Chromium catalysed asymmetric alkene epoxidation. greater selectivity for an E-alkene versus its Z-isomer

Bousquet, Claudine; Gilheany, Declan G.

doi:10.1016/0040-4039(95)01577-5

Cited by 83 publications

(43 citation statements)

References 25 publications

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“…Here the mechanism is presumed to involve an electrophilic process, which is supported by the fact that only electron-rich alkenes are effectively epoxidized. In the case of trans-b-methylstyrene (376, Scheme 2.60), enantioselectivities of up to 86% are achieved [418]. Gilheany and coworkers [419] have observed high (>90%) enantioselectivities for trans-alkenes using stoichiometric chromium complexes, albeit with modest chemical yields, presumably resulting from the formation of a m-oxo Cr(IV) dimer in situ.…”

Section: (S)-313mentioning

confidence: 99%

Three‐Membered Heterocycles. Structure and Reactivity

Murphree

2011

Modern Heterocyclic Chemistry

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Section: (S)-313mentioning

confidence: 99%

Three‐Membered Heterocycles. Structure and Reactivity

Murphree

2011

Modern Heterocyclic Chemistry

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“…The oxidation of hydrocarbons using Schiff base complexes has been in field of academic and industrial interest to analyze the catalytic activity of various metal complexes [6][7][8][9][10]. The activity of these complexes varied with the type of ligands, coordination sites and metal ions.…”

Section: Introductionmentioning

confidence: 99%

Homogenous and Heterogeneous Catalytic Activity of Azo-Linked Schiff Base Complexes of Mn(II), Cu(II) and Co(II)

Lashanizadegan

Zareian

2011

Catal Lett

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Azo linked Schiff-base[L] complexes of Mn(II)(1), Cu(II)(2) and Co(II)(3) obtained by template method, in the reaction of 4-(benzeneazo) salicylaldehyde with 1,2-propanediamine in the present of metal acetate, respectively. Complexes are used as catalyst for oxidation of cyclohexene with tert-butylhydroperoxide (TBHP); oxidation of cyclohexene catalyzed by these complexes gave 2-cyclohexene-1-one and 2-cyclohexene-1-ol as major products. Conversion of cyclohexene achieved was 95-100% with (1), (2) and (3), with selectivity of 57, 92 and 100% for 2-cyclohexene-1-one, respectively. The encapsulated Cu(II) complex (Cu-NaY) catalyzes the oxidation of cyclohexene using TBHP as oxidant in good yield. (Cu-NaY) under optimized reaction condition gave three reaction products. A maximum of 100% conversion of cyclohexene has been achieved where selectivity of 2-cyclohexene-1-one was 83%.

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“…In recent years our group has been working on the development of epoxidation catalysts based on a chromium salen template [6,[8][9][10][11][12][13][14][15][16]. These show a contrasting selectivity pattern to their manganese analogues in that they allow the asymmetric epoxidation, with iodosylbenzene as stoichiometric oxidant, of E-1,2-disubstituted with high enantioselectivity (>90% ee with complex 2) [8,12].…”

Section: Introductionmentioning

confidence: 99%