Facile Preparation of Various Heteroaromatic Compounds via Azatitanacyclopentadiene Intermediates

Daisuke Suzuki,† Youhei Nobe,‡ Yuko Watai,‡ Ryoichi Tanaka,‡ Yuuki Takayama,† Fumie Sato,*† and Hirokazu Urabe*†‡;
Contribution from the Departments of Biomolecular Engineering and Biological Information, Graduate School of Bioscience and Biotechnology, Tokyo Institute of Technology, 4259-B-59 Nagatsuta-cho, Midori-ku, Yokohama, Kanagawa 226-8501, Japan
J. Am. Chem. Soc., 2005, 127 (20), pp 7474–7479
DOI: 10.1021/ja0502730
Publication Date (Web): April 27, 2005
Copyright © 2005 American Chemical Society
†

 Department of Biomolecular Engineering.

,
‡

 Department of Biological Information.

,
*

In papers with more than one author, the asterisk indicates the name of the author to whom inquiries about the paper should be addressed.

, hurabe@bio.titech.ac.jp, ; , fsato@bio.titech.ac.jp.

Abstract

Abstract Image

Coupling of acetylene, nitrile, and a titanium reagent, Ti(O-i-Pr)4/2 i-PrMgCl, generated new azatitanacyclopentadienes in a highly regioselective manner. Their subsequent reaction with sulfonylacetylene afforded pyridyltitanium compounds, which, upon reaction with electrophiles, gave substituted pyridines virtually as a single isomer. When optically active nitriles were used in this reaction, chiral pyridines were obtained without loss of the enantiopurity. Alternatively, the azatitanacyclopentadiene prepared from an unsymmetrical acetylene reacted with an aldehyde or another nitrile to give furans or pyrroles having four different substituents again in a regioselective manner.

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History

  • Published In Issue May 25, 2005
  • Received January 14, 2005

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