Issue 7, 2001

Studies on olefinepoxidation with t-BuOOH catalysed by dioxomolybdenum(VI) complexes of a novel chiral pyridyl alcoholate ligand

Abstract

The chiral dioxomolybdenum(VI) complexes [MoCl{(1R,2S,5S)-8-trimethylsilyloxy-1-(2-pyridyl)mentholato}(O)2(THF)] and [Mo{(1R,2S,5S)-8-trimethylsilyloxy-1-(2-pyridyl)mentholato}2(O)2] have been prepared in good yields by reaction of the solvent substituted complex [MoCl2O2(THF)2] with one or two equivalents of chiral 2′-pyridyl alcohol. The optically active aminoalcohol was obtained by reaction of 2-pyridyllithium with (−)-(2S,5S)-8-trimethylsilyloxymenthone. The complexes are active catalysts in the homogeneous epoxidation of cyclic and linear olefins, dienes and terpenes by t-BuOOH. They present remarkable activity and excellent product selectivity in cyclooctene epoxidation (cyclooctene oxide was obtained in quantitative yield). In the case of limonene, regioselectivity is high in favour of the epoxidation of the internal cyclic double bond. Ring opening activity was also observed for α-pinene oxide, producing campholenic aldehyde and epoxy campholenic aldehyde.

Article information

Article type
Paper
Submitted
19 Mar 2001
Accepted
27 Apr 2001
First published
08 Jun 2001

New J. Chem., 2001,25, 959-963

Studies on olefin epoxidation with t-BuOOH catalysed by dioxomolybdenum(VI) complexes of a novel chiral pyridyl alcoholate ligand

A. A. Valente, I. S. Gonçalves, A. D. Lopes, J. E. Rodríguez-Borges, M. Pillinger, C. C. Romão, J. Rocha and X. García-Mera, New J. Chem., 2001, 25, 959 DOI: 10.1039/B102523F

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