SYNTHESIS OF OPTICALLY PURE (R)-ALPHA-TRIFLUOROMETHYL-ALANINE AND (S)-ALPHA-TRIFLUOROMETHYL-ALANINE

被引:74
作者
BRAVO, P [1 ]
CAPELLI, S [1 ]
MEILLE, SV [1 ]
VIANI, F [1 ]
ZANDA, M [1 ]
KUKHAR, VP [1 ]
SOLOSHONOK, VA [1 ]
机构
[1] UKRAINIAN ACAD SCI,INST BIOORGAN CHEM & PETROCHEM,KIEV 252660,UKRAINE
关键词
D O I
10.1016/S0957-4166(00)86276-X
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
(+)-(R)- and (-)-(S)-3,3,3-trifluoro-2-methyl-alanine (1) were synthesized from (+)-(R)-methyl-p-tolylsulphoxide (5) and N-alkoxycarbonylimino derivatives 4 of methyl 3,3,3-trifluoropyruvate (3). The absolute configuration was determined by X-ray analyses of two synthetic intermediates (2S,R(S))-6a and (2R,R(S))-6c.
引用
收藏
页码:2009 / 2018
页数:10
相关论文
共 36 条
[1]   COMPLETION AND REFINEMENT OF CRYSTAL-STRUCTURES WITH SIR92 [J].
ALTOMARE, A ;
CASCARANO, G ;
GIACOVAZZO, C ;
GUAGLIARDI, A .
JOURNAL OF APPLIED CRYSTALLOGRAPHY, 1993, 26 (pt 3) :343-350
[2]   SYNTHESIS OF REACTIVITY OF LAMBDA-5-PHOSPHAZENES - USES AS SYNTHETIC INTERMEDIATES [J].
BARLUENGA, J ;
PALACIOS, F .
ORGANIC PREPARATIONS AND PROCEDURES INTERNATIONAL, 1991, 23 (01) :1-65
[3]  
BOSH R, 1982, TETRAHEDRON, V38, P3579
[4]   OPTICALLY PURE AND FLUOROSUBSTITUTED ACYCLOVIR ANALOGS [J].
BRAVO, P ;
RESNATI, G ;
VIANI, F .
TETRAHEDRON, 1993, 49 (03) :713-720
[5]   SYNTHESIS AND PHARMACOLOGICAL EVALUATION OF ENANTIOMERICALLY PURE 4-DEOXY-4-FLUOROMUSCARINES [J].
BRAVO, P ;
RESNATI, G ;
ANGELI, P ;
FRIGERIO, M ;
VIANI, F ;
ARNONE, A ;
MARUCCI, G ;
CANTALAMESSA, F .
JOURNAL OF MEDICINAL CHEMISTRY, 1992, 35 (17) :3102-3110
[6]   ASYMMETRIC-SYNTHESIS AND STRUCTURAL-ANALYSIS OF 5-O-BENZOYL-2,3-DIDEOXY-3-FLUORO-ALPHA,BETA-D-RIBOFURANOSE AND 5-O-BENZOYL-2,3-DIDEOXY-3-FLUORO-ALPHA,BETA-D-XYLOFURANOSE FROM HOMOCHIRAL 1-FLUORO-3-SULFINYLACETONE [J].
BRAVO, P ;
PIOVOSI, E ;
RESNATI, G ;
FRONZA, G .
JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (21) :5171-5176
[7]  
BRAVO P, 1994, IN PRESS TETRAHEDRON
[8]  
BURGER K, 1990, CHEM ZTG, V114, P101
[9]   3,3,3-TRIFLUORO-2-ISOCYANOPROPIONATES, NEW VERSATILE BUILDING-BLOCKS FOR THE INTRODUCTION OF TRIFLUOROMETHYL GROUPS INTO ORGANIC-MOLECULES [J].
BURGER, K ;
SCHIERLINGER, C ;
MUTZE, K .
JOURNAL OF FLUORINE CHEMISTRY, 1993, 65 (1-2) :149-152
[10]  
CHRISTENSEN HN, 1963, BIOCHIM BIOPHYS ACTA, V74, P385