Substituent effects on 1–2 versus 1–4 addition of lithiated arylacetonitriles to 2-cyclohexenones in tetrahydrofuran

Abstract

The reaction of organolithium derivates with α β unsaturated ketones gives, generally, allylic alcohols resulting from 1–2 addition (1). Recently, it has been shown that 1–4 addition products can be obtained in diethyl ether or in tetrahydrofuran (THF) either under kinetic control (2), mainly when the carbonyl group is sterically hindered (3,4), or under thermodynamic control when the lithiated reagent is substituted by electron delocalizing groups (5–16).