Synlett
DOI: 10.1055/s-0036-1588522
letter
© Georg Thieme Verlag Stuttgart · New York

Consecutive Aminolithiation–Carbolithiation of a Linear Aminoalkene Bearing Terminal Vinyl Sulfide Moiety to Give Hydro­indolizine

Yasutomo Yamamoto*a, Tatsuya Yamaguchib, Atsunori Kaneshigeb, Aiko Hashimotoa, Sachiho Kaibea, Akari Miyawakia, Ken-ichi Yamadab, Kiyoshi Tomioka*a, b
  • aFaculty of Pharmaceutical Sciences, Doshisha Women’s College of Liberal Arts, Kodo, Kyotanabe 610-0395, Japan   Email: ktomioka@dwc.doshisha.ac.jp
  • bGraduate School of Pharmaceutical Sciences, Kyoto University, Yoshida, Sakyo-ku, Kyoto 606-8501, Japan
Further Information

Publication History

Received: 08 June 2017

Accepted after revision: 04 July 2017

Publication Date:
08 August 2017 (eFirst)

This paper is dedicated to Professor Victor Snieckus on the occasion of his 80th birthday

Abstract

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.

Supporting Information