title: Highly stereoselective Saucy-Marbet rearrangement using chiral ynamides. Synthesis of highly substituted chiral homoallenyl alcohols.
abstract: [reaction: see text] A highly stereoselective Saucy-Marbet rearrangement using chiral ynamides and propargyl alcohols is described here. This rearrangement can be catalyzed by para-nitrobenzenesulfonic acid leading to high diastereoselectivities for a range of different chiral propargyl alcohols and ynamides in a stereochemically intriguing matched, mismatched, or indifferent manner. This provides an excellent entry to highly substituted chiral homoallenyl alcohols.
authors.affiliation: Department of Chemistry, University of Minnesota, Minneapolis, Minnesota 55455, USA.
authors.forename: Michael O
authors.initials: MO
authors.lastname: Frederick
authors.forename: Richard P
authors.initials: RP
authors.lastname: Hsung
authors.forename: Robert H
authors.initials: RH
authors.lastname: Lambeth
authors.forename: Jason A
authors.initials: JA
authors.lastname: Mulder
authors.forename: Michael R
authors.initials: MR
authors.lastname: Tracey