Resolution of Thiele’s acid

Resolution of Thiele’s acid

Jun Chen,^a XuXin Sun,^a Allen G. Oliver,^b Jeremy E. Wulff^a

^aDepartment of Chemistry, University of Victoria, P.O. Box 3065 STN CSC, Victoria, BC V8W 3V6, Canada.

^bMolecular Structure Facility, Department of Chemistry and Biochemistry, University of Notre Dame, 251 Nieuwland Science Hall, Notre Dame, IN 46556, USA.

Corresponding author: Jeremy E. Wulff (e-mail: wulff@uvic.ca).

ABSTRACT

Thiele’s acid has been resolved for the first time by diastereomeric salt formation with brucine. Determination of absolute stereochemistry was accomplished by X-ray crystallography of the corresponding diester. We anticipate that access to optically resolved Thiele’s acid will stimulate its use in a diverse range of applications requiring chiral molecular clefts.

Canadian Journal of Chemistry, 2017, 95(3): 234-238, 10.1139/cjc-2016-0125

 

(–)-Thiele’s ester 2a as a white solid (200 mg, 81%). Spectral data were consistent with the racemic compound that has been described previously in the literature.5 [α]D 25 = –216 deg mL dm-1 g-1 (c = 0.25, ethanol solution). MP = 87–89 °C.

CCDC 1469300 contains the supplementary crystallographic data for compound (–)-2a. These data are available from the Cambridge Crystallographic Data Centre.

 

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