Catalytic Double Stereoinduction in Asymmetric Allylic Alkylation of Oxindoles

✍ Scribed by Barry M. Trost; Yong Zhang

• Publisher: John Wiley and Sons
• Year: 2010
• Tongue: English
• Weight: 311 KB
• Volume: 16
• Category: Article
• ISSN: 0947-6539
• DOI: 10.1002/chem.200902770

✦ Synopsis

Abstract

A highly regio‐, diastereo‐, and enantioselective allylic alkylation reaction of 3‐monosubstituted oxindoles catalyzed by molybdenum is described. The reaction is affected by the electronic and steric variations of the nucleophile. The use of appropriate N‐protecting group is particularly important for achieving high regio‐ and diastereoselectivity. Products from this reaction, containing vicinal quaternary‐tertiary stereogenic centers, are valuable synthetic intermediates and should find utility in alkaloid synthesis.