Abstract
The reaction of alkyl triflates 1 or allyl or benzyl triflamides 3 with an excess of lithium powder and a catalytic amount of naphthalene (4 mol %) in the presence of different electrophiles [Me 3SiCl, Pr iCHO, Bu tCHO, PhCHO, 4-MeOC 6H 4CHO, CH 3(CH 2) 6CHO, Et 2CO, (CH 2) 5CO, ( c-C 3H 5) 2CO, PhCOMe, 4-MeC 6H 4COPh, PhCH=NPh, n-C 8H 7CON(CH 2) 4] in THF at temperature ranging between −78 and 0°C leads, after hydrolysis with water, to the corresponding condensation products 2. When α,β-unsaturated carbonyl compounds are used as electrophilic compounds 1,2- (2-cyclohexenone) or 1,4-addition (cinnamaldehyde or benzylideneacetone) takes places depending on the electrophile used.
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