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 alpha-alkylaldehydes allowed for an almost complete stereocontrol favoring syn-1,2-diols.

The effect of Lewis acids on the pinacol homocoupling reaction of aldehydes promoted by samarium diiodide / R. Annunziata, M. Benaglia, M. Cinquini, L. Raimondi. - In: EUROPEAN JOURNAL OF ORGANIC CHEMISTRY. - ISSN 1434-193X. - :12(1999), pp. 3369-3374.

The effect of Lewis acids on the pinacol homocoupling reaction of aldehydes promoted by samarium diiodide

R. Annunziata
Primo
;
M. Benaglia
Secondo
;
M. Cinquini
Penultimo
;
L. Raimondi
Ultimo
1999

Abstract

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 alpha-alkylaldehydes allowed for an almost complete stereocontrol favoring syn-1,2-diols.
1,2-Diols; Carbonyl compounds; Lewis acid; Pinacol reaction; Samarium diiodide
Settore CHIM/06 - Chimica Organica
Article (author)
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/2434/181628
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