The first stereoselective Ficini-Claisen rearrangement using chiral ynamides

Jason A Mulder; Richard P Hsung; Michael O Frederick; Michael R Tracey; Craig A Zificsak

doi:10.1021/ol020037j

The first stereoselective Ficini-Claisen rearrangement using chiral ynamides

Org Lett. 2002 Apr 18;4(8):1383-6. doi: 10.1021/ol020037j.

Authors

Jason A Mulder¹, Richard P Hsung, Michael O Frederick, Michael R Tracey, Craig A Zificsak

Affiliation

¹ Department of Chemistry, University of Minnesota, Minneapolis, MN 55455, USA.

PMID: 11950368
DOI: 10.1021/ol020037j

Abstract

The first asymmetric Ficini-Claisen rearrangement using chiral ynamides is described. At relatively low temperatures, the Ficini-Claisen rearrangement can be efficiently promoted by p-nitrobenzenesulfonic acid leading to high diastereoselectivity for a range of different allylic alcohols and chiral ynamides. [reaction: see text]