Abstract
A convenient and efficient procedure for regio- and diastereoselective addition of prenyl and geranyl anions to ethyl propiolate is reported. This 1,4-addition reaction produces exclusively the trans isomer at the double bond deriving from the triple bond of ethyl propiolate without rearrangement of the starting primary, allylic carbanion nucleophile.
Notes
1H NMR (300MHz, CDCl3): 5.62 (1H, t), 1.65 (2H, d), 1.62 (2H, d), 1.55 (3H, s), 1.47 ∼ 1.21 (6H,m), 0.87 (3H,t).
1H NMR (300MHz, CDCl3): 5.30 (1H, t), 5.08 (1H,t), 1.99 (4H,m), 1.66 (3H,s), 1.62 (2H, d), 1.58 (3H,s), 1.55(3H,s), 1.45 (2H, d), 1.33–1.17 (4H,m), 0.86 (3H,t).