022-09-07
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PRE
AI
王华敏 cover
王华敏 (Huamin Wang)
Y
Yibo Wei
Y
Yuqiang Li
S
Shuangshuang Long
李石雄 cover
李石雄 (Shixiong Li)
Y
Ying‐Wu Lin *
DOI:10.1021/acs.orglett.2c02208delete
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Abstract

Abstract

En 中文
Herein, a new strategy for the enantioselective synthesis of axially chiral N-aryl succinimides was devised by [3 + 2] annulation of MBH carbonates and N-aryl maleimides under chiral phosphine. This desymmetrization process allows for quick construction of both two stereogenic carbon centers and a remote C-Ar-N atropisomeric chirality. A series of structurally diverse N-aryl succinimides were obtained with good to excellent yields, diastereoselectivities, and enantioselectivities. The process is mild, efficient, and scalable and features a broad substrate scope.
Keywords:
MORITA-BAYLIS-HILLMAN
ASYMMETRIC CONSTRUCTION
LIGANDS
ANNULATION
RESOLUTION
CARBONATES
DESIGN

Journal

Organic Letters cover
Organic Letters
IF:
5
Papers:
3.9W
Citations:
10.0W

Organization

C
Central South University
Scholars:
10.0W
Papers: 7.2W
Citations: 10.9W
U
university of south china
Scholars:
1.4W
Papers: 6.8K
Citations: 8