Kinetic Resolution in Asymmetric Epoxidation using Iminium Salt Catalysis

Philip C. Bulman Page; Louise F. Appleby; Yohan Chan; David P. Day; Benjamin R. Buckley; Alexandra M. Z. Slawin; Steven M. Allin; Michael J. McKenzie

doi:10.1021/jo401345m

Kinetic Resolution in Asymmetric Epoxidation using Iminium Salt Catalysis

Philip C. Bulman Page^*, Louise F. Appleby, Yohan Chan, David P. Day, Benjamin R. Buckley, Alexandra M. Z. Slawin, Steven M. Allin, Michael J. McKenzie

^*Corresponding author for this work

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

Abstract

The first reported examples of kinetic resolution in epoxidation reactions using iminium salt catalysis are described, providing up to 99% ee in the epoxidation of racemic cis-chromenes.

Original language	English
Pages (from-to)	8074-8082
Number of pages	9
Journal	The Journal of Organic Chemistry
Volume	78
Issue number	16
DOIs	https://doi.org/10.1021/jo401345m
Publication status	Published - 16 Aug 2013

Keywords

ENANTIOSELECTIVE OLEFIN EPOXIDATION
OXAZIRIDINIUM-MEDIATED EPOXIDATION
CHIRAL KETONE
UNFUNCTIONALIZED OLEFINS
HYDROGEN-PEROXIDE
HIGHLY EFFICIENT
ALLYLIC ALCOHOLS
STEREOSPECIFIC SYNTHESIS
STOICHIOMETRIC OXIDANT
ALKENE EPOXIDATION

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@article{77cfc518bda44b7fa5ea587ca639a2be,

title = "Kinetic Resolution in Asymmetric Epoxidation using Iminium Salt Catalysis",

abstract = "The first reported examples of kinetic resolution in epoxidation reactions using iminium salt catalysis are described, providing up to 99% ee in the epoxidation of racemic cis-chromenes.",

keywords = "ENANTIOSELECTIVE OLEFIN EPOXIDATION, OXAZIRIDINIUM-MEDIATED EPOXIDATION, CHIRAL KETONE, UNFUNCTIONALIZED OLEFINS, HYDROGEN-PEROXIDE, HIGHLY EFFICIENT, ALLYLIC ALCOHOLS, STEREOSPECIFIC SYNTHESIS, STOICHIOMETRIC OXIDANT, ALKENE EPOXIDATION",

author = "Page, {Philip C. Bulman} and Appleby, {Louise F.} and Yohan Chan and Day, {David P.} and Buckley, {Benjamin R.} and Slawin, {Alexandra M. Z.} and Allin, {Steven M.} and McKenzie, {Michael J.}",

year = "2013",

month = aug,

day = "16",

doi = "10.1021/jo401345m",

language = "English",

volume = "78",

pages = "8074--8082",

journal = "The Journal of Organic Chemistry",

issn = "0022-3263",

publisher = "American Chemical Society (ACS)",

number = "16",

}

TY - JOUR

T1 - Kinetic Resolution in Asymmetric Epoxidation using Iminium Salt Catalysis

AU - Page, Philip C. Bulman

AU - Appleby, Louise F.

AU - Chan, Yohan

AU - Day, David P.

AU - Buckley, Benjamin R.

AU - Slawin, Alexandra M. Z.

AU - Allin, Steven M.

AU - McKenzie, Michael J.

PY - 2013/8/16

Y1 - 2013/8/16

N2 - The first reported examples of kinetic resolution in epoxidation reactions using iminium salt catalysis are described, providing up to 99% ee in the epoxidation of racemic cis-chromenes.

AB - The first reported examples of kinetic resolution in epoxidation reactions using iminium salt catalysis are described, providing up to 99% ee in the epoxidation of racemic cis-chromenes.

KW - ENANTIOSELECTIVE OLEFIN EPOXIDATION

KW - OXAZIRIDINIUM-MEDIATED EPOXIDATION

KW - CHIRAL KETONE

KW - UNFUNCTIONALIZED OLEFINS

KW - HYDROGEN-PEROXIDE

KW - HIGHLY EFFICIENT

KW - ALLYLIC ALCOHOLS

KW - STEREOSPECIFIC SYNTHESIS

KW - STOICHIOMETRIC OXIDANT

KW - ALKENE EPOXIDATION

U2 - 10.1021/jo401345m

DO - 10.1021/jo401345m

M3 - Article

SN - 0022-3263

VL - 78

SP - 8074

EP - 8082

JO - The Journal of Organic Chemistry

JF - The Journal of Organic Chemistry

IS - 16

ER -

Kinetic Resolution in Asymmetric Epoxidation using Iminium Salt Catalysis

Abstract

Keywords

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