Synfacts 2007(6): 0630-0630  
DOI: 10.1055/s-2007-968499
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York

Double-Allylation Reagents for Stereoselective Reactions

Contributor(s): Hisashi Yamamoto, Matthew B. Boxer
F. Peng, D. G. Hall*
University of Alberta, Edmonton, Canada
Further Information

Publication History

Publication Date:
22 May 2007 (online)

Significance

The Hall group has extended their work on allylation to include a very interesting molecule containing an allyl-boron and homo-allyl silyl group for a cascade-type, double allylation reagent. Very high ee values were obtained for the first (allyl boron) allylation under BF3×OEt2 conditions. Adding aldehydes and TMSOTf for the second allylation (allyl silane) provided substituted furans with high diastereoselectivity and concomitant high ee values.