The absolute configuration of simple aliphatic alcohols through a chemical/computational approach: triarylether derivatives of (+)-endo-2-norborneol as a case study

The reliable determination of the absolute configuration of (+)-endo-2-norborneol 1, chosen as a representative case of simple aliphatic UV-vis transparent alcohols, was obtained by transforming this compound in its 1-naphthyl-diphenylmethyl ether 5 whose ECD spectrum displays several, low-lying, intense Cotton effects, which can be satisfactorily simulated in position, sign, and intensity by TDDFT/B3LYP/6-31G* calculations. This result represents a possible, general, new approach to the absolute configuration of aliphatic alcohols. © 2009 Elsevier Ltd. All rights reserved.