Jump to main content
Jump to site search

Issue 52, 2017
Previous Article Next Article

Enantioselective gold(I)-catalyzed rearrangement of cyclopropyl-substituted 1,6-enynes into 2-oxocyclobutyl-cyclopentanes

Author affiliations

Abstract

A gold(I)-catalyzed cycloisomerization/ring expansion sequence allows the highly enantioselective synthesis of 2-oxocyclobutylcyclopentane derivatives from cyclopropyl-substituted enynes. The bimetallic [(R)-MeO-DTBM-BIPHEP-(AuCl)2] complex was found to be the best precatalyst, affording the desired cyclobutanones in high yields and enantioselectivities (up to 99% ee). The usefulness of the method was further demonstrated by preparing the tricyclic core scaffold of russujaponol D.

Graphical abstract: Enantioselective gold(i)-catalyzed rearrangement of cyclopropyl-substituted 1,6-enynes into 2-oxocyclobutyl-cyclopentanes

Back to tab navigation

Supplementary files

Publication details

The article was received on 26 Apr 2017, accepted on 05 Jun 2017 and first published on 14 Jun 2017


Article type: Communication
DOI: 10.1039/C7CC03234J
Citation: Chem. Commun., 2017,53, 7026-7029
  •   Request permissions

    Enantioselective gold(I)-catalyzed rearrangement of cyclopropyl-substituted 1,6-enynes into 2-oxocyclobutyl-cyclopentanes

    Z. Wu, D. Lebœuf, P. Retailleau, V. Gandon, A. Marinetti and A. Voituriez, Chem. Commun., 2017, 53, 7026
    DOI: 10.1039/C7CC03234J

Search articles by author

Spotlight

Advertisements