Journal
TETRAHEDRON
Volume 72, Issue 34, Pages 5230-5237Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2015.12.052
Keywords
Natural product; Atropisomerism; Suzuki-Miyaura cross-coupling; Sulfoxide; Bis(bibenzyl) macrocycles
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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.
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