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Scandium(III)‐Zeolites as New Heterogeneous Catalysts for Imino‐Diels–Alder Reactions
Author(s) -
Olmos Andrea,
Louis Benoit,
Pale Patrick
Publication year - 2012
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201103624
Subject(s) - catalysis , zeolite , scandium , piperidine , chemistry , imine , diels–alder reaction , organic chemistry , heterogeneous catalysis , combinatorial chemistry
Abstract This study demonstrates the first zeolite‐catalyzed synthesis of piperidine derivatives, including peptidomimetics and indoloquinolizidine alkaloids. The approach developed utilizes a highly effective one‐pot reaction cascade, through imine formation and imino‐Diels–Alder reactions, promoted by scandium‐loaded zeolites as a heterogeneous catalyst. The methodology described benefits from very low catalyst loadings (≤5 mol % of Sc III ), commercially and readily available starting materials, and mild reaction conditions. Furthermore, the Sc III ‐zeolite catalyst can be readily reused more than 10 times without any loss in efficiency.