Unusual oxidative rearrangement of 1,5-diazadecalin

✍ Scribed by Xiaolin Li; Zhenrong Xu; Erin F DiMauro; Marisa C Kozlowski

• Book ID: 104250978
• Publisher: Elsevier Science
• Year: 2002
• Tongue: French
• Weight: 147 KB
• Volume: 43
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(02)00559-2

✦ Synopsis

Upon treatment with (PhIO) n or PhI(OAc) 2 , 1,5-diaza-cis-decalin undergoes oxidation at the more hindered position along with fragmentation to yield the ring-expanded bislactam. The cis and trans 1,5-diazadecalins both undergo the same elimination indicating a potential stereoelectronic preference for oxidation at the more substituted carbon alpha to the nitrogen. Oxidation at the less hindered positions of 1,5-diaza-cis-decalin was accomplished on the Boc-protected derivative to provide an intermediate for the synthesis of 2,6-substituted-1,5-diaza-cis-decalins.