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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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Article information


Submitted
02 Dec 2013
Accepted
18 Dec 2013
First published
18 Dec 2013

Org. Biomol. Chem., 2014,12, 1258-1264
Article type
Paper
Author version available

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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