New chiral bidentate ligands containing thiazolyl and pyridyl donors for copper-catalyzed asymmetric allylic oxidation of cyclohexene

Research output: Journal Publications and Reviews (RGC: 21, 22, 62)21_Publication in refereed journalpeer-review

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Author(s)

  • Pang-Fei Teng
  • Chui-Shan Tsang
  • Ho-Lun Yeung
  • Wing-Leung Wong
  • Ian D. Williams

Detail(s)

Original languageEnglish
Pages (from-to)2237-2244
Journal / PublicationJournal of Organometallic Chemistry
Volume691
Issue number10
Publication statusPublished - 1 May 2006

Abstract

Chiral bidentate ligands 1-3, which contain a combination of thiazolyl and pyridyl donors units, were prepared. The syntheses are facile and being based on Kröhnke condensation of a pinene derivative to form the pyridine ring. Modification at the 8-position of the tetrahydroquinoline ring can be carried out by alkylation reaction with 2a and 3a but not 1a. The structure of a copper(II) perchlorate complex of 1a was characterized with X-ray crystallography, which reveals the binding of the pyridyl-thiazole as a N-N donors at the copper center. The copper(I) thiazolyl-pyridine complexes prepared in situ are active catalysts in the enantioselective allylic oxidation of cyclohexene using tert-butyl perbenzoate as the oxidant. The isolated yields of the allylic benzoate were up to 98%, and enantioselectivity was up to 62% e.e. © 2005 Elsevier B.V. All rights reserved.

Research Area(s)

  • Allylic, Asymmetric, Copper, Oxidation, Pyridyl, Thiazolyl

Citation Format(s)

New chiral bidentate ligands containing thiazolyl and pyridyl donors for copper-catalyzed asymmetric allylic oxidation of cyclohexene. / Teng, Pang-Fei; Tsang, Chui-Shan; Yeung, Ho-Lun et al.

In: Journal of Organometallic Chemistry, Vol. 691, No. 10, 01.05.2006, p. 2237-2244.

Research output: Journal Publications and Reviews (RGC: 21, 22, 62)21_Publication in refereed journalpeer-review