Highly Stereoselective Saucy−Marbet Rearrangement Using Chiral Ynamides. Synthesis of Highly Substituted Chiral Homoallenyl Alcohols
- 19 June 2003
- journal article
- Published by American Chemical Society (ACS) in Organic Letters
- Vol. 5 (15) , 2663-2666
- https://doi.org/10.1021/ol030061c
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.Keywords
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