Tetrahedron: Asymmetry

Enantio and diastereoselectivity of cyclohexanone monooxygenase catalyzed oxidation of 1, 3-dithioacetals

S Colonna, N Gaggero, G Carrea, P Pasta

Index: Colonna, Stefano; Gaggero, Nicoletta; Carrea, Giacomo; Pasta, Piero Tetrahedron Asymmetry, 1996 ,  vol. 7,  # 2  p. 565 - 570

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Citation Number: 30

Abstract

The asymmetric oxidation of 2-substituted dithianes, dithiolanes and oxathiolanes catalyzed by cyclohexanone monooxygenase (CMO) has been examined. The introduction of substituents at the C-2 causes a decrease of the ee with the exception of 2-benzoyl-1, 3- dithiane monosulfoxide (90% ee). With 2-monosubstituted dithioacetals CMO yields preferentially or exclusively the trans diastereoisomer. The binding of the 1, 3- ...