The Journal of Organic Chemistry

A selectivity study of activated ketal reduction with borane dimethyl sulfide

B Bartels, R Hunter

Index: Bartels, Birgit; Hunter, Roger Journal of Organic Chemistry, 1993 , vol. 58, # 24 p. 6756 - 6765

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Citation Number: 29

Abstract

A chemo-and regioselectivity study of the reagent combination BHrSMedTMSOTf for ketal reduction has been undertaken. It has revealed that simple l, &dioxanes reduce cleanly at low temperature in CHzCl2 while simple 1, 3-dioxolanes may give complete ring cleavage and dimerization products. A study of reduction of 4-substituted 1, 3-dioxolanes has revealed a solvent-directed regioselectivity which in THF favors the secondary protected ...

~38%

~58%

~24%

~37%

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