Manganese(III) acetate-mediated alkylation of 1,3-dicarbonyls to form tricarbonyl compounds bearing a quaternary carbon centre

G  Bar; A F  Parsons; C B  Thomas

Manganese(III) acetate-mediated alkylation of 1,3-dicarbonyls to form tricarbonyl compounds bearing a quaternary carbon centre

G Bar, A F Parsons, C B Thomas

Chemistry

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

Abstract

1,3-Dicarbonyl compounds including ethyl 2-methylacetoacetate can be efficiently alkylated with enol ethers or enol esters in the presence of manganese(III) acetate. These intermolecular radical addition reactions can be used to form sterically congested quaternary carbon centres in excellent yield (81-97%).

Original language	English
Pages (from-to)	1069-1072
Number of pages	4
Journal	Synlett
Issue number	7
Publication status	Published - Jul 2002

Keywords

aldehydes
alkylations. ketones
manganese
radical reactions
FREE-RADICAL CYCLIZATIONS
BETA-KETO-ESTERS
ENOL ETHERS
MN(III)-PROMOTED ANNULATION
PROMOTED ADDITIONS
OXIDATION
CARBONUCLEOPHILES
ACETONYLATION
ALKALOIDS
REAGENT

Cite this

@article{ce6d0425281a448eb70c6bb56d6d4561,

title = "Manganese(III) acetate-mediated alkylation of 1,3-dicarbonyls to form tricarbonyl compounds bearing a quaternary carbon centre",

abstract = "1,3-Dicarbonyl compounds including ethyl 2-methylacetoacetate can be efficiently alkylated with enol ethers or enol esters in the presence of manganese(III) acetate. These intermolecular radical addition reactions can be used to form sterically congested quaternary carbon centres in excellent yield (81-97%).",

keywords = "aldehydes, alkylations. ketones, manganese, radical reactions, FREE-RADICAL CYCLIZATIONS, BETA-KETO-ESTERS, ENOL ETHERS, MN(III)-PROMOTED ANNULATION, PROMOTED ADDITIONS, OXIDATION, CARBONUCLEOPHILES, ACETONYLATION, ALKALOIDS, REAGENT",

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

year = "2002",

month = jul,

language = "English",

pages = "1069--1072",

journal = "Synlett",

issn = "1437-2096",

publisher = "Georg Thieme Verlag",

number = "7",

}

TY - JOUR

T1 - Manganese(III) acetate-mediated alkylation of 1,3-dicarbonyls to form tricarbonyl compounds bearing a quaternary carbon centre

AU - Bar, G

AU - Parsons, A F

AU - Thomas, C B

PY - 2002/7

Y1 - 2002/7

N2 - 1,3-Dicarbonyl compounds including ethyl 2-methylacetoacetate can be efficiently alkylated with enol ethers or enol esters in the presence of manganese(III) acetate. These intermolecular radical addition reactions can be used to form sterically congested quaternary carbon centres in excellent yield (81-97%).

AB - 1,3-Dicarbonyl compounds including ethyl 2-methylacetoacetate can be efficiently alkylated with enol ethers or enol esters in the presence of manganese(III) acetate. These intermolecular radical addition reactions can be used to form sterically congested quaternary carbon centres in excellent yield (81-97%).

KW - aldehydes

KW - alkylations. ketones

KW - manganese

KW - radical reactions

KW - FREE-RADICAL CYCLIZATIONS

KW - BETA-KETO-ESTERS

KW - ENOL ETHERS

KW - MN(III)-PROMOTED ANNULATION

KW - PROMOTED ADDITIONS

KW - OXIDATION

KW - CARBONUCLEOPHILES

KW - ACETONYLATION

KW - ALKALOIDS

KW - REAGENT

M3 - Article

SN - 1437-2096

SP - 1069

EP - 1072

JO - Synlett

JF - Synlett

IS - 7

ER -