ON THE MODE OF BAKERS-YEAST REDUCTION OF BENZYLIDENECYCLOHEXANONE

被引：15

作者：

FRONZA, G ^{[1
]}

FOGLIATO, G ^{[1
]}

FUGANTI, C ^{[1
]}

LANATI, S ^{[1
]}

RALLO, R ^{[1
]}

SERVI, S ^{[1
]}

机构：

[1] CNR,CTR STUDIO SOSTANZE ORGAN NAT,POLITECN MILANO,DIPARTIMENTO CHIM,I-20131 MILAN,ITALY

来源：

TETRAHEDRON LETTERS | 1995年 / 36卷 / 01期

关键词：

BAKERS YEAST; REDUCTION; ENANTIOSELECTIVITY; DIASTEREOSELECTIVITY;

D O I：

10.1016/0040-4039(94)02190-M

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Baker's yeast reduction of benzylidene cyclohexanone 1 affords, as major transformation product, enantiomerically pure (S) carbinol 3, yielding in two steps (2S) 2-acetoxycyclohexanone 6, close to nearly racemic saturated ketone 4, whereas carbinol 5 and its enantiomer 8 can be obtained from 3 upon LiAlH4 reduction upon baker's yeast reduction to 7, followed by inversion of configuration, respectively.

引用

页码：123 / 124

页数：2

共 4 条

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AZERAD, R .

TETRAHEDRON LETTERS, 1994, 35 (19) :3091-3094

[2] ENANTIODIFFERENTIATING FUNCTIONALIZATION OF CIS-CYCLOALKANE-1,2-DIOLS AND CIS-ENDO-5-NORBORNEN-2,3-YLENEBIS(METHANOL) VIA CHIRAL SPIROACETALS DERIVED FROM L-MENTHONE [J].

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JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (11) :2599-2605

[3] HYDROXY-DIRECTED HYDROALUMINATIONS - A STEREOSELECTIVE APPROACH TO CYCLOALKANOLS FROM BETA-ARYL ENONES [J].

KOCH, K ;

SMITROVICH, JH .

TETRAHEDRON LETTERS, 1994, 35 (08) :1137-1140

[4]

SERVI S, 1990, SYNTHESIS-STUTTGART, P1

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