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A Cascade Aza‐Cope/Aza‐Prins Cyclization Leading to Piperidine Derivatives
Author(s) -
Nallasivam Jothi L.,
Fernandes Rodney A.
Publication year - 2015
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201403607
Subject(s) - chemistry , piperidine , bicyclic molecule , stereochemistry , carboxylate , cascade , tris , ligand (biochemistry) , combinatorial chemistry , medicinal chemistry , receptor , biochemistry , chromatography
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.