(E)-alpha-sulfonamidocrotylboronates as reagents for the stereoselective homoaldol synthesis

Authors
Schlapbach, A Hoffmann, RW
Citation
A. Schlapbach et Rw. Hoffmann, (E)-alpha-sulfonamidocrotylboronates as reagents for the stereoselective homoaldol synthesis, EUR J ORG C, (2), 2001, pp. 323-328
Citations number
47
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
ISSN journal
1434193X → ACNP
Issue
2
Year of publication
2001
Pages
323 - 328
Database
ISI
SICI code
1434-193X(200101):2<323:(ARFTS>2.0.ZU;2-6
Abstract
The alpha -sulionamidocrotylboronates 9 and 10 have been generated by nucle ophilic substitution at the alpha -chlorocrotylboronates Ib, in yields of u p to 70%. The alpha -sulfonamidocrotylboronates 9 and 10 react with aldehyd es at room temp. and 4 kbar pressure to give the anti-homoallylic alcohols 13 and 14 with high simple diastereoselectivity. These latter may be direct ly converted into the lactol ethers 15 in a one-pot procedure.