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

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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