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

✍ Scribed by Rita Annunziata; Maurizio Benaglia; Mauro Cinquini; Laura Raimondi

Publisher: John Wiley and Sons
Year: 1999
Tongue: English
Weight: 395 KB
Volume: 1999
Category: Article
ISSN: 1434-193X
DOI: 10.1002/(sici)1099-0690(199912)1999:12<3369::aid-ejoc3369>3.0.co;2-p

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✦ Synopsis

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

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