Ruthenium-catalyzed cross-coupling of tertiary propargyl alcohols with omega-alkynenitriles: a regio- and stereoselective surrogate for an aldol condensation.
A novel catalytic alkyne cross-coupling reaction is reported which connects tertiary propargyl alcohols with omega-alkynylnitriles with perfect atom economy. This remarkable process generates highly functionalized, stereodefined dienones that are formal aldol products in a single step. Moreover, the specificity of the cyano substituent for this reaction demonstrates the unique and somewhat underappreciated properties of that functional group.
Trost
Barry M
BM
Department of Chemistry, Stanford University, Stanford, California 94305-5080, USA. bmtrost@stanford.edu
Maulide
Nuno
N
Rudd
Michael T
MT