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Synfacts 2006(12): 1282-1282
DOI: 10.1055/s-2006-949503
DOI: 10.1055/s-2006-949503
Organo- and Biocatalysis
© Georg Thieme Verlag Stuttgart · New York
l-Prolinamide-Catalyzed Enantioselective Synthesis of α-Hydroxyphosphonates
R. Dodda, C.-G. Zhao*
University of Texas at San Antonio, USA
Further Information
Publication History
Publication Date:
22 November 2006 (online)
![](https://www.thieme-connect.de/media/synfacts/200612/lookinside/thumbnails/10.1055-s-2006-949503-1.jpg)
Significance
The first organocatalytic cross aldol reaction of ketones with diethyl formylphosphonate hydrate is reported. In the presence of readily available l-prolinamide as catalyst, secondary α-hydroxyphosphonates have been synthesized in moderate to good yields (up to 95%), good diastereoselectivity (up to 95:5) and high enantiomeric ratios (up to >99:1). Besides acetone, other unsubstituted aliphatic ketones also participate in this reaction, however with a lower reactivity. Substituted or cyclic ketones may also be used for this cross aldol reaction.