Consecutive approach to alkenes that combines radical addition of phosphorus hydrides with Horner-Wadsworth-Emmons-type reactions.
[reaction: see text] Addition of diethyl thiophosphite to terminal alkenes, in the presence of a radical initiator, followed by deprotonation of the phosphonothioate and reaction with a ketone, offers a concise one-pot approach to substituted alkenes. This novel method, which can incorporate alkylation or acylation steps, can be applied to the stereoselective formation of sterically hindered tri- and tetrasubstituted alkenes.
Healy
Mark P
MP
Department of Chemistry, University of York, Heslington, York, YO10 5DD, UK, and GlaxoSmithKline, New Frontiers Science Park, Third Avenue, Harlow, Essex CM19 5AW, UK.
Parsons
Andrew F
AF
Rawlinson
James G T
JG