Resolution of Thiele’s acid

Resolution of Thiele’s acid

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

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: ).

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

STR0.JPG

 

str1

(–)-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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