K. Tago, H. Kogen
Jun 3, 2000
Citations
0
Influential Citations
33
Citations
Journal
Organic letters
Abstract
A novel reagent, methyl bis(2,2,2-trifluoroethoxy)bromophosphonoacetate (3a), was designed and prepared in order to efficiently synthesize (E)-alpha-bromoacrylates, which are useful precursors for various C-C bond formations. Honer-Wadsworth-Emmons (HWE) reaction of various aldehydes with 3a in the presence of t-BuOK and 18-C-6 gave the corresponding (E)-alpha-bromoacrylate derivatives with high stereoselectivity. Using the (E)-alpha-bromoacrylate as a key intermediate, a general stereoselective synthesis of trisubstituted alkenes via Pd-catalyzed cross-coupling was developed.