Zinc-Catalyzed Allenylations of Aldehydes and Ketones

• DOI: 10.1021/ol202343c
• Publication Date: 2011-09-26T14:59:22Z
• Authors: Daniel R. Fandrick; Jaideep Saha; Keith R. Fandrick; Sanjit Sanyal; Junichi Ogikubo; Heewon Lee; Frank Roschangar; Jinhua J. Song; Chris H. Senanayake
• Keywords: Propargyl

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 site-selective B/Zn exchange to generate propargyl zinc intermediate, the addition electrophile effectively competes propargyl-allenyl equilibration. utility methodology was demonstrated by application rhodium-catalyzed [4+2] cycloaddition.