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A Cascade Aza-Cope/Aza-Prins Cyclization Leading to Piperidine Derivatives

Authors
  • NALLASIVAM, JL
  • FERNANDES, RA
Publication Date
Jan 01, 2015
Source
DSpace at IIT Bombay
Keywords
Language
English
License
Unknown
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Abstract

The cascade aza-Cope/aza-Prins cyclization of homoallylamines to give substituted piperidines has been explored. The use of glyoxalic acid as the carbonyl component afforded bicyclic structures as a result of the internal carboxylate anion trapping the intermediate cation. The unimolecular bis-, tris-, and tetrakis(homoallylamine)s efficiently delivered the appended bis-, tris- and tetrakis(piperidine-4-ol)s (tripod and crucifix shape, respectively) as new entities. The latter compound served as an excellent ligand in the Suzuki-Miyaura cross-coupling reaction to synthesize incrustoporin.

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