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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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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., 2018,54, 1473-1476
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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, 54, 1473
    DOI: 10.1039/C7CC09549J

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