Asymmetric desymmetrization of 2,2',6,6'-tetrahydroxybiphenyl through annulation with enantiomerically pure bis(mesylate)
[formula: see text] 2,2',6,6'-Tetrahydroxybiphenyl undergoes a facile annulation reaction with bis(mesylate) derived from (S)-1,2-propanediol in the presence of Cs2CO3 to give the corresponding asymmetric desymmetrization product of S axial chirality with exclusive diastereoselectivity. The desymmetrization product can be utilized as a versatile chiral building block in asymmetric synthesis of axially chiral 6,6'-disubstituted 2,2'-biphenyldiols.
Harada
T
Department of Chemistry, Kyoto Institute of Technology, Japan. harada@chem.kit.ac.jp
Tuyet
TM
Oku
A