Abstract
Reactive organometallic compounds such as allyl-zinc, -magnesium,-lithium and saturated lithium compounds are shown to readily undergo addition reactions with functionally conjugated enynes: HCCC(R)C(R′)(CH 2) n R″ (R″ = OH, OC 4H 9, NHC 2H 5N(C 2H 5) 2), but the reactivity is reduced when the steric hindrance around the double bond is increased. With each organometallic compound used, this reaction is regioselective: 3,4 addition with organozinc compounds, 1,2 addition with organolithium compounds (allyl-, butyl-) and both 1,2 and 1,4 addition with organomagnesium compounds.
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