Intramolecular reductive coupling reactions promoted by samarium diiodide

Journal Article · Wed Oct 11 00:00:00 EDT 1989 · Journal of the American Chemical Society; (USA)

DOI:https://doi.org/10.1021/ja00203a027· OSTI ID:6947870

Molander, G A; Kenny, C ^[1]

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1. Univ. of Colorado, Boulder (USA)

Samarium diiodide is a useful reagent for promoting intramolecular reductive coupling reactions, generating functionalized carbocycles. Ketone-olefin coupling, pinacolic coupling, and other related reductive coupling reactions are accomplished under mild conditions with samarium diiodide. Products are accessed in high yield, and in many cases excellent stereochemical control is achieved at three contiguous stereocenters. Factors controlling the stereochemical outcome of these reactions are discussed, and mechanistic considerations are also outlined.

• OSTI ID: 6947870
• Journal Information: Journal of the American Chemical Society; (USA), Journal Name: Journal of the American Chemical Society; (USA) Vol. 111:21; ISSN 0002-7863; ISSN JACSA
• Country of Publication: United States
• Language: English

Related Subjects

37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY
400200* -- Inorganic
Organic
& Physical Chemistry
CHALCOGENIDES
CHEMICAL REACTIONS
COUPLING
DATA
DATA ANALYSIS
EXPERIMENTAL DATA
INFORMATION
MEASURING INSTRUMENTS
MEASURING METHODS
NUMERICAL DATA
OXIDES
OXYGEN COMPOUNDS
RARE EARTH COMPOUNDS
SAMARIUM COMPOUNDS
SAMARIUM OXIDES
STEREOCHEMISTRY