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.