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Synfacts 2008(10): 1077-1077  
DOI: 10.1055/s-2008-1078238
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart ˙ New York

Aluminum-Catalyzed Addition of Phosphites to Aldehydes and Aldimines

Contributor(s): Mark Lautens, Praew Thansandote
J. P. Abell, H. Yamamoto*
The University of Chicago, USA
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Publication History

Publication Date:
22 September 2008 (online)

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Significance

A catalytic and highly selective Al-catalyzed Pudovik reaction has been developed for aldehydes and aldimines to generate α-hydroxy- and α-aminophosphonates in excellent yields and enantioselectivities. Low catalyst loadings (0.5 mol%) can be used and the reaction times are short. The phosphonate and amino moieties of these products can be deprotected together or selectively.