Synlett 2017; 28(20): 2913-2917
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   Faculty of Pharmaceutical Sciences, Doshisha Women’s College of Liberal Arts, Kodo, Kyotanabe 610-0395, Japan   eMail: ktomioka@dwc.doshisha.ac.jp
,
Tatsuya Yamaguchi
b   Graduate School of Pharmaceutical Sciences, Kyoto University, Yoshida, Sakyo-ku, Kyoto 606-8501, Japan
,
Atsunori Kaneshige
b   Graduate School of Pharmaceutical Sciences, Kyoto University, Yoshida, Sakyo-ku, Kyoto 606-8501, Japan
,
Aiko Hashimoto
a   Faculty of Pharmaceutical Sciences, Doshisha Women’s College of Liberal Arts, Kodo, Kyotanabe 610-0395, Japan   eMail: ktomioka@dwc.doshisha.ac.jp
,
Sachiho Kaibe
a   Faculty of Pharmaceutical Sciences, Doshisha Women’s College of Liberal Arts, Kodo, Kyotanabe 610-0395, Japan   eMail: ktomioka@dwc.doshisha.ac.jp
,
Akari Miyawaki
a   Faculty of Pharmaceutical Sciences, Doshisha Women’s College of Liberal Arts, Kodo, Kyotanabe 610-0395, Japan   eMail: ktomioka@dwc.doshisha.ac.jp
,
Ken-ichi Yamada
b   Graduate School of Pharmaceutical Sciences, Kyoto University, Yoshida, Sakyo-ku, Kyoto 606-8501, Japan
,
Kiyoshi Tomioka*
a   Faculty of Pharmaceutical Sciences, Doshisha Women’s College of Liberal Arts, Kodo, Kyotanabe 610-0395, Japan   eMail: ktomioka@dwc.doshisha.ac.jp
b   Graduate School of Pharmaceutical Sciences, Kyoto University, Yoshida, Sakyo-ku, Kyoto 606-8501, Japan
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Publikationsverlauf

Received: 08. Juni 2017

Accepted after revision: 04. Juli 2017

Publikationsdatum:
08. August 2017 (online)


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

 
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