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A ring fragmentation approach to medium-sized cyclic 2-alkynones.

ABSTRACT: Bicyclic ?-silyloxy-?-hydroxy-?-diazoketones, in which the C?-C? bond is the ring fusion bond, productively fragment when treated with tin(IV) chloride to provide medium-sized cyclic 2-alkynones. This method provides good to excellent yields of 10-, 11-, and 12-membered alkynone products.

SUBMITTER: Tsvetkov NP

PROVIDER: S-EPMC3253231 | biostudies-literature | 2012 Jan

REPOSITORIES: biostudies-literature

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A ring fragmentation approach to medium-sized cyclic 2-alkynones.

Tsvetkov Nikolay P NP Bayir Ali A Schneider Samuel S Brewer Matthias M

Organic letters 20111201 1

Bicyclic γ-silyloxy-β-hydroxy-α-diazoketones, in which the Cβ-Cγ bond is the ring fusion bond, productively fragment when treated with tin(IV) chloride to provide medium-sized cyclic 2-alkynones. This method provides good to excellent yields of 10-, 11-, and 12-membered alkynone products. ...[more]

PMID: 22132946

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