An easy and straightforward approach to the asymmetric synthesis of isoflavanones

✍ Scribed by Jose L. Vicario; Dolores Badı́a; Luisa Carrillo

• Publisher: Elsevier Science
• Year: 2003
• Tongue: English
• Weight: 203 KB
• Volume: 14
• Category: Article
• ISSN: 0957-4166
• DOI: 10.1016/s0957-4166(02)00831-5

✦ Synopsis

Isoflavanones 4a-d have been prepared in a stereocontrolled fashion using (S,S)-(+)-pseudoephedrine as a chiral auxiliary. The employed synthetic pathway consists of only four steps and involves initial formation of the stereogenic centre via diastereoselective aldol reaction of pseudoephedrine arylacetamides 1a-c with formaldehyde, followed by aryl ether formation under Mitsunobu conditions, removal of the chiral auxiliary by hydrolysis and final Friedel-Crafts intramolecular acylation.