Journal
CATALYSIS LETTERS
Volume 129, Issue 3-4, Pages 367-375Publisher
SPRINGER
DOI: 10.1007/s10562-008-9793-x
Keywords
Enantioselective epoxidation; Chiral Mn(III) salen complex; Laponite; MCM-41; FSM-16; Covalent anchoring
Categories
Funding
- FCT Fundacao para a Ciencia e a Tecnologia (FCT)
- FEDER [POCI/CTM/56192/2004]
- Fundação para a Ciência e a Tecnologia [POCI/CTM/56192/2004] Funding Source: FCT
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The Jacobsen catalyst derivative, (R,R)-[Mn(3,5-dtButsalhd)]ClO4-CAT 2, was immobilized through axial coordination of the metal center onto a Laponite, MCM-41 and FSM-16 functionalized with 3-aminopropyltriethoxysilane. The catalytic activity of the Mn-based materials was screened for the enantioselective epoxidation of three olefins: styrene, alpha-methylstyrene and 6-CN-2,2'-dimethychromene, using m-CPBA/NMO as oxidant, and the results were compared with the corresponding homogenous complex (CAT 2) and with the Jacobsen's catalyst, (R,R)-[Mn(3,5-dtButsalhd)Cl]-CAT 1. The results indicate that under comparable condition, the Laponite-based materials show both, higher epoxide yield and enantiomeric excess (ee%) compared to MCM-41 and FSM-16-based materials. The best ee% value was obtained for the substrate 6-CN-2,2'-dimethylchromene (64%) which is very close to that obtained with CAT 2 (67%) in homogeneous phase; for the two regular mesoporous materials (MCM-41 and FSM-16) the catalytic results were more favorable for the FSM-16 samples.
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