A New Catalytic Prins Cyclization Leading to Oxa- and Azacycles
2008; American Chemical Society; Volume: 11; Issue: 2 Linguagem: Inglês
10.1021/ol802593u
ISSN1523-7060
AutoresPedro O. Miranda, Rubén M. Carballo, Victor S. Martı́n, Juan I. Padrón,
Tópico(s)Cyclopropane Reaction Mechanisms
ResumoA new Prins cyclization process that builds up one carbon−carbon bond, one heteroatom-carbon bond, and one halogen-carbon bond, (in an oxa- and azacycle) relies on an iron catalyst system formed from Fe(acac)3 and trimethylsilyl halide. The method displays a broad substrate scope and is economical, environmentally friendly, and experimentally simple. This catalytic method permits the construction of chloro, bromo and iodo heterocycles, by the suitable combination of iron(III) source, the corresponding trimethylsilyl halide and the solvent, in high yields.
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