Mechanistic and stereochemical aspects of the Lewis acid mediated cleavage of α-aminoacetals

✍ Scribed by Mark A Graham; Alan H Wadsworth; Mark Thornton-Pett; Benedetta Carrozzini; Giovanni L Cascarano; Christopher M Rayner

• Book ID: 104230364
• Publisher: Elsevier Science
• Year: 2001
• Tongue: French
• Weight: 121 KB
• Volume: 42
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(01)00292-1

✦ Synopsis

The TMSOTf mediated nucleophilic cleavage of a-aminoacetals can be used to prepare a variety of substituted amines, with variable levels of stereocontrol depending on the substitution patterns. The reaction most likely proceeds via either an a-alkoxy aziridinium ion or an a-oxocarbenium ion depending on the type of nucleophile.