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New pinene-derived pyridines as bidentate chiral ligands

Author(s): A. V. Malkov, A. J. P. Stewart-Liddon, F. Teply, L. Kobr, K. W. Muir, D. Haigh, P. Kocovsky

A synthesis of new bidentate pyridines 8a-d, 9, and 10 has been developed, starting from triflate 14, readily available from beta-pinene 11. A copper complex of the pyridine-oxazoline ligands 8a has been found to catalyze asymmetric allylic oxidation of cyclic olefins 36a-c with good conversion rates and acceptable enantioselectivity (<= 67% ee). The imidazolium salt 10 has been identified as a precursor of the corresponding N,N'-unsymmetrical N-heterocyclic carbene ligand, whose complex with palladium catalyzed the intramolecular amide enolate alpha-arylation leading to oxindole 45 in excellent yield but with low enantioselectivity. (c) 2008 Elsevier Ltd. All rights reserved.

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ISBN: 0040-4020
Publication Year: 2008
Periodical: Tetrahedron
Periodical Number: 18
Volume: 64
Pages: 4011-4025
Author Address: