Issue 8, 2018

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

Abstract

The discovery that a C2-symmetric bis(AMidine) [BAM] catalyst promotes an anti-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.

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

Supplementary files

Article information

Article type
Edge Article
Submitted
05 Dec 2017
Accepted
23 Jan 2018
First published
31 Jan 2018
This article is Open Access

All publication charges for this article have been paid for by the Royal Society of Chemistry
Creative Commons BY license

Chem. Sci., 2018,9, 2336-2339

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

D. J. Sprague, A. Singh and J. N. Johnston, Chem. Sci., 2018, 9, 2336 DOI: 10.1039/C7SC05176J

This article is licensed under a Creative Commons Attribution 3.0 Unported Licence. You can use material from this article in other publications without requesting further permissions from the RSC, provided that the correct acknowledgement is given.

Read more about how to correctly acknowledge RSC content.

Social activity

Spotlight

Advertisements