Highly regioselective and diastereoselective epoxidation of allylic amines with Oxone

VK Aggarwal; GY Fang

doi:10.1039/b503516c

Highly regioselective and diastereoselective epoxidation of allylic amines with Oxone

VK Aggarwal^*, GY Fang

^*Corresponding author for this work

Research output: Contribution to journal › Article (Academic Journal) › peer-review

28 Citations (Scopus)

Abstract

Allylic amines ( as their protonated ammonium salts) can be epoxidised with high syn diastereoselectivity and regioselectivity at the proximal alkene in substrates with several double bonds using Oxone. The protonated ammonium cation activates the Oxone by hydrogen bonding, thus promoting the oxidation of groups within the vicinity of the complex.

Original language	English
Pages (from-to)	3448-3450
Number of pages	3
Journal	Chemical Communications
Issue number	27
DOIs	https://doi.org/10.1039/b503516c
Publication status	Published - 2005

Keywords

M-CHLOROPERBENZOIC ACID
CATALYZED EPOXIDATION
ALKENYLAMMONIUM SALTS
ALKENES
DIMETHYLDIOXIRANE
MECHANISM
OLEFINS

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title = "Highly regioselective and diastereoselective epoxidation of allylic amines with Oxone",

abstract = "Allylic amines ( as their protonated ammonium salts) can be epoxidised with high syn diastereoselectivity and regioselectivity at the proximal alkene in substrates with several double bonds using Oxone. The protonated ammonium cation activates the Oxone by hydrogen bonding, thus promoting the oxidation of groups within the vicinity of the complex.",

keywords = "M-CHLOROPERBENZOIC ACID, CATALYZED EPOXIDATION, ALKENYLAMMONIUM SALTS, ALKENES, DIMETHYLDIOXIRANE, MECHANISM, OLEFINS",

author = "VK Aggarwal and GY Fang",

year = "2005",

doi = "10.1039/b503516c",

language = "English",

pages = "3448--3450",

journal = "Chemical Communications",

issn = "1359-7345",

publisher = "Royal Society of Chemistry",

number = "27",

}

TY - JOUR

T1 - Highly regioselective and diastereoselective epoxidation of allylic amines with Oxone

AU - Aggarwal, VK

AU - Fang, GY

PY - 2005

Y1 - 2005

N2 - Allylic amines ( as their protonated ammonium salts) can be epoxidised with high syn diastereoselectivity and regioselectivity at the proximal alkene in substrates with several double bonds using Oxone. The protonated ammonium cation activates the Oxone by hydrogen bonding, thus promoting the oxidation of groups within the vicinity of the complex.

AB - Allylic amines ( as their protonated ammonium salts) can be epoxidised with high syn diastereoselectivity and regioselectivity at the proximal alkene in substrates with several double bonds using Oxone. The protonated ammonium cation activates the Oxone by hydrogen bonding, thus promoting the oxidation of groups within the vicinity of the complex.

KW - M-CHLOROPERBENZOIC ACID

KW - CATALYZED EPOXIDATION

KW - ALKENYLAMMONIUM SALTS

KW - ALKENES

KW - DIMETHYLDIOXIRANE

KW - MECHANISM

KW - OLEFINS

U2 - 10.1039/b503516c

DO - 10.1039/b503516c

M3 - Article (Academic Journal)

SP - 3448

EP - 3450

JO - Chemical Communications

JF - Chemical Communications

SN - 1359-7345

IS - 27

ER -

Highly regioselective and diastereoselective epoxidation of allylic amines with Oxone

Abstract

Keywords

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