AXIALLY CHIRAL 1,1'-BINAPHTHYLS WITH NON-IDENTICAL GROUPS IN 2,2'-POSITIONS. SYNTHESIS OF THE ENANTIOMERICALLY PURE 2-HYDROXY-2'-THIOL AND SUBSTITUTED 2-AMINO-2'-THIOLS

Abstract Enantiomerically pure hydroxy thiol (S)-(+)- 6 , amino thiol (S)-(+)- 12 , and N , N -dimethylamino thiol (S)-(−)- 16 have been synthesized from BINOL (S)-(−)- 1 and the amino alcohol (S)-(−)- 7 , respectively, via the Newman-Kwart rearrangement of the corresponding thiocarbamoyl derivatives (S)-(−)- 2 , (S)-(−)- 10 , and (S)-(−)- 14 . Configurational stability of the binaphthyl unit has been observed.