Cycloisomerization Promoted by the Combination of a Ruthenium–Carbene Catalyst and Trimethylsilyl Vinyl Ether, and its Application in The Synthesis of Heterocyclic Compounds: 3-Methylene-2,3-dihydroindoles and 3-Methylene-2,3-dihydrobenzofurans

✍ Scribed by Yukiyoshi Terada; Mitsuhiro Arisawa; Atsushi Nishida

• Publisher: John Wiley and Sons
• Year: 2004
• Tongue: English
• Weight: 246 KB
• Volume: 116
• Category: Article
• ISSN: 0044-8249
• DOI: 10.1002/ange.200454157

✦ Synopsis

Transition-metal-catalyzed cyclization of a,w-dienes is an efficient method for the construction of carbo-and heterocycles. One particularly interesting cyclization is olefin metathesis, [1] in which significant progress was made after the development of well-defined ruthenium-carbene catalysts, such as A and B (Scheme 1). In particular, the commercially available ruthenium-carbene catalyst B has shown enhanced activity in ring-closing metathesis (RCM), ring-opening metathesis polymerization (ROMP), and cross metathesis (CM). [1c, 2] On the other hand, the nonmetathetic behaviors of ruthenium-carbene catalysts have been demonstrated in recent studies of olefin metatheses. [3] When a substrate cannot give a product by metathesis, nonmetathetic reactions, such as the Kharasch addition, [4] olefin isomerization, [5] and hydro-