Unusual directive effects in the hydroboration of. beta.,. beta.-disubstituted enamines. Conversion of. alpha.-substituted aldehydes to the corresponding alkenes and. …

B Singaram, CT Goralski, GB Fisher

Index: Singaram, Bakthan; Goralski, Christian T.; Fisher, Gary B. Journal of Organic Chemistry, 1991 , vol. 56, # 19 p. 5691 - 5696

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Citation Number: 38

Abstract

A comprehensive study of the conversion of@,@-disubstituted enamines into the corresponding alkenes and@-amino alcohols by hydroboration-elimination and hydroboration-oxidation, respectively, has been carried out. The amine moiety of &&disubstituted enamines was found to exert a decisive influence on the regioselectivity of the hydroboration reaction involving borane methyl sulfide (BMS). Thus, in the ...