Highly stereoselective Saucy-Marbet rearrangement using chiral ynamides. Synthesis of highly substituted chiral homoallenyl alcohols.
[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.
Frederick
Michael O
MO
Department of Chemistry, University of Minnesota, Minneapolis, Minnesota 55455, USA.
Hsung
Richard P
RP
Lambeth
Robert H
RH
Mulder
Jason A
JA
Tracey
Michael R
MR