Towards the enantioselective synthesis of axially chiral cyclic bis(bibenzyls) through sulfoxide-controlled diastereoselective Suzuki coupling

Natural macrocyclic bis(bibenzyls) exhibiting configurationally stable axially chiral biaryls are of high interest from a structural as well as from a synthetic point of view. An enantiopure sulfinyl auxiliary controlling an atropo-diastereoselective biaryl Suzuki coupling reaction has been investigated and promising results for the preparation of the biaryl moiety of cyclic bis(bibenzyls) like isoplagiochins C or D have been obtained. Furthermore, models explaining the stereoselectivity during transition state, and substitution effects including double stereo-differentiation, were discussed. (C) 2016 Elsevier Ltd. All rights reserved.