Template-controlled synthesis of chiral cyclohexylhemicucurbit[8]uril

E. Prigorchenko; M. Öeren; S. Kaabel; M. Fomitšenko; I. Reile; I. Järving; T. Tamm; F. Topić; K. Rissanen; R. Aav

doi:10.1039/C5CC04101E

Template-controlled synthesis of chiral cyclohexylhemicucurbit[8]uril†

E. Prigorchenko,^a M. Öeren,^a S. Kaabel,^a M. Fomitšenko,^a I. Reile,^b I. Järving,^a T. Tamm,^a F. Topić,^c K. Rissanen^c and R. Aav*^a

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^a Department of Chemistry, Tallinn University of Technology, Akadeemia tee 15, 12618 Tallinn, Estonia
E-mail: riina.aav@ttu.ee

^b National Institute of Chemical Physics and Biophysics, Akadeemia tee 23, 12618 Tallinn, Estonia

^c University of Jyvaskyla, Department of Chemistry, Nanoscience Center, P.O. Box. 35, FI-40014 Jyvaskyla, Finland

Abstract

Enantiomerically pure cyclohexylhemicucurbit[8]uril (cycHC[8]), possessing a barrel-shaped cavity, has been prepared in high yield on a gram scale from either (R,R,N,N′)-cyclohex-1,2-diylurea and formaldehyde or cycHC[6]. In either case, a dynamic covalent library is first generated from which the desired cycHC can be amplified using a suitable anion template.

Chemical Communications

Template-controlled synthesis of chiral cyclohexylhemicucurbit[8]uril†

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Template-controlled synthesis of chiral cyclohexylhemicucurbit[8]uril

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