ChemInform Abstract: Asymmetric Synthesis of Axially Chiral Biaryls via Desymmetrization of 2,2′,6,6′-Tetrahydroxybiphenyl Using 1,4-Di-O-benzyl-L-threitol as a Chiral Template.
Abstract
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ChemInform Abstract
(S)-Axially chiral biphenyl (V), prepared from prochiral tetrol (I) using desymmetrization with threitol (II) under Mitsunobu conditions, is proved to be a versatile intermediate for the synthesis of chiral bridged biphenyls (VIII). It is also demonstrated that palladium-catalyzed coupling of bis(triflate) (IX) with organozinc compounds can be used for synthesis of dialkyl- and diphenylbiphenyls (XII) and derivatives (XVI) and (XVIII).
