Tetrahedron: Asymmetry

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

J Aleu, G Fronza, C Fuganti, V Perozzo, S Serra

Index: Aleu, Josephina; Fronza, Giovanni; Fuganti, Claudio; Perozzo, Valentina; Serra, Stefano Tetrahedron Asymmetry, 1998 , vol. 9, # 9 p. 1589 - 1596

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Citation Number: 23

Abstract

Fermenting baker's yeast converts α-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.