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Intercepting the Breslow intermediate via Claisen rearrangement: synthesis of complex tertiary alcohols without organometallic reagents.

ABSTRACT: A novel Claisen rearrangement in which the Breslow intermediate is engaged as a hydroxy-substituted N,S-ketene acetal to provide complex 3° alcohols without the use of organometallic reagents is reported. The reaction constitutes an unprecedented reactivity mode for the Breslow intermediate.

SUBMITTER: Alwarsh S

PROVIDER: S-EPMC3572745 | biostudies-literature | 2013 Jan

REPOSITORIES: biostudies-literature

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Intercepting the Breslow intermediate via Claisen rearrangement: synthesis of complex tertiary alcohols without organometallic reagents.

Alwarsh Sefat S Ayinuola Kolawole K Dormi Silvana S SS McIntosh Matthias C MC

Organic letters 20121205 1

A novel Claisen rearrangement in which the Breslow intermediate is engaged as a hydroxy-substituted N,S-ketene acetal to provide complex 3° alcohols without the use of organometallic reagents is reported. The reaction constitutes an unprecedented reactivity mode for the Breslow intermediate. ...[more]

PMID: 23214715

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