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Issue 12, 2017
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Ir/PTC cooperatively catalyzed asymmetric umpolung allylation of α-imino ester enabled synthesis of α-quaternary amino acid derivatives bearing two vicinal stereocenters

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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

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Article information


Submitted
06 Dec 2016
Accepted
16 Jan 2017
First published
16 Jan 2017

Chem. Commun., 2017,53, 1985-1988
Article type
Communication

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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