Organocatalyzed Synthesis of Tertiary alpha-Hydroxyphosphonates by a Highly Regioselective Modified Pudovik Reaction

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Abstract

An organocatalytic modified Pudovik reaction between dialkyl or diaryl phosphites and alpha-haloketones was used to synthesize beta-chloro-alpha-hydroxyphosphonates in high yields with very high regioselectivity and high stereoselectivity. Aliphatic, aromatic, and cyclic ketones could be used successfully. Under the optimized conditions it was possible to obtain enantiomerically enriched products with a combination of quinine and a stoichiometric racemic base, but the ee values only went up to 40%. The presence of a beta-chloro functionality allows further synthetic elaboration of the hydroxyphosphonates obtained, which could be useful for target-oriented synthesis, as these compounds often have important biological activity.
Original languageUnknown
Pages (from-to)4028-4036
JournalEuropean Journal of Organic Chemistry
Volume2011
Issue number20-21
DOIs
Publication statusPublished - 1 Jan 2011

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