期刊
JOURNAL OF CATALYSIS
卷 305, 期 -, 页码 169-178出版社
ACADEMIC PRESS INC ELSEVIER SCIENCE
DOI: 10.1016/j.jcat.2013.05.010
关键词
Non-covalent support; Potassium fluoride; Asymmetric Michael addition; Enantiomeric selectivity; Strong hydrogen bond; Supersaturation degree
资金
- MINECO [CTQ2008-00947/BQU, CTQ2012-38594-C02-01]
- DEC [2009SGR623]
- ICIQ Foundation
- MINECO
- ICIQ
- European Union [291787-ICIQ-IPMP]
The development of potassium fluoride as a practical non-covalent support for a carboxylic acid containing a pyrrolidine substituent with organocatalytic activity in the asymmetric Michael addition is described. The immobilization is carried out by simply treating the catalytic ligand in dichloromethane (DCM) solution with non-anhydrous potassium fluoride (KF). XRD and FTIR results suggest that the organocatalyst is efficiently loaded onto KF through strong hydrogen bond (SHB) formation, affording the KF-supported catalyst (KF-supCAT, 8) for the direct asymmetric Michael addition of carbonyl compounds to trans-beta-nitrostyrenes. Good yields, excellent diastereoselectivities (up to 99:1 syn:anti) and excellent enantioselectivities (up to 97% ee for the syn diastereomer) are recorded in the Michael additions of cyclohexanone to trans-beta-nitrostyrenes, considerably improving previous results obtained with a closely related catalyst covalently immobilized onto polystyrene. The KF-supCAT could be recovered and recycled three times by increasing the supersaturation degree of the solution. (C) 2013 Elsevier Inc. All rights reserved.
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