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The Effect of Lewis Acids on the Pinacol Homocoupling Reaction of Aldehydes Promoted by Samarium Diiodide (1999)

Annunziata, Rita ; Benaglia, Maurizio ; Cinquini, Mauro ; [et al.]

Weinheim : Wiley-Blackwell

Liebigs Annalen 1999 (1999), S. 3369-3374

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Details

ISSN: 1434-193X

Keywords: Pinacol reaction ; Lewis acid ; Samarium diiodide ; 1,2-diols ; Carbonyl compounds ; Chemistry ; General Chemistry

Source: Wiley InterScience Backfile Collection 1832-2000

Topics: Chemistry and Pharmacology

Notes: The effect of various Lewis acids on the samarium diiodide promoted pinacol homocoupling of aldehydes was investigated. The reaction of benzaldehyde proceeded with fair to good 1,2-anti-stereoselectivity, while in the case of other aromatic and aliphatic aldehydes syn-stereoselectivity was generally observed. Chiral α-alkylaldehydes allowed for an almost complete stereocontrol favoring syn-1,2-diols.

Additional Material: 5 Ill.

Type of Medium: Electronic Resource

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