Synfacts 2008(2): 0195-0195  
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

Contributor(s): Paul Knochel, Andrei Gavryushin
R. J. Fox, G. Lalic, R. Bergman*
University of California, Berkeley, USA
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23. Januar 2008 (online)


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.