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Synfacts 2013; 9(1): 0114
DOI: 10.1055/s-0032-1317913
DOI: 10.1055/s-0032-1317913
Polymer-Supported Synthesis
Asymmetric Aldol Reaction with BINAM-Sulfonyl Polymeric Organocatalyst
Bañón-Caballero A, Guillena G, * Nájera C. * Universidad de Alicante, Spain
Cross-Linked-Polymer-Supported N-{2′-[(Arylsulfonyl)amino][1,1′-binaphthalen]-2-yl}prolinamide as Organocatalyst for the Direct Aldol Intermolecular Reaction under Solvent-Free Conditions.
Helv. Chim. Acta 2012;
95: 1831-1841
Cross-Linked-Polymer-Supported N-{2′-[(Arylsulfonyl)amino][1,1′-binaphthalen]-2-yl}prolinamide as Organocatalyst for the Direct Aldol Intermolecular Reaction under Solvent-Free Conditions.
Helv. Chim. Acta 2012;
95: 1831-1841
Further Information
Publication History
Publication Date:
17 December 2012 (online)
Significance
The BINAM-sulfonyl polymeric organocatalyst 2 was prepared by the AIBN-promoted copolymerization of BINAM-derived sulfonamide 1, styrene, and divinylbenzene (eq. 1). Polymer 2 catalyzed the asymmetric aldol reaction of aliphatic ketones with aromatic aldehydes to give the corresponding aldol products 3 in up to 89% yield with up to 95% ee (9 examples, eq. 2).
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Comment
In the aldol reaction of cyclohexanone with 4-nitrobenzaldehyde, the catalyst was recovered by filtration and reused six times with a slight decrease in its catalytic activity (1st reuse: 90% yield, 90% ee, anti/syn = 87:13, 6th reuse: 77% yield, 92% ee, anti/syn = 86:16).
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