Asymmetric Synthesis of O??Protected Acyloins Using Enoate Reductases: Stereochemical Control through Protecting Group Modification

…, C Stueckler, NJ Mueller, D Pressnitz…

Index: Winkler, Christoph K.; Stueckler, Clemens; Mueller, Nicole J.; Pressnitz, Desiree; Faber, Kurt European Journal of Organic Chemistry, 2010 , # 33 p. 6354 - 6358

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Citation Number: 12

Abstract

Abstract O-Protected cyclic acyloins were obtained in nonracemic form through asymmetric bioreduction of α, β-unsaturated alkoxy ketones by using 11 different enoate reductases from the “Old Yellow Enzyme” family. The stereochemical outcome of the biotransformation could be switched by variation of the O-protecting group or by the ring size of the substrate, which allows access to both stereoisomers in up to> 97% ee Whereas α-alkoxy enones ...