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Reusable Catalysts for the Asymmetric Diels–Alder Reaction
Author(s) -
Chollet Guillaume,
Guillerez MarieGeorge,
Schulz Emmanuelle
Publication year - 2007
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.200601081
Subject(s) - cyclopentadiene , oxazoline , diels–alder reaction , catalysis , copper , chemistry , organic chemistry , reuse , combinatorial chemistry , waste management , engineering
A new method for recycling chiral bis(oxazoline)–copper complexes is described based on the formation of charge‐transfer complexes, their subsequent precipitation, and reuse after addition of new substrates. The conditions to perform this procedure were optimized in the presence of three bis(oxazoline)‐based ligands. When associated with copper salts, these ligands efficiently catalyzed the Diels–Alder reaction between cyclopentadiene and α,β‐unsaturated acyloxazolidinones. These catalysts were successfully recycled up to ten times while maintaining their high activities and enantioselectivities.