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Organocatalyzed Synthesis of Tertiary α‐Hydroxyphosphonates by a Highly Regioselective Modified Pudovik Reaction
Author(s) -
Barros Maria Teresa,
Phillips Ana Maria Faísca
Publication year - 2011
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201100308
Subject(s) - chemistry , regioselectivity , stereoselectivity , reaction conditions , organic chemistry , stoichiometry , combinatorial chemistry , base (topology) , catalysis , mathematical analysis , mathematics
Abstract An organocatalytic modified Pudovik reaction between dialkyl or diaryl phosphites and α‐haloketones was used to synthesize β‐chloro‐α‐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 β‐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.