Prev. Article Next Article Table of Contents

Communication

Skeletal Reorganization of Enynes to 1-Vinylcycloalkenes Catalyzed by GaCl₃

Supporting Info

Naoto Chatani,* Hiroki Inoue, Taiichi Kotsuma, and Shinji Murai

Department of Applied Chemistry, Faculty of Engineering, Osaka University, Suita, Osaka 565-0871, Japan

J. Am. Chem. Soc., 2002, 124 (35), pp 10294–10295

DOI: 10.1021/ja0274554

Publication Date (Web): August 9, 2002

To whom correspondence should be addressed. E-mail: chatani@ chem.eng.osaka-u.ac.jp.

Abstract

The skeletal reorganization of enynes is achieved by the presence of GaCl₃ as the catalyst. This reaction demonstrates the first example of the skeletal reorganization of enynes catalyzed by typical metal complexes. The process is simple and provides a diverse range of enynes in good to high yields. The reaction of enynes bearing a monosubstituent at the terminal olefinic carbon proceeds in a stereospecific manner with respect to the geometry of the olefin moiety. Enynes, bearing two substituents at the olefinic terminal carbon, undergo an efficient skeletal reorganization, these substrates having been known to be unsuitable substrates for the skeletal reorganization of enynes.

View: Full Text HTML | Hi-Res PDF

Tools

SciFinder Links

History

Published In Issue September 04, 2002
Received June 25, 2002

Recommend & Share

Related Content

Ga(III)-Catalyzed Cycloisomerization Strategy for the Synthesis of Icetexane Diterpenoids: Total Synthesis of (±)-SalviasperanolOrganic Letters
- Ga(III)-Catalyzed Cycloisomerization Strategy for the Synthesis of Icetexane Diterpenoids: Total Synthesis of (±)-Salviasperanol
  Eric M. Simmons and Richmond Sarpong
  Organic Letters 2006 8 (13), pp 2883–2886
  Abstract: A general approach to the tricyclic core of the icetexane natural products via the cycloisomerization of alkynyl indenes using GaCl₃ is presented. This strategy provides an efficient synthesis of the natural product salviasperanol and sets the stage for ...
  Abstract | Full Text HTML | Hi-Res PDF
Catalytic [4+1] Cycloaddition of α,β-Unsaturated Carbonyl Compounds with IsocyanidesJournal of the American Chemical Society
- Catalytic [4+1] Cycloaddition of α,β-Unsaturated Carbonyl Compounds with Isocyanides
  Masayuki Oshita, Kohei Yamashita, Mamoru Tobisu, and Naoto Chatani
  Journal of the American Chemical Society 2005 127 (2), pp 761–766
  Abstract: The GaCl₃-catalyzed [4+1] cycloaddition reactions of α,β-unsaturated ketones with isocyanides leading to lactone derivatives are described. While some other Lewis acids also show catalytic activity, GaCl₃ was the most efficient catalyst. The reaction is ...
  Abstract | Full Text HTML | Hi-Res PDF
Skeletal Reorganization of Enynes Catalyzed by InCl₃Organic Letters
- Skeletal Reorganization of Enynes Catalyzed by InCl₃
  Yuhei Miyanohana and Naoto Chatani
  Organic Letters 2006 8 (10), pp 2155–2158
  Abstract: The skeletal reorganization of enynes is achieved by the presence of InCl₃ as the catalyst. The reaction of enynes having a terminal acetylenic moiety proceeds in a stereospecific manner to give 1-vinylcycloalkenes. The reaction of enynes containing an ...
  Abstract | Full Text HTML | Hi-Res PDF

Communication

Skeletal Reorganization of Enynes to 1-Vinylcycloalkenes Catalyzed by GaCl₃