Diastereoselective Synthesis of β-Amino-α-(trifluoromethyl) Alcohols from Homochiral α-Dibenzylamino Aldehydes

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 reactio...

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Veröffentlicht in:	European journal of organic chemistry 2004-04, Vol.2004 (7), p.1558-1566
Hauptverfasser:	Andrés, José M., Pedrosa, Rafael, Pérez-Encabo, Alfonso
Format:	Artikel
Sprache:	eng
Schlagworte:	Alcohols Amino aldehydes Asymmetric Synthesis Fluorine Trifluoromethylation
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container_title	European journal of organic chemistry
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creator	Andrés, José M. Pedrosa, Rafael Pérez-Encabo, Alfonso
description	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)
doi_str_mv	10.1002/ejoc.200300659
format	Article
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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)</description><identifier>ISSN: 1434-193X</identifier><identifier>EISSN: 1099-0690</identifier><identifier>DOI: 10.1002/ejoc.200300659</identifier><language>eng</language><publisher>Weinheim: WILEY-VCH Verlag</publisher><subject>Alcohols ; Amino aldehydes ; Asymmetric Synthesis ; Fluorine ; Trifluoromethylation</subject><ispartof>European journal of organic chemistry, 2004-04, Vol.2004 (7), p.1558-1566</ispartof><rights>Copyright © 2004 WILEY‐VCH Verlag GmbH & Co. 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J. Org. Chem</addtitle><description>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. 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subjects	Alcohols Amino aldehydes Asymmetric Synthesis Fluorine Trifluoromethylation
title	Diastereoselective Synthesis of β-Amino-α-(trifluoromethyl) Alcohols from Homochiral α-Dibenzylamino Aldehydes
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