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  • Title: Gold(I)-catalyzed ring expansion of cyclopropanols and cyclobutanols.
    Author: Markham JP, Staben ST, Toste FD.
    Journal: J Am Chem Soc; 2005 Jul 13; 127(27):9708-9. PubMed ID: 15998074.
    Abstract:
    The rearrangement of 1-alkynyl cyclobutanols and cyclopropanols to alkylidene cycloalkanones catalyzed by cationic triarylphosphine gold(I) complexes is described. The reaction tolerates terminal alkynes as well as alkyl, aryl, and halo-substitution at the acetylenic position and stereoselectively provides a single olefin isomer. The gold(I)-catalyzed rearrangement is stereospecific with regard to substituents on the ring, thus providing a practical method for the stereoselective synthesis of highly substituted cyclopentanones from cyclopropanols. The reaction stereoselectively provides a single olefin isomer and is stereospecific with regard to substituents on the ring via sequential gold(I)-catalyzed ring expansion reactions.
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