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Synfacts 2008(2): 0195-0195
DOI: 10.1055/s-2007-992476
DOI: 10.1055/s-2007-992476
Metal-Mediated Synthesis
© Georg Thieme Verlag Stuttgart · New York
Protected Allylic Alcohols via Selective SN2′ Substitution of Allylic Chlorides
R. J. Fox, G. Lalic, R. Bergman*
University of California, Berkeley, USA
Further Information
Publication History
Publication Date:
23 January 2008 (online)
Significance
The group of Bergman describes herein a simple and interesting method for the transformation of allylic chlorides into the corresponding γ-OTBS-ethers using a soluble oxo-zirconium complex. The reaction tolerates various functionalities and proceeds under certain conditions exclusively via SN2′ mechanism, thus affording the complete conservation of enantioselectivity. This elegant method may be useful in the synthesis of complex natural products. Besides, kinetic and mechanistic studies of this process are reported.