Collect. Czech. Chem. Commun. 1996, 61, 1697-1702

Solid-Phase Organic Synthesis: Creation of Carbon-Carbon Double Bonds Under Mild Conditions by Wittig-Type Reactions

Josef Vágnera, Viktor Krchňákb, Michal Leblb and George Baranya

a Department of Chemistry, University of Minnesota, 207 Pleasant Street S.E., Minneapolis, MN 55455, U.S.A.
b Selectide Corporation, an Affiliate of Hoechst Marion Roussel, 1580 E. Hanley Boulevard, Tucson, AZ 85737, U.S.A.


Phosphorane ylides and phosphonate anions react smoothly with resin-bound aldehydes and ketones to provide alkenes in good yields and purities (assessed after cleavage of acid-labile PAL anchor to support). The reactions of aldehydes give excellent stereoselectivities. Effective conditions have been developed for carrying out these transformations.

Keywords: Solid-phase synthesis; Combinatorial chemistry; Wittig reaction.