REMARKABLE REVERSAL OF THE NONLINEAR EFFECT IN THE CATALYTIC ENANTIOSELECTIVE ALLYLIC OXIDATION OF CYCLOHEXENE USING COPPER PROLINE COMPLEXES AND T-BUTYL HYDROPEROXIDE

Authors
ZONDERVAN C FERINGA BL
Citation
C. Zondervan et Bl. Feringa, REMARKABLE REVERSAL OF THE NONLINEAR EFFECT IN THE CATALYTIC ENANTIOSELECTIVE ALLYLIC OXIDATION OF CYCLOHEXENE USING COPPER PROLINE COMPLEXES AND T-BUTYL HYDROPEROXIDE, Tetrahedron : asymmetry, 7(7), 1996, pp. 1895-1898
Citations number
22
Categorie Soggetti
Chemistry Inorganic & Nuclear","Chemistry Inorganic & Nuclear","Chemistry Physical
Journal title
Tetrahedron : asymmetry → ACNP
ISSN journal
09574166
Volume
7
Issue
7
Year of publication
1996
Pages
1895 - 1898
Database
ISI
SICI code
0957-4166(1996)7:7<1895:RROTNE>2.0.ZU;2-S
Abstract
Several examples of efficient catalytic conversions of cyclohexene to optically active 2-cyclohexenyl propionate are reported using t-butyl hydroperoxide as oxidant. With the bis (S)-prolinato copper(II) comple x enantioselectivities up to 63% with good conversions were obtained. A negative non-linear ligand effect was observed. Addition of catalyti c amounts of anthraquinone resulted in a higher enantioselectivity as well as a reversal of the non-linear effect. Copyright (C) 1996 Elsevi er Science Ltd