Microscale determination of the absolute configuration of alpha-aryl-substituted alcohols by the CD exciton chirality method
The absolute configurations of a broad spectrum of aryl alcohols 1 have been determined for the first time by the CD exciton chirality method. The configurational assignment is additionally verified by computer modeling and lipase-catalyzed acetylation of the racemic alcohols. The CD-spectroscopic data have revealed that the S enantiomers of the benzoate derivatives 2 display a positive first Cotton effect and the R enantiomers a negative one at around 228 nm. Thus, the sense of the first Cotton effect of the benzoate derivative 2 allows a reliable assignment of the absolute configuration of the corresponding alcohol 1.
Adam
W
Contribution from the Institutes of Organic Chemistry and Food Chemistry, University of Wurzburg, Am Hubland, D-97074 Wurzburg, Germany.
Lukacs
Z
Viebach
K
Humpf
HU
Saha-Moller
CR
Schreier
P