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Synlett 2011(7): 1015-1017  
DOI: 10.1055/s-0030-1259930
LETTER
© Georg Thieme Verlag Stuttgart ˙ New York

Indium-Catalyzed Synthesis of Furans and Pyrroles via Cyclization of α-Propargyl-β-keto Esters

Hayato Tsuji*, Ken-ichi Yamagata, Yasuyuki Ueda, Eiichi Nakamura*
Department of Chemistry, School of Science, The University of Tokyo, 7-3-1, Hongo, Bunkyo-ku, Tokyo 113-0033, Japan
Fax: +81(3)58006889; e-Mail: nakamura@chem.s.u-tokyo.ac.jp;
Further Information

Publication History

Received 2 December 2010
Publication Date:
29 March 2011 (online)

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Abstract

In(OTf)3 or In(NTf2)3 effectively catalyze the cyclo­isomerization reaction of α-propargyl-β-keto esters and their imine analogues to afford trisubstituted furans and pyrroles, respectively. Both terminal and internal alkynes take part in the reaction with good functional-group compatibility in the presence of only a small amount of the catalyst.

Key words

indium catalyst - keto ester - cyclization - furan - pyrrole

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