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Stereoselective, dual-mode ruthenium-catalyzed ring expansion of alkynylcyclopropanols.

ABSTRACT: A novel, dual-pathway ring expansion of alkynylcyclopropanols is described. On treatment with a ruthenium catalyst, these compounds undergo highly selective enlargement to either (Z)-alkylidene cyclobutanones or beta-substituted cyclopentenones. The unique ability to access the least selective double bond isomers of alkylidene cyclobutanones and the dramatic shift of reactivity observed further illustrate the particular intricacies of ruthenium catalysis when compared to other alkynophilic transition metals.

SUBMITTER: Trost BM

PROVIDER: S-EPMC2655345 | biostudies-literature | 2008 Dec

REPOSITORIES: biostudies-literature

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Stereoselective, dual-mode ruthenium-catalyzed ring expansion of alkynylcyclopropanols.

Trost Barry M BM Xie Jia J Maulide Nuno N

Journal of the American Chemical Society 20081201 51

A novel, dual-pathway ring expansion of alkynylcyclopropanols is described. On treatment with a ruthenium catalyst, these compounds undergo highly selective enlargement to either (Z)-alkylidene cyclobutanones or beta-substituted cyclopentenones. The unique ability to access the least selective double bond isomers of alkylidene cyclobutanones and the dramatic shift of reactivity observed further illustrate the particular intricacies of ruthenium catalysis when compared to other alkynophilic trans ...[more]

PMID: 19053484

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