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Kinetic versus Thermodynamic Stereoselectivity in the Hydrostannylation of Propargylic Alcohol Derivatives Using AIBN and Et3B as Promotors

Authors

  • Martins S. Oderinde,

    1. Department of Chemistry, York University, 4700 Keele Street, Toronto, ON, M3J 1P3 (Canada), Fax: (+1) 416-736-5936
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  • Dr. Howard N. Hunter,

    1. Department of Chemistry, York University, 4700 Keele Street, Toronto, ON, M3J 1P3 (Canada), Fax: (+1) 416-736-5936
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  • Prof. Michael G. Organ

    Corresponding author
    1. Department of Chemistry, York University, 4700 Keele Street, Toronto, ON, M3J 1P3 (Canada), Fax: (+1) 416-736-5936
    • Department of Chemistry, York University, 4700 Keele Street, Toronto, ON, M3J 1P3 (Canada), Fax: (+1) 416-736-5936
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  • AIBN=2-2′-azobisisobutyronitrile.

Abstract

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Et3B versus AIBN: Equally radical? The stereoselectivity of hydrostannylation of internal propargyl alcohol derivatives has been studied by using both 2-2′-azobisisobutyronitrile (AIBN) and Et3B as promoters. With silyl-protected alcohols, complete Z selectivity of the resultant vinylstannane has been achieved with Et3B, whereas AIBN shows zero stereoselectivity. Evidence suggests that, despite decades of acceptance, the hydrostannylation mechanisms employing Et3B and AIBN appear to be mechanistically distinct.

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