85323-06-4Relevant articles and documents
Chemical Synthesis and Optical Purity Determination of Optically Active 1,2-Epoxyindan and Alcohol Products which are also derived from Mammalian or Microbial Metabolism of Indene or Indanones
Boyd, Derek,Sharma, Narain D.,Smith, Alistair E.
, p. 2767 - 2770 (2007/10/02)
(+)-trans-2-Bromo-1-hydroxyindan (5) has been resolved into its enantiomers by preparative h.p.l.c. or fractional crystallization of the bromo-menthyloxy-acetoxydiastereoisomers (6a) and (6b).The bromohydrin (5) or bromo-esters (6a, 6b and 7) have in turn been converted into (-)-(1R,2S)-1,2-epoxyindan (2), (-)-(1R,2R)-trans-1-acetoxy-2-bromoindan (7), (+)-(1S)-indanol (8), (-)-(1R,2R)-trans-indan-1,2-diol (3), and (-)-(1S,2R)-cis-indan-1,2-diol (4).The optical purity of the alcohol products (3), (4), and (8) was determined by n.m.r. and h.p.l.c. analysis of their 2-methoxy-2-phenyl-2-trifluoromethylacetates.The previously unknown optical purity of the chiral alcohols (3), (4), (5), and (8), which had been isolated in earlier mammalian and microbial metabolism studies, has also been deduced.