Enzymes in organic chemistry .5. First and chemo-enzymatic synthesis of alpha-aminooxyphosphonic acids of high enantiomeric excess

被引:26
作者
Drescher, M [1 ]
Hammerschmidt, F [1 ]
机构
[1] UNIV VIENNA,INST ORGAN CHEM,A-1090 VIENNA,AUSTRIA
关键词
ENANTIOSELECTIVE HYDROLYSIS; ABSOLUTE-CONFIGURATION; ASYMMETRIC-SYNTHESIS; PHENYLALANINE; ANALOGS; PHOSPHONATES; DERIVATIVES; INHIBITORS; REDUCTION; ESTERS;
D O I
10.1016/S0040-4020(97)00174-9
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
alpha-Acyloxyphosphonates (+/-)-5a and (+/-)-5b, derived from 3-phenylpropionaldehyde and acetaldehyde. were involved by lipase-catalyzed enantioselective hydrolysis. Three of the four chiral, non-racemic alpha-hydroxyphosphonates obtained had 99% ee. the fourth 91%. They were transformed chemically into alpha-aminooxyphosphonic acids. (C) 1997 Elsevier Science Ltd.
引用
收藏
页码:4627 / 4636
页数:10
相关论文
共 23 条
[1]   Catalytic asymmetric synthesis of alpha-hydroxy phosphonates using the Al-Li-BINOL complex [J].
Arai, T ;
Bougauchi, M ;
Sasai, H ;
Shibasaki, M .
JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (09) :2926-2927
[2]   ACCURATE IN-SITU P-31(H-1) ASSAY OF ENANTIOPURITY IN ALPHA-HYDROXYPHOSPHONATE ESTERS USING A DIAZAPHOSPHOLIDINE DERIVATIZING AGENT-ZETA [J].
DEVITT, PG ;
MITCHELL, MC ;
WEETMAN, JM ;
TAYLOR, RJ ;
KEE, TP .
TETRAHEDRON-ASYMMETRY, 1995, 6 (08) :2039-2044
[3]   OPTICALLY-ACTIVE 1-AMINOALKYLPHOSPHONIC ACIDS [J].
DHAWAN, B ;
REDMORE, D .
PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, 1987, 32 (3-4) :119-144
[4]   DIETHOXYMETHYLPHOSPHONITES AND PHOSPHINATES - INTERMEDIATES FOR THE SYNTHESIS OF ALPHA-BETA-AMINOALKYLPHOSPHONOUS AND GAMMA-AMINOALKYLPHOSPHONOUS ACIDS [J].
DINGWALL, JG ;
EHRENFREUND, J ;
HALL, RG .
TETRAHEDRON, 1989, 45 (12) :3787-3808
[5]  
DRESCHER M, 1995, SYNTHESIS-STUTTGART, P1267
[6]   ENZYMES IN ORGANIC-CHEMISTRY .2. LIPASE-CATALYZED HYDROLYSIS OF 1-ACYLOXY-2-ARYLETHYLPHOSPHONATES AND SYNTHESIS OF PHOSPHONIC ACID ANALOGS OF L-PHENYLALANINE AND L-TYROSINE [J].
DRESCHER, M ;
LI, YF ;
HAMMERSCHMIDT, F .
TETRAHEDRON, 1995, 51 (17) :4933-4946
[7]  
Eidenhammer G, 1996, SYNTHESIS-STUTTGART, P748
[8]   ENANTIOSELECTIVE SYNTHESIS OF DIETHYL 1-HYDROXYALKYLPHOSPHONATES VIA OXAZABOROLIDINE CATALYZED BORANE REDUCTION OF DIETHYL ALPHA-KETOPHOSPHONATES [J].
GAJDA, T .
TETRAHEDRON-ASYMMETRY, 1994, 5 (10) :1965-1972
[9]   DETERMINATION OF ABSOLUTE-CONFIGURATION OF ALPHA-HYDROXYPHOSPHONATES BY P-31 NMR-SPECTROSCOPY OF CORRESPONDING MOSHER ESTERS [J].
HAMMERSCHMIDT, F ;
LI, YF .
TETRAHEDRON, 1994, 50 (34) :10253-10264
[10]  
Hughes D.L., 1992, ORG REACT, V42, P335, DOI [DOI 10.1002/0471264180.0R042.02, 10.1002/chin.200331284, DOI 10.1002/CHIN.200331284]