ChemInform Abstract: Organoaluminum-Promoted Rearrangement of Epoxysilanes to α- Silylaldehydes.

✍ Scribed by T. OOI; T. KIBA; K. MARUOKA

• Publisher: John Wiley and Sons
• Year: 2010
• Weight: 34 KB
• Volume: 28
• Category: Article
• ISSN: 0931-7597
• DOI: 10.1002/chin.199743175

✦ Synopsis

Organoaluminum-Promoted Rearrangement of Epoxysilanes to α-Silylaldehydes.

-Selective rearrangement of epoxysilanes to αsilylaldehydes is achieved with high efficiency by using the exceptionally bulky Lewis acid MABR as s stoichiometric reagent. Rearrangement of deuterated derivatives (III) and (V) confirm that the migratory aptitude is governed by the stability of the cation at the more substituted carbon center. Catalytic use of MBAR leads to silyl enol ether (X) in good yield. -(OOI, T.; KIBA, T.;