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  • Title: Zinc-catalyzed allenylations of aldehydes and ketones.
    Author: Fandrick DR, Saha J, Fandrick KR, Sanyal S, Ogikubo J, Lee H, Roschangar F, Song JJ, Senanayake CH.
    Journal: Org Lett; 2011 Oct 21; 13(20):5616-9. PubMed ID: 21942658.
    Abstract:
    The general zinc-catalyzed allenylation of aldehydes and ketones with an allenyl boronate is presented. Preliminary mechanistic studies support a kinetically controlled process wherein, after a site-selective B/Zn exchange to generate a propargyl zinc intermediate, the addition to the electrophile effectively competes with propargyl-allenyl zinc equilibration. The utility of the methodology was demonstrated by application to a rhodium-catalyzed [4+2] cycloaddition.
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