Chiral Primary Amine–Squaramide Catalyzed Highly Enantio­selective Michael Addition of Isobutyraldehyde to Nitroolefins

Zhi-Wei Ma; Xiao-Feng Liu; Bin Sun; Xian-Hui Huang; Jing-Chao Tao

doi:10.1055/s-0036-1588090

Synthesis, Table of Contents

Synthesis 2017; 49(06): 1307-1314
DOI: 10.1055/s-0036-1588090

paper

Chiral Primary Amine–Squaramide Catalyzed Highly Enantioselective Michael Addition of Isobutyraldehyde to Nitroolefins

Zhi-Wei Ma*

^aDepartment of Fundamental Courses, Henan University of Animal Husbandry and Economy, No. 2 Yingcai Street, Huiji District, Zhengzhou 450044, Henan, P. R. of China Email: mazhiwei1986@126.com

,

Xiao-Feng Liu

^bCollege of Chemistry and Molecular Engineering, Zhengzhou University, No. 100 Science Avenue, High-Tech Zone, Zhengzhou 450001, Henan, P. R. of China Email: jctao@zzu.edu.cn

,

Bin Sun

^bCollege of Chemistry and Molecular Engineering, Zhengzhou University, No. 100 Science Avenue, High-Tech Zone, Zhengzhou 450001, Henan, P. R. of China Email: jctao@zzu.edu.cn

,

Xian-Hui Huang

^bCollege of Chemistry and Molecular Engineering, Zhengzhou University, No. 100 Science Avenue, High-Tech Zone, Zhengzhou 450001, Henan, P. R. of China Email: jctao@zzu.edu.cn

,

Jing-Chao Tao*

^bCollege of Chemistry and Molecular Engineering, Zhengzhou University, No. 100 Science Avenue, High-Tech Zone, Zhengzhou 450001, Henan, P. R. of China Email: jctao@zzu.edu.cn

› Author Affiliations

Abstract

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Abstract

Chiral primary amine–squaramides have not been extensively studied to date in the field of organocatalysis. In this paper, novel chiral squaramides derived from natural product stevioside were developed. Both enantiomers of a series of γ-nitroaldehydes were generated by using these squaramide catalysts for the Michael addition reaction of isobutyraldehyde to nitroolefins. This asymmetric reaction proceeded well to afford the desired products in high yields (up to 98%) with high to excellent enantioselectivities (up to 99% ee).

Key words

primary amine–squaramide - isobutyraldehyde - nitroolefin - Michael addition - enantiomers

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Supplementary Material

Supporting Information

Chiral Primary Amine–Squaramide Catalyzed Highly Enantio­selective Michael Addition of Isobutyraldehyde to Nitroolefins

Chiral Primary Amine–Squaramide Catalyzed Highly Enantioselective Michael Addition of Isobutyraldehyde to Nitroolefins