Some recent applications of Fischer carbenemetal complexes in organic synthesis

Yao Ting Wu, Takuya Kurahashi, Armin De Meijere

研究成果: Article同行評審

47 引文 斯高帕斯(Scopus)

摘要

{[2-(Dialkylamino)ethenyl]ethoxycarbene}chromium complexes 4 have been made available from lithiated terminal alkynes, hexacarbonylchromium, triethyloxonium tetrafluoroborate and secondary amines in a one-pot operation, in good to excellent yields. Reactions of these complexes with alkynes afford 5-dialkylamino-3-ethoxycyclopentadienes 8 with excellent chemoselectivity. From cyclopentadienes of type 8, angular and linear triquinanes, di- and triannelated benzene derivatives 24/25, steroid-like skeletons 30/31, and hexacycles 32/33 can be obtained with great facility. In addition, otherwise not easily accessible cyclopenta[b]pyrans 42/43 and novel spiro[4.4]nonatrienes 52/53 can be prepared in single operational steps from complexes 4 and terminal alkynes via [3 + 2 + 2 + 1] and [3 + 2 + 2 + 2] cocyclizations incorporating two and three alkyne units, respectively. Upon heating simple Fischer carbene complexes of type 2 with methylenecyclopropanes 64, cyclopentenones 65 are formed by formal [4 + 1] cycloadditions. New carbenemetal complexes which have different chemical reactivities can be formed in situ by transmetallation from the corresponding carbenechromium complexes. Various cyclopentenone, cyclopentene and cycloheptanone derivatives are easily accessible from these new carbenemetal (nickel and rhodium) complexes and an alkyne or an allene.

原文English
頁(從 - 到)5900-5911
頁數12
期刊Journal of Organometallic Chemistry
690
發行號24-25
DOIs
出版狀態Published - 2005 十二月 1

All Science Journal Classification (ASJC) codes

  • 生物化學
  • 物理與理論化學
  • 有機化學
  • 無機化學
  • 材料化學

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