Regioselective and stereoselective c-alkylation of enamines of 2-methyl-1,3-cyclopentanedione in the presence of strong bases
Journal Article
·
· J. Org. Chem. USSR (Engl. Transl.); (United States)
OSTI ID:6008987
The conditions for the selective /alpha//prime/- and /gamma/-alkylation of the pyrrolidine enamino derivatives of 2-methyl-1,3-cyclopentanedione with allyl bromide and monobromoacetic ester in the presence of strong bases were studied. It was shown that the use of lithium diisopropylamide for the generation of a carbanion leads to the formation of the /alpha//prime/-substituted derivatives, whereas the use of lithiumbistrimethylsilylamide as a base makes it possible to obtain the /gamma/-substituted enamines of 2-methyl-1,3-cyclopentanedione. By the successive use of the two bases it is possible to synthesize the vicinally /alpha//prime/-/gamma/-substituted enamino ketones of the cyclopentane series.
- Research Organization:
- Institute of Bioorganic Chemistry, Minsk (USSR)
- OSTI ID:
- 6008987
- Journal Information:
- J. Org. Chem. USSR (Engl. Transl.); (United States), Journal Name: J. Org. Chem. USSR (Engl. Transl.); (United States) Vol. 24:7; ISSN JOCYA
- Country of Publication:
- United States
- Language:
- English
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Related Subjects
37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY
400201* -- Chemical & Physicochemical Properties
ACETIC ACID ESTERS
ALKALI METAL COMPOUNDS
ALKANES
ALKYLATING AGENTS
ALKYLATION
AMIDES
AMINES
ANIONS
AZOLES
CARBANIONS
CARBOXYLIC ACID ESTERS
CATALYTIC EFFECTS
CHARGED PARTICLES
CHEMICAL REACTIONS
CHROMATOGRAPHY
COUPLING
COUPLING CONSTANTS
CYCLOALKANES
ESTERS
HETEROCYCLIC COMPOUNDS
HYDROCARBONS
INFRARED SPECTRA
INTERMEDIATE COUPLING
IONS
J-J COUPLING
KETONES
LITHIUM COMPOUNDS
MASS SPECTRA
NMR SPECTRA
ORGANIC BROMINE COMPOUNDS
ORGANIC COMPOUNDS
ORGANIC HALOGEN COMPOUNDS
ORGANIC NITROGEN COMPOUNDS
ORGANIC SILICON COMPOUNDS
PYRROLES
PYRROLIDINES
SEPARATION PROCESSES
SPECTRA
STRUCTURAL CHEMICAL ANALYSIS
SYNTHESIS
400201* -- Chemical & Physicochemical Properties
ACETIC ACID ESTERS
ALKALI METAL COMPOUNDS
ALKANES
ALKYLATING AGENTS
ALKYLATION
AMIDES
AMINES
ANIONS
AZOLES
CARBANIONS
CARBOXYLIC ACID ESTERS
CATALYTIC EFFECTS
CHARGED PARTICLES
CHEMICAL REACTIONS
CHROMATOGRAPHY
COUPLING
COUPLING CONSTANTS
CYCLOALKANES
ESTERS
HETEROCYCLIC COMPOUNDS
HYDROCARBONS
INFRARED SPECTRA
INTERMEDIATE COUPLING
IONS
J-J COUPLING
KETONES
LITHIUM COMPOUNDS
MASS SPECTRA
NMR SPECTRA
ORGANIC BROMINE COMPOUNDS
ORGANIC COMPOUNDS
ORGANIC HALOGEN COMPOUNDS
ORGANIC NITROGEN COMPOUNDS
ORGANIC SILICON COMPOUNDS
PYRROLES
PYRROLIDINES
SEPARATION PROCESSES
SPECTRA
STRUCTURAL CHEMICAL ANALYSIS
SYNTHESIS