Gold(I) catalyzed isomerization of 5-en-2-yn-1-yl acetates: An efficient access to acetoxy bicyclo[3.1.0]hexenes and 2-cycloalken-1-ones

Andrea Buzas 1 Fabien Gagosz 1, *
* Corresponding author
1 DCSO - Laboratoire de synthèse organique
Abstract : The gold(I) catalyzed rearrangement of 5-en-2-yn-1-yl acetates into functionalized acetoxy bicyclo[3.1.0]hexenes is described. The mild reaction conditions employed allow the efficient and rapid synthesis of a variety of such bicyclic compounds via a sequence of two gold(I)-catalyzed isomerization steps. Acetoxy bicyclo[3.1.0]hexenes products can be further transformed to 2-cycloalkenones by simple methanolysis. Copyright © 2006 American Chemical Society.
Document type :
Journal articles
Complete list of metadatas
https://hal-polytechnique.archives-ouvertes.fr/hal-00951310
Contributor : Denis Roura <>
Submitted on : Monday, March 3, 2014 - 3:08:12 PM
Last modification on : Thursday, February 7, 2019 - 5:19:48 PM

Links full text

istex

Identifiers

Collections

CNRS | X-DCSO | X | PARISTECH | INC-CNRS | X-DEP-CHIM

Citation

Andrea Buzas, Fabien Gagosz. Gold(I) catalyzed isomerization of 5-en-2-yn-1-yl acetates: An efficient access to acetoxy bicyclo[3.1.0]hexenes and 2-cycloalken-1-ones. Journal of the American Chemical Society, American Chemical Society, 2006, 128 (39), pp.12614-12615. ⟨10.1021/ja064223m⟩. ⟨hal-00951310⟩

Export

BibTeX TEI DC DCterms EndNote

Share

Metrics

Record views

167

Contact

Informations

CCSD