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Issue 42, 2012

Organocatalytic asymmetric oxy-Michael addition to a γ-hydroxy-α,β-unsaturated thioesterviahemiacetal intermediates

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Abstract

We report an asymmetric oxy-Michael addition to a γ-hydroxy-α,β-unsaturated thioester via hemiacetal intermediates in the presence of Cinchona-alkaloid-thiourea-based bifunctional organocatalysts. This method provides a novel enantioselective route to β-hydroxy carboxyl compounds, which in turn can be used to synthesize valuable chiral building blocks.

Graphical abstract: Organocatalytic asymmetric oxy-Michael addition to a γ-hydroxy-α,β-unsaturated thioester via hemiacetal intermediates

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Article information


Submitted
03 Mar 2012
Accepted
23 Mar 2012
First published
26 Mar 2012

Chem. Commun., 2012,48, 5076-5078
Article type
Communication

Organocatalytic asymmetric oxy-Michael addition to a γ-hydroxy-α,β-unsaturated thioester via hemiacetal intermediates

T. Okamura, K. Asano and S. Matsubara, Chem. Commun., 2012, 48, 5076 DOI: 10.1039/C2CC31602A

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