Baker's yeast reduction of α-alkyl-α-hydroxy-β-keto esters

被引:17
作者
Buisson, D
Baucherel, X
Levoirier, E
Juge, S
机构
[1] Univ Paris 05, CNRS, UMR 8601,Grp Metab & Biosynthese, Chim & Biochim Pharmacol & Toxicol Lab, F-75270 Paris 06, France
[2] Univ Cergy Pontoise, Unite Mixte Synthese Organ Select & Chim Organome, ESCOM, CNRS,EP 1822, F-95031 Cergy Pontoise, France
关键词
microbial reactions; resolution; hydroxy eaters; diols;
D O I
10.1016/S0040-4039(99)02274-1
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Cyclic or acyclic alpha-alkyl-alpha-hydroxy-beta-keto esters were reduced by baker's yeast with high stereospecificity. In the former case, one enantiomer of the racemic mixture was transformed into optically active trans-dihydroxy compounds, while the remaining alpha-hydroxy-beta-keto ester was enantiopure. (C) 2000 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:1389 / 1392
页数:4
相关论文
共 26 条
[1]   Selective synthesis of 1-, and 3-carbomethoxy 2-tetralol stereoisomers by microbial reduction of the corresponding tetralones [J].
Abalain, C ;
Buisson, D ;
Azerad, R .
TETRAHEDRON-ASYMMETRY, 1996, 7 (10) :2983-2996
[2]  
AKITA H, 1993, SYNTHESIS-STUTTGART, P513
[3]   Monohydroxylation of cyclic and acyclic β-keto esters with molecular oxygen catalyzed by cobalt(II) chloride in neutral conditions [J].
Baucherel, X ;
Levoirier, E ;
Uziel, J ;
Juge, S .
TETRAHEDRON LETTERS, 2000, 41 (09) :1385-1387
[4]   AN OXIDATIVE REARRANGEMENT OF TERT-BUTYL (3RS,5SR)-2-ETHOXYCARBONYLCARBAPEN-1-EM-3-CARBOXYLATE TO TERT-BUTYL (1RS,5SR,7RS,8SR)-8-ETHOXYCARBONYL-8-HYDROXY-3-OXO-2-OXA-6-AZABICYCLO[3.3.0]OCTANE-7-CARBOXYLATE [J].
BEAGLEY, B ;
LARSEN, DS ;
PRITCHARD, RG ;
STOODLEY, RJ ;
WHITING, A .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1989, (06) :1127-1137
[5]   A CHEMOENZYMATIC SYNTHESIS OF (+)-CASTANOSPERMINE [J].
BHIDE, R ;
MORTEZAEI, R ;
SCILIMATI, A ;
SIH, CJ .
TETRAHEDRON LETTERS, 1990, 31 (34) :4827-4830
[6]   Preparation and use of (S)-O-acetyllactyl chloride (Mosandl's reagent) as a chiral derivatizing agent [J].
Buisson, D ;
Azerad, R .
TETRAHEDRON-ASYMMETRY, 1999, 10 (15) :2997-3002
[7]   MICROBIAL REDUCTION OF 1-TETRALONE 2-CARBOXYESTERS AS A SOURCE OF NEW ASYMMETRIC SYNTHONS [J].
BUISSON, D ;
CECCHI, R ;
LAFFITTE, JA ;
GUZZI, U ;
AZERAD, R .
TETRAHEDRON LETTERS, 1994, 35 (19) :3091-3094
[8]   MICROBIAL REDUCTION OF 2-CHLORO-3-ARYL-3-OXOPROPIONIC ACID-ESTERS [J].
CABON, O ;
LARCHEVEQUE, M ;
BUISSON, D ;
AZERAD, R .
TETRAHEDRON LETTERS, 1992, 33 (48) :7337-7340
[9]   THE MICROBIAL REDUCTION OF 2-CHLORO-3-OXOESTERS [J].
CABON, O ;
BUISSON, D ;
LARCHEVEQUE, M ;
AZERAD, R .
TETRAHEDRON-ASYMMETRY, 1995, 6 (09) :2199-2210
[10]   BAKERS-YEAST REDUCTIONS OF BETA-OXOPYRROLIDINECARBOXYLATES - SYNTHESIS OF (+)-CIS-(2R,3S)-3-HYDROXYPROLINE AND (-)-(1S,5S)-GEISSMAN-WAISS LACTONE, A USEFUL PRECURSOR TO PYRROLIZIDINE ALKALOIDS [J].
COOPER, J ;
GALLAGHER, PT ;
KNIGHT, DW .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1993, (12) :1313-1317