Issue 12, 2017

Ir/PTC cooperatively catalyzed asymmetric umpolung allylation of α-imino ester enabled synthesis of α-quaternary amino acid derivatives bearing two vicinal stereocenters

Abstract

A novel Ir/PTC (phase-transfer catalyst) cooperatively catalyzed asymmetric umpolung allylation of simple α-imino esters is developed and it provides facile access to α-quaternary amino acid derivatives bearing two vicinal stereocenters. Both the metal catalyst and the phase-transfer catalyst are crucial for this methodology. The reaction features good yields, high diastereo- and enantio-selectivities, ease of scale-up to gram scale and further transformation of the products (e.g. to quaternary proline analogues with multi stereocenters).

Graphical abstract: Ir/PTC cooperatively catalyzed asymmetric umpolung allylation of α-imino ester enabled synthesis of α-quaternary amino acid derivatives bearing two vicinal stereocenters

Supplementary files

Article information

Article type
Communication
Submitted
06 Dec 2016
Accepted
16 Jan 2017
First published
16 Jan 2017

Chem. Commun., 2017,53, 1985-1988

Ir/PTC cooperatively catalyzed asymmetric umpolung allylation of α-imino ester enabled synthesis of α-quaternary amino acid derivatives bearing two vicinal stereocenters

Y. Su, Y. Li, Y. Chen and Z. Han, Chem. Commun., 2017, 53, 1985 DOI: 10.1039/C6CC09654A

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