One-pot synthesis of homoallylic ketones from the addition of vinyl grignard reagent to carboxylic esters.
Fifteen homoallylic ketones have been synthesized in 26-77% yields on treatment of aromatic, aliphatic, and alpha-amino methyl carboxylates with excess vinylmagnesium bromide and catalytic amounts of a copper salt in THF. Alpha-amino homoallylic ketones derived from N-protected alpha-amino esters possessing aliphatic and alcohol side chains were synthesized in > or =98% enantiomeric purity. [reaction: see text]
Hansford
Karl A
KA
Département de Chimie, Université de Montréal, C.P. 6128, Succursale Centre Ville, Montréal, Québec, Canada H3C 3J7.
Dettwiler
James E
JE
Lubell
William D
WD