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|Title:||A Cascade Aza-Cope/Aza-Prins Cyclization Leading to Piperidine Derivatives|
|Keywords:||Catalytic Asymmetric Aminoallylation|
|Publisher:||WILEY-V C H VERLAG GMBH|
|Citation:||EUROPEAN JOURNAL OF ORGANIC CHEMISTRY(9)2012-2022|
|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.|
|Appears in Collections:||Article|
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