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  Platinum-Catalyzed Cycloisomerization Reactions of Enynes

Fürstner, A., Stelzer, F., & Szillat, H. (2001). Platinum-Catalyzed Cycloisomerization Reactions of Enynes. Journal of the American Chemical Society, 123(48), 11863-11869. doi:10.1021/ja0109343.

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Fürstner, Alois1, Author           
Stelzer, Frank1, Author           
Szillat, Hauke1, Author           
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1Research Department Fürstner, Max-Planck-Institut für Kohlenforschung, Max Planck Society, ou_1445584              

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 Abstract: PtCl2 constitutes an efficient and practical catalyst for a set of different atom economical rearrangement reactions of enynes. This includes (i) a formal enyne metathesis reaction delivering 1,3-dienes, (ii) the formation of polycyclic vinylcyclopropane derivatives, and (iii) an unprecedented O→C allyl shift reaction if unsaturated ethers are employed. Although these transformations produce significantly different structural motifs, they share a common mechanism comprising a cationic manifold triggered by the π-complexation of Pt(II) onto the alkyne unit of the substrates. Strong experimental support for the proposed mechanism comes from deuterium-labeling studies, a careful analysis of the product distribution pattern, and the fact that in some cases PtCl2 can be replaced by simple Lewis or Brønsted acids as the catalysts.

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Language(s): eng - English
 Dates: 2001-04-112001-11-072001-12-05
 Publication Status: Published in print
 Pages: 7
 Publishing info: -
 Table of Contents: -
 Rev. Type: Peer
 Identifiers: DOI: 10.1021/ja0109343
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Title: Journal of the American Chemical Society
  Other : J. Am. Chem. Soc.
  Abbreviation : JACS
Source Genre: Journal
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Publ. Info: American Chemical Society
Pages: 7 Volume / Issue: 123 (48) Sequence Number: - Start / End Page: 11863 - 11869 Identifier: ISSN: 0002-7863
CoNE: https://pure.mpg.de/cone/journals/resource/954925376870