The mode of bakers' yeast transformation of 3-chloropropiophenone and related ketones. Synthesis of (2S)-[2-2H] propiophenone,(R)-fluoxetine, and (R)-and (S)- …

G Fronza, C Fuganti, P Grasselli…

Index: Fronza; Fuganti; Grasselli; Mele Journal of Organic Chemistry, 1991 , vol. 56, # 21 p. 6019 - 6023

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Citation Number: 55

Abstract

Yeast treatment of 3-chloropropiophenone (2) affords the expected (1S)-3-chloro-l- phenylpropan-l-ol (3) as well as ca. 30% of propiophenone (5). The conversion of 2 into 5 is accompanied by formal elimination of hydrochloric acid, followed by yeast saturation of the double bond of the intermediate phenyl vinyl ketone (4). Monodeuteriopropiophenone formed via yeast treatment from a, a-dideuterio-3-chloropropiophenone (8) was shown to ...