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Diastereoselective Synthesis of β‐Amino‐α‐(trifluoromethyl) Alcohols from Homochiral α‐Dibenzylamino Aldehydes
Author(s) -
Andrés José M.,
Pedrosa Rafael,
PérezEncabo Alfonso
Publication year - 2004
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.200300659
Subject(s) - trifluoromethylation , chemistry , trifluoromethyl , diastereomer , swern oxidation , sodium borohydride , organic chemistry , aldehyde , silane , medicinal chemistry , catalysis , alkyl , dimethyl sulfoxide
Abstract Homochiral α‐dibenzylamino aldehydes, prepared from the corresponding α‐amino acids, react with trimethyl(trifluoromethyl)silane in THF at 0 °C to afford, in good yields and dr , β‐amino‐α‐(trifluoromethyl) alcohols; anti diastereomers were formed as major products in the trifluoromethylation reaction whereas syn diastereomers were obtained as single isomers in a two‐step procedure. Swern oxidation of the mixtures formed in the trifluoromethylation leads to the corresponding α‐dibenzylamino trifluoromethyl ketones which undergo diastereoselective reduction with sodium borohydride. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004)