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Preparation of chiral trans-5-substituted-acenaphthene-1,2-diols by baker's yeast-mediated reduction of 5-substituted-acenaphthylene-1,2-diones

Release Time:2019-03-09  Hits:

Indexed by: Journal Article

Date of Publication: 2010-04-21

Journal: TETRAHEDRON-ASYMMETRY

Included Journals: SCIE

Volume: 21

Issue: 7

Page Number: 825-830

ISSN: 0957-4166

Abstract: A series of trans-5-substauted-acenaphthene-1,2-diols were obtained in 21-72% yield with 97-100% ee by baker's yeast-mediated reduction of the corresponding acenaphthylene-1,2-diones, in the presence of DMSO as a co-solvent and under vigorous agitation The absolute configuration of (-)-trans-5-methoxy-acenaphthene-1,2-diol trans-3b and (-)-trans-5-bromo-acenaphthene-12-diol trans-3c was assigned as (S,S) and (-)-trans-5-thiomorpholin-acenaphthene-1,2-diol trans-3d was established as (R,R) by exciton-coupled circular dichroism. (C) 2010 Elsevier Ltd All rights reserved

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