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Issue 3, 2012

Highly diastereoselective and enantioselective Michael addition of 5H-oxazol-4-ones to α,β-unsaturated ketones catalyzed by a new bifunctional organocatalyst with broad substrate scope and applicability

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Abstract

A new thiourea–tertiary amine bifunctional catalyst derived from L-tert-leucine was developed and provides excellent stereocontrol in a novel and direct Michael addition of 5H-oxazol-4-ones to α,β-unsaturated ketones with much broad substrate scope. The conjugate addition products with chiral vicinal quaternary and tertiary stereocenters can be easily transformed to structurally interesting compounds or building blocks.

Graphical abstract: Highly diastereoselective and enantioselective Michael addition of 5H-oxazol-4-ones to α,β-unsaturated ketones catalyzed by a new bifunctional organocatalyst with broad substrate scope and applicability

Supplementary files

Article information


Submitted
23 Sep 2011
Accepted
29 Oct 2011
First published
11 Nov 2011

Chem. Commun., 2012,48, 461-463
Article type
Communication

Highly diastereoselective and enantioselective Michael addition of 5H-oxazol-4-ones to α,β-unsaturated ketones catalyzed by a new bifunctional organocatalyst with broad substrate scope and applicability

H. Huang, K. Zhu, W. Wu, Z. Jin and J. Ye, Chem. Commun., 2012, 48, 461 DOI: 10.1039/C1CC15928C

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