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Issue 24, 2018
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Chemoselective phosphine-catalyzed cyanoacylation of α-dicarbonyl compounds: a general method for the synthesis of cyanohydrin esters with one quaternary stereocenter

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Abstract

A chemoselective phosphine-catalyzed cyanoacylation of α-dicarbonyl compounds is reported. Under the catalysis of P(NMe2)3, the cyanoacylation of α-dicarbonyl compounds such as isatins, α-keto esters, and α-diketones with acyl cyanides exclusively proceeds under very mild conditions, affording a wide range of cyanohydrin esters bearing one quaternary stereocenter in moderate to excellent yields. It represents the first phosphine-catalyzed cyanoacylation of α-dicarbonyl compounds and also provides a general method to prepare fully substituted cyanohydrin esters.

Graphical abstract: Chemoselective phosphine-catalyzed cyanoacylation of α-dicarbonyl compounds: a general method for the synthesis of cyanohydrin esters with one quaternary stereocenter

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Publication details

The article was received on 25 Sep 2018, accepted on 01 Nov 2018 and first published on 01 Nov 2018


Article type: Paper
DOI: 10.1039/C8NJ04867C
Citation: New J. Chem., 2018,42, 19720-19728
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    Chemoselective phosphine-catalyzed cyanoacylation of α-dicarbonyl compounds: a general method for the synthesis of cyanohydrin esters with one quaternary stereocenter

    H. Zhang, R. Liu, J. Liu, B. Fan, R. Li, Y. Qiao and R. Zhou, New J. Chem., 2018, 42, 19720
    DOI: 10.1039/C8NJ04867C

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