Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 74, Issue 15, Pages 5326-5330Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jo900808k
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Funding
- National Natural Science Foundation of China [20672133, 20702059, 20732008]
- Chinese Academy of Science
- Science and Technology Commission of Shanghai Municipality
- Major State Basic Research Development Program [2006CB806105]
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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.
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