Fischer型カルベン錯体を用いる有機合成
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概要
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The addition reaction of organolithium or Grignard reagents to silyl-substituted Fischer-type carbene complex gives either (<I>E</I>) - or (<I>Z</I>) -vinylsilanes with high selectivities depending on the reaction conditions.<BR>A new type of propargyl metallic species is generated by the addition reaction of alkynyllithiums with Fischer-type carbene complexes. These species act as regiochemically well-behaved propargyl metallic species and react with various electrophiles to give five-membered heterocyclic compounds. This reaction was applied to a concise enantioselective total synthesis of (-) -PI-091.<BR>Variable temperature NMR studies of the reaction of the propargyl tungsten species with electrophiles revealed that 1, 2-migration of pentacarbonyltungsten occurs to generate a vinyl metallic species. Highly efficient method was developed for the preparation of a variety of synthetically useful, fully substituted five-membered heterocyclic compounds by the iodine-oxidation of the intermediates produced from Fischer-type carbene complexes, alkynes, and various carbon electrophiles.
- 社団法人 有機合成化学協会の論文
- 1998-05-01