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

页码：1558 / 1566

页数：9

共 30 条

[1] Stereoselective and enantioselective synthesis of anti-1-(Trifluoromethyl) amino alcohols [J].

Abouabdellah, A ;

Bègué, JP ;

Bonnet-Delpon, D ;

Kornilov, A ;

Rodrigues, I ;

Richard, C .

JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (19) :6529-6534

[2] Stereodivergent synthesis of all diastereomers of 4-aminoheptane-3,5-diol from (L)-serine [J].

Andrés, JM ;

Pedrosa, R .

TETRAHEDRON, 1998, 54 (21) :5607-5616

[3] Synthesis of enantiopure syn-beta-amino alcohols. A simple case of chelation-controlled additions of diethylzinc to alpha-(dibenzylamino) aldehydes [J].

Andres, JM ;

Barrio, R ;

Martinez, MA ;

Pedrosa, R ;

PerezEncabo, A .

JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (13) :4210-4213

[4] Diastereoselective synthesis of enantiopure γ-amino-β-hydroxy acids by Reformatsky reaction of chiral α-dibenzylamino aldehydes [J].

Andrés, JM ;

Pedrosa, R ;

Pérez, A ;

Pérez-Encabo, A .

TETRAHEDRON, 2001, 57 (40) :8521-8530

[5]

Banks R.E., 1994, ORGANOFLUORINE CHEM

[6] STEREOSELECTIVE SYNTHESIS AND INHIBITOR PROPERTIES TOWARDS HUMAN-LEUKOCYTE ELASTASE OF CHIRAL BETA-PEPTIDYL TRIFLUOROMETHYL ALCOHOLS [J].

BEGUE, JP ;

BONNETDELPON, D ;

FISCHERDURAND, N ;

AMOUR, A ;

REBOUDRAVAUX, M .

TETRAHEDRON-ASYMMETRY, 1994, 5 (06) :1099-1110

[7] A VERSATILE SYNTHESIS OF AMINO TRIFLUOROMETHYL KETONES AND ALCOHOLS [J].

BEGUE, JP ;

BONNETDELPON, D ;

SDASSI, H .

TETRAHEDRON LETTERS, 1992, 33 (14) :1879-1882

[8] NONPEPTIDIC INHIBITORS OF HUMAN-LEUKOCYTE ELASTASE .6. DESIGN OF A POTENT, INTRATRACHEALLY ACTIVE, PYRIDONE-BASED TRIFLUOROMETHYL KETONE [J].

BERNSTEIN, PR ;

GOMES, BC ;

KOSMIDER, BJ ;

VACEK, EP ;

WILLIAMS, JC .

JOURNAL OF MEDICINAL CHEMISTRY, 1995, 38 (01) :212-215

[9] SYNTHESIS AND REDUCTION OF ALPHA-AMINO KETONES DERIVED FROM LEUCINE [J].

DUFOUR, MN ;

JOUIN, P ;

PONCET, J ;

PANTALONI, A ;

CASTRO, B .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1986, (11) :1895-1899

[10] A METHOD FOR THE STEREOSELECTIVE SYNTHESIS OF PEPTIDYL TRIFLUOROMETHYL KETONES [J].

EDWARDS, PD .

TETRAHEDRON LETTERS, 1992, 33 (30) :4279-4282

← 1 2 3 →