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Synthesis 2017; 49(06): 1307-1314
DOI: 10.1055/s-0036-1588090
DOI: 10.1055/s-0036-1588090
paper
Chiral Primary Amine–Squaramide Catalyzed Highly Enantioselective Michael Addition of Isobutyraldehyde to Nitroolefins
Further Information
Publication History
Received: 31 August 2016
Accepted after revision: 14 October 2016
Publication Date:
22 November 2016 (online)
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 - enantiomersSupporting Information
- Supporting information for this article is available online at http://dx.doi.org/10.1055/s-0036-1588090.
- Supporting Information
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