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Enantioselective Cooperative Proton-Transfer Catalysis using Chiral Ammonium Phosphates

Abstract

Chiral phosphorate anions are shown to be highly en-antioselective 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 delivers remarkable enan-tioselectivity in a bioinspired, triple co-operative catal-ysis involving an achiral NHC. Thioesters with a β-chiral center can be prepared in a single step from sub-stituted cinnamaldehyde derivatives, with up to 99% yield and 99% ee. Heteroaryl groups are well tolerated in these reactions, despite the presence of basic sites.

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Publication details

The article was received on 14 Dec 2017, accepted on 10 Jan 2018 and first published on 10 Jan 2018


Article type: Communication
DOI: 10.1039/C7CC09549J
Citation: Chem. Commun., 2018, Accepted Manuscript
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    Enantioselective Cooperative Proton-Transfer Catalysis using Chiral Ammonium Phosphates

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

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