Highly enantio-and diastereoselective boron aldol reactions of α-heterosubstituted thioacetates with aldehydes and silyl imines

C Gennari, A Vulpetti, G Pain

Index: Gennari, Cesare; Vulpetti, Anna; Pain, Gilles Tetrahedron, 1997 , vol. 53, # 16 p. 5909 - 5924

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Citation Number: 48

Abstract

Boron enolates derived from α-heterosubstituted thioacetates and bearing menthone- derived chiral ligands react with aldehydes to give anti aldols with excellent diastero-and enantiocontrol. Boron enolates derived from tert-butyl α-halothioacetate and bearing menthone-derived chiral ligands react with imines with excellent diastero-and enantiocontrol to give syn α-halo-β-aminothioesters, which can be converted to the corresponding ...