B. Weckerle et al., A new one-step strategy for the stereochemical assignment of acyclic 2-and3-sulfanyl-1-alkanols using the CD exciton chirality method, J ORG CHEM, 66(24), 2001, pp. 8160-8164
A new one-step strategy is described for the stereochemical assignment of a
cyclic 2- and 3-sulfanyl-1-alkanols using the CD exciton chirality method.
Using the 9-anthroate chromophore for the derivatization of both functional
groups, the resulting bisignate CD curves unequivocally allow the determin
ation of the stereochemistry from a single CD measurement. The usefulness o
f the new method is demonstrated using synthesized optically pure 3-sulfany
l-1-hexanols and 2-sulfanyl-1-hexanols as model compounds. The developed mi
croscale method is also useful for the stereochemical assignment of 1,2- an
d 1,3-diols. To our knowledge this is the first application of the CD excit
on chirality method to acyclic 2- and 3-sulfanyl-1-alkanols.