Abstract
α-Aminoalkylcuprates prepared from tert-butoxycarbonyl protected amines undergo a conjugate addition reaction with α,β-β,γ-allenyl esters to afford the corresponding β,γ-unsaturated esters with high degree of stereoselectivity. Treatment of the unsaturated esters with PhOH TMSCl or catechol boron bromide effects amine deprotection and lactamization to afford a 4-alkylidene-2-pyrrolidinone ring with preservation of the original olefin stereochemistry. The method can be used to prepare 4-alkylidene 2-pyrrolidinones and 2-pyrrolizidinones
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