Highly Enantioselective Michael Addition of Cyclic Diketones to β,γ-Unsaturated α-Keto Esters Catalyzed by Squaramide Organocatalyst

Zhi-Wei Ma; Chuan-Chuan Wang; Xiao-Pei Chen; Ai-Qin Li; Jing-Chao Tao; Quan-Jian Lv

doi:10.1055/s-0040-1719863

Synthesis, Table of Contents

Synthesis 2022; 54(07): 1785-1792
DOI: 10.1055/s-0040-1719863

paper

Highly Enantioselective Michael Addition of Cyclic Diketones to β,γ-Unsaturated α-Keto Esters Catalyzed by Squaramide Organocatalyst

Authors

Zhi-Wei Ma∗

^aFaculty of Science, Henan University of Animal Husbandry and Economy, No. 146 Yingcai Street, Zhengzhou 450046, P. R. of China
Chuan-Chuan Wang‡

^aFaculty of Science, Henan University of Animal Husbandry and Economy, No. 146 Yingcai Street, Zhengzhou 450046, P. R. of China
Xiao-Pei Chen

^aFaculty of Science, Henan University of Animal Husbandry and Economy, No. 146 Yingcai Street, Zhengzhou 450046, P. R. of China
Ai-Qin Li

^aFaculty of Science, Henan University of Animal Husbandry and Economy, No. 146 Yingcai Street, Zhengzhou 450046, P. R. of China
Jing-Chao Tao

^bCollege of Chemistry, Zhengzhou University, No. 100 Science Avenue, Zhengzhou 450001, P. R. of China
Quan-Jian Lv∗

^aFaculty of Science, Henan University of Animal Husbandry and Economy, No. 146 Yingcai Street, Zhengzhou 450046, P. R. of China

Abstract

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Abstract

A new tertiary amine-squaramide organocatalyst has been developed and applied to the asymmetric Michael addition of cyclic diketones to β,γ-unsaturated α-keto esters. 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 in high yields (up to 97%) with excellent enantioselectivities (up to 99 % ee). Furthermore, this catalytic system can be used efficiently in large-scale reactions with the yields and enantioselectivities being maintained.

Key words

Michael addition - organocatalysis - tertiary amine-squaramide - cyclic diketone - β,γ-unsaturated α-keto esters

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References

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Supplementary Material

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