Remarkable phosphine-effect on the intramolecular aldol reactions of unsaturated 1,5-diketones: highly regioselective synthesis of cross-conjugated dienones.

ABSTRACT: We report a phosphine-mediated intramolecular aldol cyclization of unsaturated diketones that proceeds with extremely high levels of regioselectivity for the cross-conjugated bicyclic dienone products. The sense of regioselectivity observed in this reaction is complementary to that obtained using traditional aldol conditions. Experimental evidence that supports the involvement of a phosphine Michael adduct is described.

SUBMITTER: Thalji RK 

PROVIDER: S-EPMC2515627 | biostudies-literature | 2005 Dec

REPOSITORIES: biostudies-literature