Reaction of substituted 2-picolyllithiums with epoxides

ORGN 356

James R. Vyvyan, vyvyan@chem.wwu.edu1, Rebecca C. Brown, brownr26@cc.wwu.edu1, and Brian P. Woods, woodsbp@whitman.edu2. (1) Department of Chemistry, Western Washington University, 516 High Street, Bellingham, WA 98225-9150, (2) Department of Chemistry, Whitman College, Walla Walla, WA 99362
Substituted 2-picolyllithium species were reacted with monosubstuted and trisubstituted epoxides to produce the corresponding adducts. Reactions were run in the presence and absence of the additives BF3 etherate and HMPA. 1,2-Epoxyoctane reacted efficiently with the anion derived from 2,6-lutidine and the sulfide-substituted lutidine derivative. Lower yields were obtained with the sulfone and nitrile substrates, however. The trisubstuted epoxide gave low yields of adducts with all anions studied. These results will be discussed in the context of a proposed synthesis of the anti-cancer alkaloid cananodine.

 

Heterocycles and Aromatics, Molecular Recognition and Self Assembly
8:00 PM-10:00 PM, Tuesday, April 8, 2008 Morial Convention Center -- Hall A, Poster

Division of Organic Chemistry

The 235th ACS National Meeting, New Orleans, LA, April 6-10, 2008