The First Stereoselective Ficini−Claisen
Rearrangement Using Chiral Ynamides

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

doi:10.1021/ol020037j.s001

ol020037j_si_001.pdf (952.25 kB)

The First Stereoselective Ficini−Claisen Rearrangement Using Chiral Ynamides

journal contribution

posted on 2002-03-22, 00:00 authored by Jason A. Mulder, Richard P. Hsung, Michael O. Frederick, Michael R. Tracey, Craig A. Zificsak

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.