Highly diastereoselective aminoalkylation of naphthols with chiral amines mediated by lithium perchlorate solution in diethyl ether

✍ Scribed by Mohammad R Saidi; Najmoddin Azizi

• Book ID: 104359630
• Publisher: Elsevier Science
• Year: 2003
• Tongue: English
• Weight: 310 KB
• Volume: 14
• Category: Article
• ISSN: 0957-4166
• DOI: 10.1016/s0957-4166(02)00863-7

✦ Synopsis

One-pot, three-component, Mannich reaction of naphthols with in situ prepared imines in 5 M ethereal lithium perchlorate at room temperature affords the corresponding aminoalkylated products in high yields with high diastereoselectivities. The process is exemplified by the reaction of 2-naphthol with (R)-1-phenylethylamine and an aromatic aldehyde in concentrated ethereal lithium perchlorate solution, which affords a highly diastereoselective access to the requisite 2-aminoalkylated product.