Functionalized iminium salt systems for catalytic asymmetric epoxidation

P. C. B. Bulman Page; G. A. Rassias; D. Barros; A. Ardakani; B. Buckley; D. Bethell; T. A. D. Smith; A. M. Z. Slawin

doi:10.1021/jo010258n

Functionalized iminium salt systems for catalytic asymmetric epoxidation

P. C. B. Bulman Page, G. A. Rassias, D. Barros, A. Ardakani, B. Buckley, D. Bethell, T. A. D. Smith, A. M. Z. Slawin

Chemistry of Materials and Catalysis

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

86 Citations (Scopus)

Abstract

A range of dihydroisoquinolinium salts containing alcohol, ether, and acetal functionalities in the nitrogen substituent has been prepared and tested as asymmetric epoxidation catalysts, providing ee's of up to ca. 60%.

Original language	English
Pages (from-to)	6926-6931
Number of pages	6
Journal	Journal of Organic Chemistry
Volume	66
Issue number	21
DOIs	https://doi.org/10.1021/jo010258n
Publication status	Published - 2001

Keywords

HYDROGEN-PEROXIDE
ALKENE EPOXIDATION
SYSTEM
SYNTHETIC ENZYMES
HIGHLY ENANTIOSELECTIVE EPOXIDATION
CHIRAL OXAZIRIDINIUM SALT
EFFICIENT EPOXIDATION
N-SULFONYLOXAZIRIDINES
OXYGEN-TRANSFER
UNFUNCTIONALIZED OLEFINS
TRIPHASE

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10.1021/jo010258n

Cite this

@article{345a603ff44e4c66b278118f480819a1,

title = "Functionalized iminium salt systems for catalytic asymmetric epoxidation",

abstract = "A range of dihydroisoquinolinium salts containing alcohol, ether, and acetal functionalities in the nitrogen substituent has been prepared and tested as asymmetric epoxidation catalysts, providing ee's of up to ca. 60%.",

keywords = "HYDROGEN-PEROXIDE, ALKENE EPOXIDATION, SYSTEM, SYNTHETIC ENZYMES, HIGHLY ENANTIOSELECTIVE EPOXIDATION, CHIRAL OXAZIRIDINIUM SALT, EFFICIENT EPOXIDATION, N-SULFONYLOXAZIRIDINES, OXYGEN-TRANSFER, UNFUNCTIONALIZED OLEFINS, TRIPHASE",

author = "{Bulman Page}, {P. C. B.} and Rassias, {G. A.} and D. Barros and A. Ardakani and B. Buckley and D. Bethell and Smith, {T. A. D.} and Slawin, {A. M. Z.}",

year = "2001",

doi = "10.1021/jo010258n",

language = "English",

volume = "66",

pages = "6926--6931",

journal = "Journal of Organic Chemistry",

issn = "0022-3263",

publisher = "American Chemical Society",

number = "21",

}

TY - JOUR

T1 - Functionalized iminium salt systems for catalytic asymmetric epoxidation

AU - Bulman Page, P. C. B.

AU - Rassias, G. A.

AU - Barros, D.

AU - Ardakani, A.

AU - Buckley, B.

AU - Bethell, D.

AU - Smith, T. A. D.

AU - Slawin, A. M. Z.

PY - 2001

Y1 - 2001

N2 - A range of dihydroisoquinolinium salts containing alcohol, ether, and acetal functionalities in the nitrogen substituent has been prepared and tested as asymmetric epoxidation catalysts, providing ee's of up to ca. 60%.

AB - A range of dihydroisoquinolinium salts containing alcohol, ether, and acetal functionalities in the nitrogen substituent has been prepared and tested as asymmetric epoxidation catalysts, providing ee's of up to ca. 60%.

KW - HYDROGEN-PEROXIDE

KW - ALKENE EPOXIDATION

KW - SYSTEM

KW - SYNTHETIC ENZYMES

KW - HIGHLY ENANTIOSELECTIVE EPOXIDATION

KW - CHIRAL OXAZIRIDINIUM SALT

KW - EFFICIENT EPOXIDATION

KW - N-SULFONYLOXAZIRIDINES

KW - OXYGEN-TRANSFER

KW - UNFUNCTIONALIZED OLEFINS

KW - TRIPHASE

U2 - 10.1021/jo010258n

DO - 10.1021/jo010258n

M3 - Article

VL - 66

SP - 6926

EP - 6931

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

SN - 0022-3263

IS - 21

ER -