On the baker's yeast mediated transformation of α-bromoenones.: Synthesis of (1S,2R)-2-bromoindan-1-ol and (2S,3S)-3-bromo-4-phenylbutan-2-ol

被引：25

作者：

Aleu, J ^{[1
]}

Fronza, G ^{[1
]}

Fuganti, C ^{[1
]}

Perozzo, V ^{[1
]}

Serra, S ^{[1
]}

机构：

[1] Politecn Milan, Dipartimento Chim, Ctr Studio Sostanze Organiche Naturali, I-20131 Milan, Italy

来源：

TETRAHEDRON-ASYMMETRY | 1998年 / 9卷 / 09期

关键词：

D O I：

10.1016/S0957-4166(98)00128-1

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

Fermenting baker's yeast converts alpha-bromo substituted enones 7 and 10 into enantiomerically pure (1S,2R)2-bromoindan-1-ol 3 and (2S,3S)-3-bromo-4-phenylbutan-2-ol 11, respectively, through the intermediacy of the corresponding saturated ketones. Structurally related 16 provides the (2R)-allylic alcohol 17 prevalently. (C) 1998 Elsevier Science Ltd. All rights reserved.

引用

页码：1589 / 1596

页数：8

共 22 条

[1]

BOYD DR, 1996, TETRAHEDRON-ASYMMETR, V7, P59

[2]

CLARK W, 1997, BIOTRANS 97, P1

[3] alpha,beta-Unsaturated aminoketones. III. alpha- and beta-Morpholinobenzalacetones [J].

Cromwell, NH .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1940, 62 :3470-3473

[4] CHEMOENZYMATIC SYNTHESIS OF 1,2-AMINO-ALCOHOLS AND 1,3-AMINO-ALCOHOLS AND THEIR USE IN THE ENANTIOSELECTIVE REDUCTION OF ACETOPHENONE AND ANTI-ACETOPHENONE OXIME METHYL-ETHER WITH BORANE [J].

DIDIER, E ;

LOUBINOUX, B ;

TOMBO, GMR ;

RIHS, G .

TETRAHEDRON, 1991, 47 (27) :4941-4958

[5] BAKERS-YEAST REDUCTION OF ARYLIDENECYCLOALKANONES [J].

FOGLIATO, G ;

FRONZA, G ;

FUGANTI, C ;

LANATI, S ;

RALLO, R ;

RIGONI, R ;

SERVI, S .

TETRAHEDRON, 1995, 51 (37) :10231-10240

[6] STEREOCHEMISTRY OF THE BAKERS-YEAST MEDIATED REDUCTION OF THE C=C BOND OF (Z)-5-BENZOYLOXYHEX-3-EN-2-ONE AND (E)-5-BENZOYLOXYHEX-3-EN-2-ONE [J].

FRONZA, G ;

FUGANTI, C ;

GRASSELLI, P ;

LANATI, S ;

RALLO, R ;

TCHILIBON, S .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1994, (20) :2927-2930

[7] Microbially-aided preparation of (S)-2-methoxycyclohexanone key intermediate in the synthesis of sanfetrinem [J].

Fuganti, C ;

Grasselli, P ;

Mendozza, M ;

Servi, S ;

Zucchi, G .

TETRAHEDRON, 1997, 53 (07) :2617-2624

[8]

FUGANTI C, 1996, J AGR FOOD CHEM, V45, P3616

[9]

Ghosh AK, 1997, SYNTHESIS-STUTTGART, P541, DOI 10.1055/s-1997-1235

[10] PERHYDROINDAN DERIVATIVES .18. USE OF INDENONE KETALS AS DIENOPHILES [J].

HOUSE, HO ;

MCDANIEL, WC .

JOURNAL OF ORGANIC CHEMISTRY, 1977, 42 (12) :2155-2160

← 1 2 3 →