Stork-Danheiser Reaction

Post date: Nov 15, 2016 10:06:59 PM

The Stork-Danheiser Reaction was used in the Stoltz synthesis of Cassiol (2009): Org. Lett. 2009 11 293. The Stork-Danheiser reaction is a neat way of taking advantage of the vinylogous ester's electrophilic carbonyl to install a nucleophile while ultimately "switching" the position of the carbonyl! You start from one alpha-beta unsaturated carbonyl and end up at another alpha-beta unsaturated carbonyl! It is a useful way to make substituted cyclohexenones.

Image Sources:

Baran Group Meeting (chemistry of Gilbert Stork): https://www.scripps.edu/baran/images/grpmtgpdf/Burns_May_06.pdf

Chemistry By Design http://chemistrybydesign.oia.arizona.edu/