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. AnnunziataPrimo
;M. BenagliaSecondo
;M. CinquiniPenultimo
;L. RaimondiUltimo
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.
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