Preparation of Organoaluminum Reagents from Propargylic Bromides and Aluminum Activated by PbCl2 and Their Regio- and Diastereoselective Addition to Carbonyl Derivatives

✍ Scribed by Li-Na Guo; Hongjun Gao; Peter Mayer; Paul Knochel

• Publisher: John Wiley and Sons
• Year: 2010
• Tongue: English
• Weight: 337 KB
• Volume: 16
• Category: Article
• ISSN: 0947-6539
• DOI: 10.1002/chem.201000523

✦ Synopsis

Abstract

Various propargylic and allenic aluminum reagents have been easily prepared by a direct insertion of aluminum into propargylic bromides in the presence of PbCl~2~ (1 mol %). These organoaluminum reagents react with carbonyl compounds to afford the corresponding allenic alcohols or homopropargylic alcohols in good to excellent yields with high regio‐ and diastereoselectivity.