Swern oxidation of tryptamine derivatives

✍ Scribed by Patrick D. Bailey; Philip J. Cochrane; Frances Irvine; Keith M. Morgan; David P.J. Pearson; Kenneth T. Veal

• Book ID: 104261475
• Publisher: Elsevier Science
• Year: 1999
• Tongue: French
• Weight: 255 KB
• Volume: 40
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(99)00692-9

✦ Synopsis

The Swem oxidation of various indolic substrates is described, and a range of products resulting from overall oxidation at the 2-position were observed. In particular, depending on the substrate and reaction conditions, it was possible to achieve direct oxidation to cc,/5-unsaturated systems at the 2-position, to introduce a nueleophile at the 2-position, and to introduce a CH3-S-CH2 group at the indole 4-position via an unprecedented rearrangement of a Swern intermediate.