A new one-step strategy for the stereochemical assignment of acyclic 2- and 3-sulfanyl-1-alkanols using the CD exciton chirality method

Article abstract of DOI:10.1021/jo010768h

A new one-step strategy is described for the stereochemical assignment of acyclic 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 determination of the stereochemistry from a single CD measurement. The usefulness of the new method is demonstrated using synthesized optically pure 3-sulfanyl-1-hexanols and 2-sulfanyl-1-hexanols as model compounds. The developed microscale method is also useful for the stereochemical assignment of 1,2- and 1,3-diols. To our knowledge this is the first application of the CD exciton chirality method to acyclic 2- and 3-sulfanyl-1-alkanols.