Stereoselective synthesis of beta-hydroxyallenes with multiple contiguous stereogenic centers via aldehyde addition to alpha-alkenyl-substituted zirconacyclopentenes.

Journal Article (Journal Article)

A highly stereoselective methodology for the synthesis of beta-hydroxyallenes with multiple stereogenic centers including allenic axial chirality, as well as center chirality, via addition of alpha-alkenylzirconacyclopentenes to aldehyde is described. Remarkably, the reaction occurs with completely different chemoselectivity in comparison with the usual alkyl- or aryl-substituted zirconacyclopentenes; that means, the C-C bond formation occurred selectively at the alkenylic carbon substituted with phenyl or alkyl group, while in the latter cases, insertion of aldehydes into the alkyl-zirconium bond to afford seven-membered oxazirconacycles has usually been observed.

Full Text

Duke Authors

Cited Authors

  • Zhou, Y; Chen, J; Zhao, C; Wang, E; Liu, Y; Li, Y

Published Date

  • August 7, 2009

Published In

Volume / Issue

  • 74 / 15

Start / End Page

  • 5326 - 5330

PubMed ID

  • 19572574

Electronic International Standard Serial Number (EISSN)

  • 1520-6904

Digital Object Identifier (DOI)

  • 10.1021/jo900808k


  • eng

Conference Location

  • United States