Asymmetric organocatalysis of epoxidation by iminium salts under non-aqueous conditions

P. C. B. Bulman Page; B. R. Buckley; D. Barros; A. J. Blacker; B. A. Marples; M. R. J. Elsegood

doi:10.1016/j.tet.2007.04.066

Asymmetric organocatalysis of epoxidation by iminium salts under non-aqueous conditions

P. C. B. Bulman Page, B. R. Buckley, D. Barros, A. J. Blacker, B. A. Marples, M. R. J. Elsegood

Research output: Contribution to journal › Article › peer-review

33 Citations (Scopus)

Abstract

Three iminium salts have been tested as catalysts for the asymmetric epoxidation of simple alkenes under non-aqueous conditions in various solvents, at varying temperatures, employing tetraphenylphosphonium monoperoxybisulfate (TPPP) as the stoichiometric oxidant. Enantiomeric excesses of up to 89% have been observed. (c) 2007 Elsevier Ltd. All rights reserved.

Original language	English
Pages (from-to)	5386-5393
Number of pages	8
Journal	Tetrahedron
Volume	63
Issue number	25
DOIs	https://doi.org/10.1016/j.tet.2007.04.066
Publication status	Published - 2007

Keywords

CATALYSTS
ENANTIOSELECTIVE OLEFIN EPOXIDATION
ALKENE
UNSATURATED OXAZIRIDINES
OXONE(R)
MECHANISM
CHIRAL OXAZIRIDINIUM SALT
OXIDATION
OXYGEN-TRANSFER
EPOXIDATION
INTRAMOLECULAR EPOXIDATION

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10.1016/j.tet.2007.04.066

Cite this

@article{715af6aceafc40388d34ba1cdee3688c,

title = "Asymmetric organocatalysis of epoxidation by iminium salts under non-aqueous conditions",

abstract = "Three iminium salts have been tested as catalysts for the asymmetric epoxidation of simple alkenes under non-aqueous conditions in various solvents, at varying temperatures, employing tetraphenylphosphonium monoperoxybisulfate (TPPP) as the stoichiometric oxidant. Enantiomeric excesses of up to 89% have been observed. (c) 2007 Elsevier Ltd. All rights reserved.",

keywords = "CATALYSTS, ENANTIOSELECTIVE OLEFIN EPOXIDATION, ALKENE, UNSATURATED OXAZIRIDINES, OXONE(R), MECHANISM, CHIRAL OXAZIRIDINIUM SALT, OXIDATION, OXYGEN-TRANSFER, EPOXIDATION, INTRAMOLECULAR EPOXIDATION",

author = "{Bulman Page}, {P. C. B.} and Buckley, {B. R.} and D. Barros and Blacker, {A. J.} and Marples, {B. A.} and Elsegood, {M. R. J.}",

year = "2007",

doi = "10.1016/j.tet.2007.04.066",

language = "English",

volume = "63",

pages = "5386--5393",

journal = "Tetrahedron",

issn = "0040-4020",

publisher = "Elsevier",

number = "25",

}

TY - JOUR

T1 - Asymmetric organocatalysis of epoxidation by iminium salts under non-aqueous conditions

AU - Bulman Page, P. C. B.

AU - Buckley, B. R.

AU - Barros, D.

AU - Blacker, A. J.

AU - Marples, B. A.

AU - Elsegood, M. R. J.

PY - 2007

Y1 - 2007

N2 - Three iminium salts have been tested as catalysts for the asymmetric epoxidation of simple alkenes under non-aqueous conditions in various solvents, at varying temperatures, employing tetraphenylphosphonium monoperoxybisulfate (TPPP) as the stoichiometric oxidant. Enantiomeric excesses of up to 89% have been observed. (c) 2007 Elsevier Ltd. All rights reserved.

AB - Three iminium salts have been tested as catalysts for the asymmetric epoxidation of simple alkenes under non-aqueous conditions in various solvents, at varying temperatures, employing tetraphenylphosphonium monoperoxybisulfate (TPPP) as the stoichiometric oxidant. Enantiomeric excesses of up to 89% have been observed. (c) 2007 Elsevier Ltd. All rights reserved.

KW - CATALYSTS

KW - ENANTIOSELECTIVE OLEFIN EPOXIDATION

KW - ALKENE

KW - UNSATURATED OXAZIRIDINES

KW - OXONE(R)

KW - MECHANISM

KW - CHIRAL OXAZIRIDINIUM SALT

KW - OXIDATION

KW - OXYGEN-TRANSFER

KW - EPOXIDATION

KW - INTRAMOLECULAR EPOXIDATION

U2 - 10.1016/j.tet.2007.04.066

DO - 10.1016/j.tet.2007.04.066

M3 - Article

SN - 0040-4020

VL - 63

SP - 5386

EP - 5393

JO - Tetrahedron

JF - Tetrahedron

IS - 25

ER -