Manganese(III) acetate-mediated alkylation of beta-keto esters and beta-keto amides: an enantio- and diastereo-selective approach to substituted pyrrolidinones

G  Bar; A F  Parsons; C B  Thomas

doi:10.1039/b209123b

Manganese(III) acetate-mediated alkylation of beta-keto esters and beta-keto amides: an enantio- and diastereo-selective approach to substituted pyrrolidinones

G Bar, A F Parsons, C B Thomas

Chemistry

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

Abstract

beta-Keto esters and beta-keto amides can be efficiently alkylated on reaction with enol ethers and manganese(III) acetate in the presence of copper(II) acetate. These intermolecular radical addition reactions can be used to construct quaternary carbon centres in excellent yield and this method has been utilised in a diastereoselective approach to substituted pyrrolidinones.

Original language	English
Pages (from-to)	373-380
Number of pages	8
Journal	Organic and Biomolecular Chemistry
Volume	1
Issue number	2
DOIs	https://doi.org/10.1039/b209123b
Publication status	Published - 21 Jan 2003

Keywords

FREE-RADICAL CYCLIZATIONS
BOND-FORMING REACTIONS
(S)-PYROGLUTAMIC ACID
ASYMMETRIC INDUCTION
ENOL ETHERS
MN(III)-PROMOTED ANNULATION
PROMOTED ADDITIONS
MN(III)
CARBONUCLEOPHILES
ACETONYLATION

Access to Document

10.1039/b209123b

Cite this

@article{7e920169b13f4051870f189bdfe7ee6b,

title = "Manganese(III) acetate-mediated alkylation of beta-keto esters and beta-keto amides: an enantio- and diastereo-selective approach to substituted pyrrolidinones",

abstract = "beta-Keto esters and beta-keto amides can be efficiently alkylated on reaction with enol ethers and manganese(III) acetate in the presence of copper(II) acetate. These intermolecular radical addition reactions can be used to construct quaternary carbon centres in excellent yield and this method has been utilised in a diastereoselective approach to substituted pyrrolidinones.",

keywords = "FREE-RADICAL CYCLIZATIONS, BOND-FORMING REACTIONS, (S)-PYROGLUTAMIC ACID, ASYMMETRIC INDUCTION, ENOL ETHERS, MN(III)-PROMOTED ANNULATION, PROMOTED ADDITIONS, MN(III), CARBONUCLEOPHILES, ACETONYLATION",

author = "G Bar and Parsons, {A F} and Thomas, {C B}",

year = "2003",

month = jan,

day = "21",

doi = "10.1039/b209123b",

language = "English",

volume = "1",

pages = "373--380",

journal = "Organic and Biomolecular Chemistry",

issn = "1477-0520",

publisher = "The Royal Society of Chemistry",

number = "2",

}

TY - JOUR

T1 - Manganese(III) acetate-mediated alkylation of beta-keto esters and beta-keto amides: an enantio- and diastereo-selective approach to substituted pyrrolidinones

AU - Bar, G

AU - Parsons, A F

AU - Thomas, C B

PY - 2003/1/21

Y1 - 2003/1/21

N2 - beta-Keto esters and beta-keto amides can be efficiently alkylated on reaction with enol ethers and manganese(III) acetate in the presence of copper(II) acetate. These intermolecular radical addition reactions can be used to construct quaternary carbon centres in excellent yield and this method has been utilised in a diastereoselective approach to substituted pyrrolidinones.

AB - beta-Keto esters and beta-keto amides can be efficiently alkylated on reaction with enol ethers and manganese(III) acetate in the presence of copper(II) acetate. These intermolecular radical addition reactions can be used to construct quaternary carbon centres in excellent yield and this method has been utilised in a diastereoselective approach to substituted pyrrolidinones.

KW - FREE-RADICAL CYCLIZATIONS

KW - BOND-FORMING REACTIONS

KW - (S)-PYROGLUTAMIC ACID

KW - ASYMMETRIC INDUCTION

KW - ENOL ETHERS

KW - MN(III)-PROMOTED ANNULATION

KW - PROMOTED ADDITIONS

KW - MN(III)

KW - CARBONUCLEOPHILES

KW - ACETONYLATION

U2 - 10.1039/b209123b

DO - 10.1039/b209123b

M3 - Article

VL - 1

SP - 373

EP - 380

JO - Organic and Biomolecular Chemistry

JF - Organic and Biomolecular Chemistry

SN - 1477-0520

IS - 2

ER -