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Letters in Organic Chemistry

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ISSN (Print): 1570-1786
ISSN (Online): 1875-6255

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Short Communication

Amine-Squaramide Catalyzed Asymmetric Michael Addition of Cyclic Diketones and β,γ-unsaturated α-keto Esters

Author(s): Zhi-Jing Liu, Zhi-Wei Ma*, Xiao-Pei Chen, Chuan-Chuan Wang, Jun-Tao Liu and Jing-Chao Tao

Volume 19, Issue 11, 2022

Published on: 29 April, 2022

Page: [1042 - 1046] Pages: 5

DOI: 10.2174/1570178619666220314152530

Price: $65

Abstract

A novel tertiary amine squaramide has been successfully developed and applied to catalyze the asymmetric Michael addition between cyclic diketones and β,γ-unsaturated α-ketoesters. The catalyst system performed well with a low catalyst loading of 1 mol% under mild reaction conditions. A series of synthetically and pharmaceutically useful chiral bicyclic compounds were obtained with both high yields (up to 97%) and excellent enantioselectivities (up to 97% ee).

Keywords: Michael addition, organocatalysis, tertiary amine-squaramide, cyclic diketone, βγ-unsaturated α-ketoesters, isosteviol derivative.

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