Organolanthanide catalysis of Mukaiyama addition reaction

Journal Article · Thu Dec 20 23:00:00 EST 1990 · Journal of Organic Chemistry; (United States)

DOI:https://doi.org/10.1021/jo00313a002· OSTI ID:5128375

Gong, Lehi; Streitwieser, A ^[1]

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1. Lawrence Berkeley Lab., CA (United States)

Bis(bis(1,3-trimethylsilyl)cyclopentadienyl)ytterbium(III) chloride, Cp{double prime}{sub 2}YbCl, 2, is an effective catalyst in the presence of additional trimethylsiyl chloride for the reaction of silyl ester enolates, such as the trimethylsilyl enolate of methyl isobutyrate, 1, with aliphatic and aromatic aldehydes, to yield {beta}-silyoxy esters. The reaction shows good diastereoselection that is readily rationalized with a cyclic transition-state mechanism in which a key feature is the important role played by restricted coordination space around the lanthanide cation.

• DOE Contract Number: AC03-76SF00098
• OSTI ID: 5128375
• Journal Information: Journal of Organic Chemistry; (United States), Journal Name: Journal of Organic Chemistry; (United States) Vol. 55:26; ISSN 0022-3263; ISSN JOCEA
• Country of Publication: United States
• Language: English

Related Subjects

37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY
400201* -- Chemical & Physicochemical Properties
ADSORBENTS
ALCOHOLS
ALDEHYDES
ALKENES
BENZALDEHYDE
CATALYSIS
CATALYSTS
CHEMICAL PREPARATION
CHEMICAL REACTION KINETICS
CHEMICAL REACTIONS
CHROMATOGRAPHY
COMPLEXES
CYCLOALKENES
CYCLOPENTADIENE
DECOMPOSITION
DIENES
ENOLS
ESTERS
FURANS
FURFURAL
HETEROCYCLIC COMPOUNDS
HOMOGENEOUS CATALYSIS
HYDRIDES
HYDROCARBONS
HYDROGEN COMPOUNDS
HYDROLYSIS
HYDROXY COMPOUNDS
INORGANIC ACIDS
ISOMERS
KINETICS
LEWIS ACIDS
LIQUID COLUMN CHROMATOGRAPHY
LYSIS
METHYLENE CHLORIDE
MOLECULAR STRUCTURE
ORGANIC CHLORINE COMPOUNDS
ORGANIC COMPOUNDS
ORGANIC HALOGEN COMPOUNDS
ORGANIC OXYGEN COMPOUNDS
ORGANIC SILICON COMPOUNDS
ORGANOMETALLIC COMPOUNDS
POLYENES
RARE EARTH COMPLEXES
REACTION KINETICS
SEPARATION PROCESSES
SILANES
SILICA GEL
SILICON COMPOUNDS
SOLVOLYSIS
STEREOCHEMISTRY
SYNTHESIS
TETRAHYDROFURAN
YTTERBIUM COMPLEXES