Chiral 1,3-aminosquaramides derived from cis-2-benzamidocyclohexanecarboxylic acid as organocatalysts for asymmetric Michael addition reactions

被引：2

作者：

Kodama, Koichi ^{[1
]}

Maruyama, Kazuhisa ^{[1
]}

Hirose, Takuji ^{[1
]}

机构：

[1] Saitama Univ, Grad Sch Sci & Engn, Sakura Ku, 255 Shimo Okubo, Saitama 3388570, Japan

来源：

TETRAHEDRON | 2022年 / 112卷

关键词：

Asymmetric synthesis; Organocatalyst; Squaramide; Chirality; Michael addition; CATALYZED CONJUGATE ADDITION; 1,3-DICARBONYL COMPOUNDS; ENANTIOSELECTIVE SYNTHESIS; SQUARAMIDES; ALDEHYDES;

D O I：

10.1016/j.tet.2022.132750

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Herein, chiral 1,3-aminosquaramides derived from cis-2-benzamidocyclohexanecarboxylic acid, which is a chiral beta-amino acid derivative, were synthesized and applied as bifunctional organocatalysts for asymmetric Michael addition reaction of 1,3-dicarbonyl compounds to beta-nitrostyrenes. The catalyst structure and reaction conditions, such as solvent and temperature, were examined, and then, the optimized organocatalyst was successfully applied to the reaction of 1,3-diketones and 1,3-ketoesters with an enantioselectivity of up to 96%. Plausible transition state was proposed based on the results reported in previous reports and DFT calculations.

引用

页数：6

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