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Ligand Effects on the Diastereoselectivities of Samarium Diiodide Promoted Pinacol Coupling

✍ Scribed by Henriette Lodberg Pedersen; Torben Birk Christensen; Rasmus Juel Enemærke; Kim Daasbjerg; Troels Skrydstrup

Publisher
John Wiley and Sons
Year
1999
Tongue
English
Weight
327 KB
Volume
1999
Category
Article
ISSN
1434-193X

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✦ Synopsis

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

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The Effect of Lewis Acids on the Pinacol
The Effect of Lewis Acids on the Pinacol Homocoupling Reaction of Aldehydes Promoted by Samarium Diiodide
✍ Rita Annunziata; Maurizio Benaglia; Mauro Cinquini; Laura Raimondi 📂 Article 📅 1999 🏛 John Wiley and Sons 🌐 English ⚖ 395 KB 👁 1 views

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 compl