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Issue 12, 2018
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Enantioselective cooperative proton-transfer catalysis using chiral ammonium phosphates

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Abstract

Chiral phosphorate anions are shown to be highly enantioselective templates for proton-transfer catalysis. A salt generated in situ from a bridgehead amine and a BINOL-derived chiral phosphoric acid serves as an effective proton-shuttle that exhibits remarkable enantioselectivity in a bioinspired, triple co-operative catalysis involving an achiral NHC. Thioesters with a β-chiral center can be prepared in a single step from substituted cinnamaldehyde derivatives, with up to 99% yield and 99% ee. Heteroaryl groups are well tolerated in these reactions, despite the presence of basic sites.

Graphical abstract: Enantioselective cooperative proton-transfer catalysis using chiral ammonium phosphates

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Supplementary files

Article information


Submitted
14 Dec 2017
Accepted
10 Jan 2018
First published
10 Jan 2018

Chem. Commun., 2018,54, 1473-1476
Article type
Communication

Enantioselective cooperative proton-transfer catalysis using chiral ammonium phosphates

L. Zhang, P. Yuan, J. Chen and Y. Huang, Chem. Commun., 2018, 54, 1473
DOI: 10.1039/C7CC09549J

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