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

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

88 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

SN - 0022-3263

VL - 66

SP - 6926

EP - 6931

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

IS - 21

ER -