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Phenylsilane as an effective desulfinylation reagent.

ABSTRACT: The reduction using phenylsilane in a KOH-catalyzed system was applied successfully to the conversion of sulfinyl-substituted cyclopropylcarboxylates into the corresponding alcohols. The presence of sulfinyl substituents in the ?-position to the carboxylate group caused a desulfinylation product formation with full regio- and stereoselectivity, instead of a carbonyl group reduction. Investigations performed on different ?-sulfinylcarbonyl compounds revealed that phenylsilane treatment constitutes a regiospecific method for the desulfinylation of a-sulfinylesters; for corresponding ketones the reaction course depends on the character of the carbonyl group.

SUBMITTER: Midura WH

PROVIDER: S-EPMC5550773 | biostudies-literature | 2017

REPOSITORIES: biostudies-literature

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Phenylsilane as an effective desulfinylation reagent.

Midura Wanda H WH Rzewnicka Aneta A Krysiak Jerzy A JA

Beilstein journal of organic chemistry 20170801

The reduction using phenylsilane in a KOH-catalyzed system was applied successfully to the conversion of sulfinyl-substituted cyclopropylcarboxylates into the corresponding alcohols. The presence of sulfinyl substituents in the α-position to the carboxylate group caused a desulfinylation product formation with full regio- and stereoselectivity, instead of a carbonyl group reduction. Investigations performed on different α-sulfinylcarbonyl compounds revealed that phenylsilane treatment constitute ...[more]

PMID: 28845195

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