Stereoselective transformation of amines to alcohols enriched with the enantiomer formed by respectively inversion and retention of configuration

✍ Scribed by Nina Ileby; Marek Kuzma; Lindis R. Heggvik; Karsten Sørbye; Anne Fiksdahl

• Publisher: Elsevier Science
• Year: 1997
• Tongue: English
• Weight: 420 KB
• Volume: 8
• Category: Article
• ISSN: 0957-4166
• DOI: 10.1016/s0957-4166(97)00240-1

✦ Synopsis

We hereby report the transformation of the chiral amines 1-3 to the corresponding alcohols 4-6 with 90-100% inversion of stereochemistry. KNO2 and catalytic amounts of 18-crown-6 were used in the nucleophilic attack on the N,N-ditosylimide intermediates la-3a. A diazotization reaction for the corresponding preparation of the alcohols 4--6 from the respective amines 1-3 with 65-90% retention of configuration is also discussed. (~) 1997 Elsevier Science Ltd