A Nonenzymatic Kinetic Resolution of (±)-trans-2-Arylcyclohexanols via Esterification Using Polymer-Supported DCC, DMAP, and 3β-Acetoxyetienic Acid

Abstract

A nonenzymatic kinetic resolution of (±)-trans-2-arylcyclohexanols was carried out by esterification using polymer-supported N,N′-dicyclohexylcarbodiimide (DCC), dimethylaminopyridine (DMAP), and 3β-acetoxyetienic acid. The efficiency of the kinetic resolution was comparable to the enzymatic method when arylcyclohexanols bearing a condensed-aromatic ring were used.

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GRAPHICAL ABSTRACT

Keywords:

• Esterification
• kinetic resolution
• nonenzymatic
• polymer-supported DCC

ACKNOWLEDGMENTS

This research was partially supported by the Ministry of Education, Science, Sports, and Culture, Grant-in-Aid for Scientific Research (C), 23580154, and the Fund for Agriomics Project.

Notes

^a The de value was determined by ¹H NMR spectra.

^b The ee value was determined by HPLC analysis (CHIRAL CEL OD, hexane/ ⁱ PrOH = 95/5, flow rate; 1.0 ml/min.).

^c s values were calculated according to Kagan's method. See: Ref. 10. s = ln[(1 − C)(1 − ee)] / ln[(1 − C)(1 +ee)], C = conversion.

^d The reaction was conducted for 20 h.

^e The reaction was conducted for 30 h.

^a The de was detennined by ¹H NMR.

^b The ee was determined by HPLC analysis (la, lb: CHIRAL CEL OD, hexane/ ⁱ PrOH = 95/5, flow rate: 1.0 ml/min, lc: CHIRAL CEL OD, hexane/ ⁱ PrOH = 99/1, flow rate: 0.5 ml/min, ld–f: CHIRAL CEL OJ, hexane/PrOH = 99/1, flow rate: 1.0 ml/min).

^c The s was calculated according to Kagan's method. See: Ref. 10. s  = ln[(l − C)(l − ee)] / ln[(l − C) (1 + ee)], C = conversion.