M. Melmer et al., OPTICALLY-ACTIVE AROMATIC SPIRANES .18. S YNTHESES OF OPTICALLY-ACTIVE 4,4'-DISUBSTITUTED 2,2'-SPIROBI-S-HYDRINDACENES .1., Monatshefte fuer Chemie, 126(8-9), 1995, pp. 933-943
All optically active title compounds were obtained from the 4,4'-diace
tyl-spiro compound 2; (+)- and (-)-2 were accessible by chromatography
on triacetyl cellulose in ethanol. The enantiomeric purities were est
ablished from chromatographic data. The chirality(-)-(2R) was deduced
for all new compounds on the basis of the CD spectra of (-)-2 and )-2,
2'-spirobi-(5,6,7,8-tetrahydrobenzo[f]indane). From the molar rotation
s of these 4,4'-disubstituted 2,2'-spirobiindanes (empirical) ligand p
arameters lambda were determined (using the so-called ''shortened appr
oach''). Generally, the values of lambda in these com pounds are highe
r than those of the analogous tetrahydrobenzoindane derivatives.