Diastereoselective synthesis of β-amino-α-(trifluoromethyl) alcohols from homochiral α-dibenzylamino aldehydes

被引：16
作者：
Andrés, JM [1 ]
Pedrosa, R [1 ]
Pérez-Encabo, A [1 ]
机构：
[1] Univ Valladolid, Fac Ciencias, Dept Quim Organ, E-47011 Valladolid, Spain
来源：
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2004年 / 2004卷 / 07期
关键词：
alcohols; amino aldehydes; asymmetric synthesis; fluorine; trifluoromethylation;
D O I：
10.1002/ejoc.200300659
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Homochiral alpha-dibenzylamino aldehydes, prepared from the corresponding a-amino acids, react with trimethyl(trifluoromethyl)silane in THF at 0 degreesC to afford, in good yields and dr, beta-amino-alpha-(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 alpha-dibenzylamino trifluoromethyl ketones which undergo diastereoselective reduction with sodium borohydride. ((C) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004)
引用
收藏
页码：1558 / 1566
页数：9
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