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Asymmetric synthesis of medium-sized rings by intramolecular Au(I)-catalyzed cyclopropanation.

ABSTRACT: An efficient method for the asymmetric gold(I)-catalyzed preparation of medium sized rings has been developed. The method provides 7- to 9-membered rings in excellent yield. High enantioselectivities can be achieved for 7- and 8-membered ring products employing chiral gold(I) complexes. The results provide insight into the mechanism, showing the fluxional nature of gold(I)-stabilized vinyl carbenoid intermediates.

SUBMITTER: Watson ID

PROVIDER: S-EPMC2662771 | biostudies-literature | 2009 Feb

REPOSITORIES: biostudies-literature

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Asymmetric synthesis of medium-sized rings by intramolecular Au(I)-catalyzed cyclopropanation.

Watson Iain D G ID Ritter Stefanie S Toste F Dean FD

Journal of the American Chemical Society 20090201 6

An efficient method for the asymmetric gold(I)-catalyzed preparation of medium sized rings has been developed. The method provides 7- to 9-membered rings in excellent yield. High enantioselectivities can be achieved for 7- and 8-membered ring products employing chiral gold(I) complexes. The results provide insight into the mechanism, showing the fluxional nature of gold(I)-stabilized vinyl carbenoid intermediates. ...[more]

PMID: 19161306

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