Issue 73, 2016

The synthesis of substituted phosphathiahelicenes via regioselective bromination of a preformed helical scaffold: a new approach to modular ligands for enantioselective gold-catalysis

Abstract

Substituted phosphathiahelicenes have been prepared via a straightforward two-step procedure involving the regioselective bromination of a preformed helical scaffold, followed by palladium catalyzed coupling reactions. The new helicenes have been used as ligands in gold(I)-catalyzed [4+2] cyclizations of 1,6-enynes. The resulting dihydro-cyclopenta[b]naphthalene derivative was obtained in excellent yields and with up to 91% ee.

Graphical abstract: The synthesis of substituted phosphathiahelicenes via regioselective bromination of a preformed helical scaffold: a new approach to modular ligands for enantioselective gold-catalysis

Supplementary files

Article information

Article type
Communication
Submitted
07 Jun 2016
Accepted
06 Aug 2016
First published
18 Aug 2016

Chem. Commun., 2016,52, 10984-10987

The synthesis of substituted phosphathiahelicenes via regioselective bromination of a preformed helical scaffold: a new approach to modular ligands for enantioselective gold-catalysis

P. Aillard, D. Dova, V. Magné, P. Retailleau, S. Cauteruccio, E. Licandro, A. Voituriez and A. Marinetti, Chem. Commun., 2016, 52, 10984 DOI: 10.1039/C6CC04765C

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