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Asymmetric Addition of Chiral 1,3,2‐Benzoxazaphosphinine 2‐Oxides to Aldehydes: Diastereoselective Synthesis of α‐Substituted β‐Hydroxyphosphonic Acids
Author(s) -
López Beatriz,
Maestro Alicia,
Pedrosa Rafael
Publication year - 2007
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.200601102
Subject(s) - chemistry , enantiopure drug , diastereomer , phosphorus , organic chemistry , medicinal chemistry , chiral auxiliary , stereochemistry , enantioselective synthesis , catalysis
The addition of stabilized phosphorus anions to aldehydes leads to α‐substituted β‐hydroxyphosphonates. The diastereoselectivity of the process is strongly influenced by the substitution of the phosphorus atom. Whereas P ‐ethyl derivatives provide a mixture of three isomers, the presence of a benzyl group enhances the stereocontrol, providing two diastereomers in ratios of up to 5:1. Elimination of the aminomenthol appendage produces enantiopure α‐phenyl‐β‐hydroxyphosphonic acids in high yields.(© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007)