Tetramethylnorbornadiene, a Versatile Alkene for Cyclopentenone Synthesis through Intermolecular Pauson鈥揔hand Reactions

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• 作者：Marc Rev茅s ; Agust铆 Lled贸 ; Yining Ji ; Emma Blasi ; Antoni Riera ; Xavier Verdaguer
• 刊名：Organic Letters
• 出版年：2012
• 出版时间：July 6, 2012
• 年：2012
• 卷：14
• 期：13
• 页码：3534-3537
• 全文大小：249K
• 年卷期：v.14,no.13(July 6, 2012)
• ISSN：1523-7052

文摘

1,2,3,4-Tetramethyl-bicyclo[2.2.1]hepta-2,5-diene (TMNBD, for tetramethylnorbornadiene) has been prepared and used successfully as an acetylene equivalent in the synthesis of substituted cyclopentenones. TMNBD is easily accessible on a multigram scale and displays excellent reactivity toward the intermolecular Pauson鈥揔hand reaction. Conjugate additions on the resulting tricyclic compounds proceed with exquisite diastereoselectivity. The retro-Diels鈥揂lder reaction of these TMNBD derivatives occurs under much smoother conditions than those required for its norbornadiene homologues.