Asymmetric hydrogenation of beta-ketophosphonates and beta-ketothiophosphonates with chiral Ru(II) catalysts

被引:40
作者
Gautier, I [1 ]
RatovelomananaVidal, V [1 ]
Savignac, P [1 ]
Genet, JP [1 ]
机构
[1] ECOLE POLYTECH,DCPH,CNRS,LAB HETEROELEMENTS & COORDINAT,F-91128 PALAISEAU,FRANCE
关键词
D O I
10.1016/0040-4039(96)01733-9
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Asymmetric hydrogenation of beta-ketophosphonates and beta-ketothiophosphonates is described. Enantiomeric excesses up to 99% were obtained. Copyright (C) 1996 Elsevier Science Ltd
引用
收藏
页码:7721 / 7724
页数:4
相关论文
共 31 条
[1]   SYNTHESIS OF (1S,2S)-PHOSPHOTHREONINE VIA N-TRIMETHYLSILYLIMINE OF (S)-LACTIC ALDEHYDE [J].
BONGINI, A ;
CAMERINI, R ;
HOFMAN, S ;
PANUNZIO, M .
TETRAHEDRON LETTERS, 1994, 35 (43) :8045-8048
[2]   ALPHA-METHOXY-ALPHA-TRIFLUOROMETHYLPHENYLACETIC ACID, A VERSATILE REAGENT FOR DETERMINATION OF ENANTIOMERIC COMPOSITION OF ALCOHOLS AND AMINES [J].
DALE, JA ;
DULL, DL ;
MOSHER, HS .
JOURNAL OF ORGANIC CHEMISTRY, 1969, 34 (09) :2543-&
[3]   NUCLEAR MAGNETIC-RESONANCE ENANTIOMER REAGENTS - CONFIGURATIONAL CORRELATIONS VIA NUCLEAR MAGNETIC-RESONANCE CHEMICAL-SHIFTS OF DIASTEREOMERIC MANDELATE, O-METHYLMANDELATE, AND ALPHA-METHOXY-ALPHA-TRIFLUOROMETHYLPHENYLACETATE (MTPA) ESTERS [J].
DALE, JA ;
MOSHER, HS .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1973, 95 (02) :512-519
[4]   OPTICALLY-ACTIVE 1-AMINOALKYLPHOSPHONIC ACIDS [J].
DHAWAN, B ;
REDMORE, D .
PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, 1987, 32 (3-4) :119-144
[5]   THE PREPARATION AND PROPERTIES OF PHOSPHONIC ACIDS [J].
FREEDMAN, LD ;
DOAK, GO .
CHEMICAL REVIEWS, 1957, 57 (03) :479-523
[6]  
GENET JP, 1995, TETRAHEDRON LETT, V36, P4801
[7]   ENANTIOSELECTIVE HYDROGENATION REACTIONS WITH A FULL SET OF PREFORMED AND PREPARED IN-SITU CHIRAL DIPHOSPHINE-RUTHENIUM(II) CATALYSTS [J].
GENET, JP ;
PINEL, C ;
RATOVELOMANANAVIDAL, V ;
MALLART, S ;
PFISTER, X ;
BISCHOFF, L ;
DEANDRADE, MCC ;
DARSES, S ;
GALOPIN, C ;
LAFFITTE, JA .
TETRAHEDRON-ASYMMETRY, 1994, 5 (04) :675-690
[8]   NOVEL, GENERAL-SYNTHESIS OF THE CHIRAL CATALYSTS DIPHOSPHINE-RUTHENIUM(II) DIALLYL COMPLEXES AND A NEW PRACTICAL IN-SITU PREPARATION OF CHIRAL RUTHENIUM(II) CATALYSTS [J].
GENET, JP ;
PINEL, C ;
RATOVELOMANANAVIDAL, V ;
MALLART, S ;
PFISTER, X ;
DEANDRADE, MCC ;
LAFFITTE, JA .
TETRAHEDRON-ASYMMETRY, 1994, 5 (04) :665-674
[9]   A NEW ENANTIOSELECTIVE SYNTHESIS OF GLYCIDATES VIA DYNAMIC KINETIC RESOLUTION OF RACEMIC 2-CHLORO-3-KETO ESTERS USING CHIRAL RU(II) COMPLEXES [J].
GENET, JP ;
DEANDRADE, MCC ;
RATOVELOMANANAVIDAL, V .
TETRAHEDRON LETTERS, 1995, 36 (12) :2063-2066
[10]  
GENET JP, 1996, IN PRESS ACS