Synthesis, Table of Contents PAPER© Georg Thieme Verlag Stuttgart · New YorkGaCl3-Catalyzed α-Ethenylation Reaction of KetoneRyo Amemiya, Yoshio Nishimura, Masahiko Yamaguchi*Department of Organic Chemistry, Graduate School of Pharmaceutical Sciences, Tohoku University, Aoba, Sendai 980-8578, JapanFax: +81(22)2176811; e-Mail: yama@mail.pharm.tohoku.ac.jp; Recommend Article Abstract Buy Article(opens in new window) All articles of this category(opens in new window) Abstract In the presence of catalytic amounts of GaCl3 (10 mol%) and 2,6-di(t-butyl)-4-methylpyridine (10 mol%), five- or six-membered ring ketones possessing α,α′-disubstituents are ethenylated at the α-carbon with triethylsilylethyne at 180 °C. The roles of the base are to inhibit decomposition of the products and to promote protodegallation of the organogallium intermediates. Keywords catalytic reaction - α-ethenylation - GaCl3 - cyclic ketone - silylethyne Full Text References References <A NAME="RC01304SS-1">1</A> Millard AA. Rathke MW. J. Am. Chem. Soc. 1977, 99: 4833 <A NAME="RC01304SS-2">2</A> Chieffi A. Kamikawa K. Åhman J. Fox JM. Buchwald SL. Org. Lett. 2001, 3: 1897 <A NAME="RC01304SS-3">3</A> Seefelder M. Liebigs Ann. Chem. 1962, 652: 107 <A NAME="RC01304SS-4A">4a</A> Makosza M. Czyzewsky J. Jawdosiuk M. Org. Synth. 1976, 55: 99 <A NAME="RC01304SS-4B">4b</A> Makosza M. Tetrahedron Lett. 1966, 45: 5489 <A NAME="RC01304SS-5">5</A> Tzalis D. Knochel P. Angew. Chem. Int. Ed. 1999, 38: 1463 <A NAME="RC01304SS-6">6</A> Nakamura M. Endo K. Nakamura E. J. Am. Chem. Soc. 2003, 125: 13002 <A NAME="RC01304SS-7A">7a</A> Yamaguchi M. Tsukagoshi T. Arisawa M. J. Am. Chem. Soc. 1999, 121: 4074 <A NAME="RC01304SS-7B">7b</A> Arisawa M. Miyagawa C. Yamaguchi M. Synthesis 2002, 138 <A NAME="RC01304SS-8">8</A> Arisawa M. Akamatsu K. Yamaguchi M. Org. Lett. 2001, 3: 789 <A NAME="RC01304SS-9">9</A> Arisawa M. Miyagawa C. Yoshimura S. Kido Y. Yamaguchi M. Chem. Lett. 2001, 1080 <A NAME="RC01304SS-10">10</A> We reported a catalytic ethenylation reaction of phenols using SnCl4: Kobayashi K. Yamaguchi M. Org. Lett. 2001, 3: 241