New chiral binaphthalene-derived iminium salt organocatalysts for asymmetric epoxidation of alkenes

P. C. B. Bulman Page; M. M. Farah; B. R. Buckley; A. J. Blacker

doi:10.1021/jo070255w

New chiral binaphthalene-derived iminium salt organocatalysts for asymmetric epoxidation of alkenes

P. C. B. Bulman Page, M. M. Farah, B. R. Buckley, A. J. Blacker

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

47 Citations (Scopus)

Abstract

A series of binaphthalene-fused azepinium salts has been generated and used as organocatalysts in the asymmetric epoxidation of unfunctionalized alkenes, giving rise to ees of up to 84%.

Original language	English
Pages (from-to)	4424-4430
Number of pages	7
Journal	The Journal of Organic Chemistry
Volume	72
Issue number	12
DOIs	https://doi.org/10.1021/jo070255w
Publication status	Published - 2007

Keywords

CIS-OLEFINS
ENANTIOSELECTIVE OLEFIN EPOXIDATION
OXAZIRIDINIUM SALT
IN-SITU
OXONE
DIOXIRANE
TERMINAL OLEFINS
OXYGEN-TRANSFER
CINNAMIC ACID-DERIVATIVES
AMINE-CATALYZED EPOXIDATION

Access to Document

10.1021/jo070255w

Cite this

@article{6c36d21273754cfdbc5fff490feed22d,

title = "New chiral binaphthalene-derived iminium salt organocatalysts for asymmetric epoxidation of alkenes",

abstract = "A series of binaphthalene-fused azepinium salts has been generated and used as organocatalysts in the asymmetric epoxidation of unfunctionalized alkenes, giving rise to ees of up to 84%.",

keywords = "CIS-OLEFINS, ENANTIOSELECTIVE OLEFIN EPOXIDATION, OXAZIRIDINIUM SALT, IN-SITU, OXONE, DIOXIRANE, TERMINAL OLEFINS, OXYGEN-TRANSFER, CINNAMIC ACID-DERIVATIVES, AMINE-CATALYZED EPOXIDATION",

author = "{Bulman Page}, {P. C. B.} and Farah, {M. M.} and Buckley, {B. R.} and Blacker, {A. J.}",

year = "2007",

doi = "10.1021/jo070255w",

language = "English",

volume = "72",

pages = "4424--4430",

journal = "The Journal of Organic Chemistry",

issn = "0022-3263",

publisher = "American Chemical Society",

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T1 - New chiral binaphthalene-derived iminium salt organocatalysts for asymmetric epoxidation of alkenes

AU - Bulman Page, P. C. B.

AU - Farah, M. M.

AU - Buckley, B. R.

AU - Blacker, A. J.

PY - 2007

Y1 - 2007

N2 - A series of binaphthalene-fused azepinium salts has been generated and used as organocatalysts in the asymmetric epoxidation of unfunctionalized alkenes, giving rise to ees of up to 84%.

AB - A series of binaphthalene-fused azepinium salts has been generated and used as organocatalysts in the asymmetric epoxidation of unfunctionalized alkenes, giving rise to ees of up to 84%.

KW - CIS-OLEFINS

KW - ENANTIOSELECTIVE OLEFIN EPOXIDATION

KW - OXAZIRIDINIUM SALT

KW - IN-SITU

KW - OXONE

KW - DIOXIRANE

KW - TERMINAL OLEFINS

KW - OXYGEN-TRANSFER

KW - CINNAMIC ACID-DERIVATIVES

KW - AMINE-CATALYZED EPOXIDATION

U2 - 10.1021/jo070255w

DO - 10.1021/jo070255w

M3 - Article

SN - 0022-3263

VL - 72

SP - 4424

EP - 4430

JO - The Journal of Organic Chemistry

JF - The Journal of Organic Chemistry

IS - 12

ER -