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Multipurpose box‐ and azabox‐Based Immobilized Chiral Catalysts
Author(s) -
Fraile José M.,
Pérez Ignacio,
Mayoral José A.,
Reiser Oliver
Publication year - 2006
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.200606121
Subject(s) - oxazoline , chemistry , cyclopropanation , catalysis , enantioselective synthesis , copper , aldol reaction , combinatorial chemistry , solvent , organic chemistry
Azabis(oxazolines) can be used as chiral ligands in the copper‐catalyzed enantioselective Mukaiyama aldol reaction. When supported on solids, azabis(oxazoline)‐copper complexes are more easily deactivated than their analogous bis(oxazoline)‐copper complexes, and are not compatible with the use of coordinating solvents in the method of preparation. The performance of the immobilized catalysts (up to 86 % ee ) depends on the support and the reaction solvent, with some positive effect on enantioselectivity due to surface effects. The deactivation is not irreversible and the deactivated catalysts show excellent performance in the cyclopropanation reaction, providing added value to the supported multipurpose catalysts.