Tetrahedron

New pinene-derived pyridines as bidentate chiral ligands

AV Malkov, AJP Stewart-Liddon, F Teplý, L Kobr…

Index: Malkov, Andrei V.; Stewart-Liddon, Angus J.P.; Teply, Filip; Kobr, Lukas; Muir, Kenneth W.; Haigh, David; Kocovsky, Pavel Tetrahedron, 2008 , vol. 64, # 18 p. 4011 - 4025

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Citation Number: 37

Abstract

A synthesis of new bidentate pyridines 8a–d, 9, and 10 has been developed, starting from triflate 14, readily available from β-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- ...