Double-Allylation Reagents for Stereoselective Reactions

doi:10.1055/s-2007-968499

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Synfacts 2007(6): 0630-0630
DOI: 10.1055/s-2007-968499

Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions

Double-Allylation Reagents for Stereoselective Reactions

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

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Publikationsdatum:
22. Mai 2007 (online)

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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.