Citation
R. Annunziata et al., The effect of Lewis acids on the pinacol homocoupling reaction of aldehydes promoted by samarium diiodide, EUR J ORG C, (12), 1999, pp. 3369-3374
Citations number
31
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
ISSN journal
1434193X
→ ACNP
Issue
12
Year of publication
1999
Pages
3369 - 3374
Database
ISI
SICI code
1434-193X(199912):12<3369:TEOLAO>2.0.ZU;2-V
Abstract
The effect of various Lewis acids on the samarium diiodide promoted pinacol
homocoupling of aldehydes was investigated. The reaction of benzaldehyde p
roceeded 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 stere
ocontrol favoring syn-1,2-diols.