Consecutive Aminolithiation–Carbolithiation of a Linear Aminoalkene Bearing Terminal Vinyl Sulfide Moiety to Give Hydroindolizine
Received: 08 June 2017
Accepted after revision: 04 July 2017
08 August 2017 (eFirst)
This paper is dedicated to Professor Victor Snieckus on the occasion of his 80th birthday
Aminolithiation–carbolithiation tandem cyclization of an aminoalkene bearing vinyl sulfide moiety proceeded smoothly using stoichiometric amounts of BuLi. Both aminolithiation and carbolithiation were in equilibrium at room temperature, and the stereochemistry of the cyclization was thermodynamically controlled. At –78 °C the reaction was kinetically controlled and the cyclized product, 1,2-disubstituted octahydroindolizine, was obtained with good diastereoselectivity.