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Digitale Medien

Ligand Effects on the Diastereoselectivities of Samarium Diiodide Promoted Pinacol Coupling (1999)

Lodberg Pedersen, Henriette ; Christensen, Torben Birk ; Enemærke, Rasmus Juel ; [weitere]

Weinheim : Wiley-Blackwell

Liebigs Annalen 1999 (1999), S. 565-572

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Details

ISSN: 1434-193X

Schlagwort(e): Pinacol coupling ; Aldehydes ; Samarium diiodide ; 1,2-Diols ; Diastereoselectivity ; Chemistry ; General Chemistry

Quelle: Wiley InterScience Backfile Collection 1832-2000

Thema: Chemie und Pharmazie

Notizen: -The samarium diiodide pinacol coupling of benzaldehyde and cyclohexanecarboxaldehyde in the presence of a variety of polyethylene glycols, including derivatives containing carbohydrates has been studied. Whereas such complexing agents allow for the formation of 1,2-diols, in the case of benzaldehyde the erythro-isomer predominates with diastereoselectivities of up to 7:1, while with cyclohexanecarboxaldehyde a stereoselectivity of up to 10:1 was observed but in favor of the threo-isomer. This divergence in the stereoselectivity of these two aldehydes suggests the presence of two different mechanisms occurring in these pinacol coupling reactions.

Zusätzliches Material: 5 Ill.

Materialart: Digitale Medien

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