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Diastereospecific nazarov cyclization of fully substituted dienones: generation of vicinal all-carbon-atom quaternary stereocenters.

ABSTRACT: No vacancy: Fully substituted dienones that are highly polarized by a vinylogous carbonate group were found to undergo a remarkably rapid and diastereospecific Nazarov cyclization that led to cyclopentenones with vicinal all-carbon-atom quaternary centers (see example; SEM=2-(trimethylsilyl)ethoxymethyl, Tf=trifluoromethanesulfonyl).

SUBMITTER: Jolit A

PROVIDER: S-EPMC3872134 | biostudies-literature | 2013 Oct

REPOSITORIES: biostudies-literature

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Diastereospecific nazarov cyclization of fully substituted dienones: generation of vicinal all-carbon-atom quaternary stereocenters.

Jolit Anais A Vazquez-Rodriguez Saleta S Yap Glenn P A GP Tius Marcus A MA

Angewandte Chemie (International ed. in English) 20130903 42

No vacancy: Fully substituted dienones that are highly polarized by a vinylogous carbonate group were found to undergo a remarkably rapid and diastereospecific Nazarov cyclization that led to cyclopentenones with vicinal all-carbon-atom quaternary centers (see example; SEM=2-(trimethylsilyl)ethoxymethyl, Tf=trifluoromethanesulfonyl). ...[more]

PMID: 24002922

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