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Issue 22, 2014
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Peptide-catalyzed consecutive 1,6- and 1,4-additions of thiols to α,β,γ,δ-unsaturated aldehydes

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Abstract

Regio- and enantioselective addition of thiols to α,β,γ,δ-unsaturated aldehydes was performed with a resin-supported peptide catalyst. It was shown that a 1,4-adduct was generated mainly at the initial stage of the reaction, and this was eventually converted to a thermodynamically stable 1,6- and 1,4-diadduct through retro-addition/addition reactions.

Graphical abstract: Peptide-catalyzed consecutive 1,6- and 1,4-additions of thiols to α,β,γ,δ-unsaturated aldehydes

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Article information


Submitted
14 Mar 2014
Accepted
17 Apr 2014
First published
17 Apr 2014

Org. Biomol. Chem., 2014,12, 3581-3585
Article type
Communication
Author version available

Peptide-catalyzed consecutive 1,6- and 1,4-additions of thiols to α,β,γ,δ-unsaturated aldehydes

K. Akagawa, N. Nishi, J. Sen and K. Kudo, Org. Biomol. Chem., 2014, 12, 3581
DOI: 10.1039/C4OB00565A

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