A Domino Ring-Opening/Epoxidation of 1,2-Dioxines

Ben Greatrex; Dennis K Taylor; Edward R T Tiekink

doi:10.1021/jo0303315

A Domino Ring-Opening/Epoxidation of 1,2-Dioxines

Ben Greatrex
, Dennis K Taylor
, Edward R T Tiekink

Pharmacy

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

15 Citations (Scopus)

Abstract

When allowed to react with alkaline hydrogen peroxide, monocyclic 1,2-dioxines ring-open to their isomeric 'y'-hydroxyenone intermediates which are rapidly epoxidized to afford 'trans'-4-hydroxy-2,3-epoxyketones in 21-81% yield. In the case of 'meso'-1,2-dioxines, Co(II) complex catalyzed asymmetric ring-opening of the 1,2-dioxine may be employed to furnish enantioenriched epoxides.

Original language	English
Pages (from-to)	2580-2583
Journal	The Journal of Organic Chemistry
Volume	69
Issue number	7
DOIs	https://doi.org/10.1021/jo0303315
Publication status	Published - 2004

Keywords

Organic Chemical Synthesis
Organic Chemistry

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10.1021/jo0303315

https://hdl.handle.net/1959.11/15520

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title = "A Domino Ring-Opening/Epoxidation of 1,2-Dioxines",

abstract = "When allowed to react with alkaline hydrogen peroxide, monocyclic 1,2-dioxines ring-open to their isomeric 'y'-hydroxyenone intermediates which are rapidly epoxidized to afford 'trans'-4-hydroxy-2,3-epoxyketones in 21-81\% yield. In the case of 'meso'-1,2-dioxines, Co(II) complex catalyzed asymmetric ring-opening of the 1,2-dioxine may be employed to furnish enantioenriched epoxides.",

keywords = "Organic Chemical Synthesis, Organic Chemistry",

author = "Ben Greatrex and Taylor, \{Dennis K\} and Tiekink, \{Edward R T\}",

year = "2004",

doi = "10.1021/jo0303315",

language = "English",

volume = "69",

pages = "2580--2583",

journal = "The Journal of Organic Chemistry",

issn = "0022-3263",

publisher = "American Chemical Society",

number = "7",

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TY - JOUR

T1 - A Domino Ring-Opening/Epoxidation of 1,2-Dioxines

AU - Greatrex, Ben

AU - Taylor, Dennis K

AU - Tiekink, Edward R T

PY - 2004

Y1 - 2004

N2 - When allowed to react with alkaline hydrogen peroxide, monocyclic 1,2-dioxines ring-open to their isomeric 'y'-hydroxyenone intermediates which are rapidly epoxidized to afford 'trans'-4-hydroxy-2,3-epoxyketones in 21-81% yield. In the case of 'meso'-1,2-dioxines, Co(II) complex catalyzed asymmetric ring-opening of the 1,2-dioxine may be employed to furnish enantioenriched epoxides.

AB - When allowed to react with alkaline hydrogen peroxide, monocyclic 1,2-dioxines ring-open to their isomeric 'y'-hydroxyenone intermediates which are rapidly epoxidized to afford 'trans'-4-hydroxy-2,3-epoxyketones in 21-81% yield. In the case of 'meso'-1,2-dioxines, Co(II) complex catalyzed asymmetric ring-opening of the 1,2-dioxine may be employed to furnish enantioenriched epoxides.

KW - Organic Chemical Synthesis

KW - Organic Chemistry

U2 - 10.1021/jo0303315

DO - 10.1021/jo0303315

M3 - Article

SN - 0022-3263

VL - 69

SP - 2580

EP - 2583

JO - The Journal of Organic Chemistry

JF - The Journal of Organic Chemistry

IS - 7

ER -

A Domino Ring-Opening/Epoxidation of 1,2-Dioxines

Abstract

Keywords

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