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Asymmetric Carbon‐Carbon Bond Forming Reactions Catalysed by Metal(II) Bis(oxazoline) Complexes Immobilized using Supported Ionic Liquids
Author(s) -
Goodrich P.,
Hardacre C.,
Paun C.,
Ribeiro A.,
Kennedy S.,
Lourenço M. J. V.,
Manyar H.,
de Castro C. A. Nieto,
Besnea M.,
Pârvulescu V. I.
Publication year - 2011
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.201000953
Subject(s) - chemistry , oxazoline , cyclopentadiene , enantioselective synthesis , ionic liquid , aldol reaction , carbon–carbon bond , catalysis , ionic bonding , covalent bond , carbon fibers , metal , organic chemistry , diels–alder reaction , polymer chemistry , ion , materials science , composite number , composite material
Abstract A series of bis(oxazoline) metal(II) complexes has been supported on silica and carbon supports by non‐covalent immobilisation using an ionic liquid. The catalytic performance of these solids was compared for the enantioselective Diels–Alder reaction between N ‐acryloyloxazolidinone and cyclopentadiene and the Mukaiyama‐aldol reaction between methyl pyruvate and 1‐methoxy‐1‐trimethylsilyloxypropene. In both reactions the enantioselectivity was strongly influenced by the choice of support displaying enantioselectivies ( ee values) up to 40% higher than those conducted under homogeneous reaction conditions.