Diastereo- and enantioselective additions of α-nitro esters to imines for -α,β-diamino acid synthesis with α-alkyl-substitution.

Chem Sci

Department of Chemistry , Vanderbilt Institute of Chemical Biology , Vanderbilt University, Nashville , Tennessee 37235 , USA . Email:

Published: February 2018

The discovery that a -symmetric bis(AMidine) [BAM] catalyst promotes an -selective addition of α-substituted α-nitro esters to imines is described, providing α-substituted α,β-diamino ester products with high diastereo- and enantioselectivity. When compared to the function of a BAM catalyst reported previously, the pair offer a rare example of diastereodivergence using a bifunctional Brønsted acid-base organocatalyst.

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Source
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC5903423PMC
http://dx.doi.org/10.1039/c7sc05176jDOI Listing

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