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Issue 52, 2017
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Enantioselective gold(i)-catalyzed rearrangement of cyclopropyl-substituted 1,6-enynes into 2-oxocyclobutyl-cyclopentanes

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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

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Article information


Submitted
26 Apr 2017
Accepted
05 Jun 2017
First published
14 Jun 2017

Chem. Commun., 2017,53, 7026-7029
Article type
Communication

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

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