期刊
TETRAHEDRON
卷 69, 期 4, 页码 1307-1315出版社
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2012.11.097
关键词
Solvent-free; Organocatalysis; Aldol reaction; Enantioselective; Wieland-Miescher ketone
资金
- Ministerio de Ciencia e Innovacion (MICINN) [CTQ2007-62771/BQU, CTQ2010-20387, CTQ2008-05409-C02-01, CTQ2011-22649]
- Consolider Ingenio [CSD2007-00006]
- FEDER
- Generalitat Valenciana [PROMETEO/2009/039]
- DURSI-Generalitat de Catalunya [2009SGR-1441]
- University of Alicante
- EU (ORCA action) [CM0905]
- Spanish MICINN [FPU AP2009-3601]
Silica-gel supported binam-derived prolinamides are efficient organocatalysts for the direct intra-molecular and intermolecular aldol reaction under solvent-free conditions using conventional magnetic stirring. These organocatalysts in combination with benzoic acid showed similar results to those obtained under similar homogeneous reaction conditions using an organocatalyst of related structure. For the intermolecular process, the aldol products were obtained at room temperature and using only 2 equiv of the ketone with high yields, regio-, diastereo- and enantioselectivities. Under these reaction conditions, also the cross aldol reaction between aldehydes is possible. The recovered catalyst can be reused up to nine times providing similar results. More interestingly, these heterogeneous organocatalysts can be used in the intramolecular aldol reaction allowing the synthesis of the Wieland-Miescher and ketone analogues with up to 92% ee, with its reused being possible up to five times without detrimental on the obtained results. (c) 2012 Elsevier Ltd. All rights reserved.
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