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Issue 8, 2014
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Organocatalytic enantioselective hydrophosphonylation of aldehydes

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Abstract

We report our results concerning the first squaramide-catalysed hydrophosphonylation of aldehydes. In all cases, the reactions proceeded smoothly and cleanly under mild reaction conditions rendering final α-hydroxy phosphonates in very good yields and high enantioselectivities. It is one of the few organocatalytic examples of this reaction using aldehydes. It is the first time that diphenylphosphite (1e) has been successfully employed in a chiral Pudovik reaction with aldehydes, in contrast to the dialkylphosphites used in previously published procedures, extending the generality of this asymmetric methodology.

Graphical abstract: Organocatalytic enantioselective hydrophosphonylation of aldehydes

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Publication details

The article was received on 02 Dec 2013, accepted on 18 Dec 2013 and first published on 18 Dec 2013


Article type: Paper
DOI: 10.1039/C3OB42403K
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Org. Biomol. Chem., 2014,12, 1258-1264

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    Organocatalytic enantioselective hydrophosphonylation of aldehydes

    J. V. Alegre-Requena, E. Marqués-López, P. J. Sanz Miguel and R. P. Herrera, Org. Biomol. Chem., 2014, 12, 1258
    DOI: 10.1039/C3OB42403K

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