Synlett
DOI: 10.1055/s-0036-1590826
cluster
© Georg Thieme Verlag Stuttgart · New York

Synthesis of Stereoselectively Functionalized Silacyclopentanes

Kazunobu Igawa*a, b, Akihiro Kuroob, Daisuke Yoshihirob, Yuki Yamanakab, Katsuhiko Tomooka*a, b
  • aInstitute for Materials Chemistry and Engineering and IRCCS, Kyushu University, Kasuga, Fukuoka 816-8580, Japan   Email: kigawa@cm.kyushu-u.ac.jp   Email: ktomooka@cm.kyushu-u.ac.jp
  • bDepartment of Molecular and Material Sciences, Kyushu University, Kasuga, Fukuoka 816-8580, Japan
This research was supported by JSPS KAKENHI Grants JP16K13955, JP15K13697, and 17H06235, Integrated Research Consortium on Chemical Sciences, the Cooperative Research Program of ‘Network Joint Research Center for Materials and Devices’, Kakihara Science Technology Foundation, and Ube Industries Foundation.
Further Information

Publication History

Received: 16 May 2017

Accepted: 12 June 2017

Publication Date:
25 August 2017 (eFirst)

Dedicated to Professor Teruaki Mukaiyama in celebration of his 90th birthday (Sotsuju)

Published as part of the Cluster Silicon in Synthesis and Catalysis

Abstract

An efficient approach to a variety of chiral silacyclopentanes having silicon stereogenic center based on the stereospecific transformations of C4 carbon stereogenic center of silacyclopentenols by ­Mitsunobu reaction or Tsuji–Trost reaction has been developed. The thus obtained substitution products can be converted into novel silacyclopentane triols, amines, and carboxylic acids in stereospecific manner.

Supporting Information