Simple metal alkoxides as effective catalysts for the hetero-aldol-Tishchenko reaction

Authors
Mascarenhas, CM Duffey, MO Liu, SY Morken, JP
Citation
Cm. Mascarenhas et al., Simple metal alkoxides as effective catalysts for the hetero-aldol-Tishchenko reaction, ORG LETT, 1(9), 1999, pp. 1427-1429
Citations number
17
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
ORGANIC LETTERS
ISSN journal
15237060 → ACNP
Volume
1
Issue
9
Year of publication
1999
Pages
1427 - 1429
Database
ISI
SICI code
1523-7060(19991104)1:9<1427:SMAAEC>2.0.ZU;2-E
Abstract
[GRAPHICS] This paper reports the utility of simple metal alkoxides for the catalytic, stereoselective hetero-aldol-Tishchenko reaction (eq 1), Choice of metal a lkoxide is crucial to achieving high efficiency and stereoselectivity, Wher eas NaO-t-Bu is an effective catalyst, delivering one product in 68% yield and 99:1 stereoselection, Sm(O-i-Pr)(3) is less effective and delivers the same product in 42% yield with 4:1 stereoselection.