Zinc-Catalyzed Allenylations of Aldehydes and Ketones
Organic Letters2011Vol. 13(20), pp. 5616–5619
Citations Over TimeTop 12% of 2011 papers
Daniel R. Fandrick, Jaideep Saha, Keith R. Fandrick, Sanjit Sanyal, Junichi Ogikubo, Heewon Lee, Frank Roschangar, Jinhua J. Song, Chris H. Senanayake
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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