MICROBIOLOGICAL SYNTHESIS OF OPTICALLY-ACTIVE (2R,3S)-2,3-DEUTERIO-CYCLOHEXAN-1-ONES AND (2R,3S)-2-METHYL-3-DEUTERIOCYCLOHEXAN-1-ONE - ENANTIOSPECIFIC ANTI-ADDITION OF HYDROGEN TO THE DOUBLE-BOND OF CYCLOHEX-2-EN-1-ONES

被引:6
作者
DAUPHIN, G
GOURCY, JG
VESCHAMBRE, H
机构
[1] Laboratoire de Chimie Organique Biologique, URA 485 du CNRS
关键词
D O I
10.1016/S0957-4166(00)82289-2
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
Addition of hydrogen to the double bond of cyclohexenones during microbiological reduction by Beauveria sulfurescens gives the trans product in high yield (90%) resulting from anti-addition to the si face on C-2 and the re face on C-3.
引用
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页码:595 / 598
页数:4
相关论文
共 11 条
[1]  
BARRY J, 1970, B SOC CHIM FR, P989
[2]   A MECHANISTIC STUDY OF THE RHODIUM-CATALYZED CYCLIZATION OF 4-HEXENALS - REACTIONS OF DEUTERIO-4-HEXENALS [J].
CAMPBELL, RE ;
LOCHOW, CF ;
VORA, KP ;
MILLER, RG .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1980, 102 (18) :5824-5830
[3]   MICROBIOLOGICAL SYNTHESIS AND CIRCULAR-DICHROISM OF OPTICALLY-ACTIVE 2-DEUTERIO-CYCLOALKANONES [J].
DAUPHIN, G ;
GRAMAIN, JC ;
KERGOMARD, A ;
RENARD, MF ;
VESCHAMBRE, H .
TETRAHEDRON LETTERS, 1980, 21 (44) :4275-4278
[4]   MICROBIOLOGICAL SYNTHESIS OF OPTICALLY-ACTIVE 3-DEUTERIO-CYCLOALKANONES [J].
DAUPHIN, G ;
GRAMAIN, JC ;
KERGOMARD, A ;
RENARD, MF ;
VESCHAMBRE, H .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1980, (07) :318-319
[5]  
DJERASSI C, 1978, TETRAHEDRON LETT, P535
[6]   INDUCIBILITY OF AN ENONE REDUCTASE SYSTEM IN THE FUNGUS BEAUVERIA-SULFURESCENS - APPLICATION IN ENANTIOSELECTIVE ORGANIC-SYNTHESIS [J].
FAUVE, A ;
RENARD, MF ;
VESCHAMBRE, H .
JOURNAL OF ORGANIC CHEMISTRY, 1987, 52 (22) :4893-4897
[7]  
GANNON WF, 1960, ORG SYNTH, V40, P14
[8]  
GUACIARO MA, 1978, TETRAHEDRON LETT, P4661
[9]  
KERGOMARD A, 1978, TETRAHEDRON LETT, V52, P5197
[10]   PI-ELECTRON STERIC EFFECTS ON CONFORMATIONAL EQUILIBRIA [J].
LAMBERT, JB ;
CLIKEMAN, RR .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1976, 98 (14) :4203-4211