ChemInform Abstract: Regio- and Diastereoselective Boron-Mediated Aldol Reactions of Chiral α,β,γ,δ-Unsaturated N-Acyloxazolidinones.

✍ Scribed by James M. Takacs; Mohamad R. Jaber; Benjamin J. Swanson; Steven J. Mehrman

• Publisher: John Wiley and Sons
• Year: 2010
• Weight: 35 KB
• Volume: 30
• Category: Article
• ISSN: 0931-7597
• DOI: 10.1002/chin.199926081

✦ Synopsis

1999 hydroxycarboxylic acids

hydroxycarboxylic acids (ether carboxylic acids) (acyclic compounds) and esters P 0280

26 -081

Regio-and Diastereoselective Boron-Mediated Aldol Reactions of Chiral α,β,γ,δ-Unsaturated N-Acyloxazolidinones.

-The established boron-mediated stereoselective aldol addition of crotonic acid derived N-acyloxazolidinones is extended to N-acyloxazolidinones derived from dienoic acids. With exception of compound (V) all products are obtained with high isomeric purity. Condensation of α,β-unsaturated aldehyde (IX) with N-acyloxazolidinone (VIII) requires modified reaction conditions due to the lability of the primary aldol adduct. The strategy is also successfully applied to conjugated polyene systems. -(TAKACS,