Journal
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
Volume 2015, Issue 12, Pages 2614-2621Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.201500007
Keywords
Organocatalysis; Aldol reactions; Nitrogen heterocycles; Solvent-free process
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Funding
- Spanish Ministerio de Ciencia e Innovacion (MICINN) [CTQ2010-20387, CSD2007-00006]
- Spanish Ministerio de Economia y Competitividad (MINECO) [CTQ2013-43446-P, CTQ2014-51912-REDC]
- Fondos Europeos para el Desarrollo Regional (FEDER)
- Generalitat Valenciana [PROMETEO 2009/039, PROMETEOII/2014/017]
- Basque Government [IT-291-07]
- European Commission, FP7 Marie Curie Actions through the ITN ECHONET network [MCITN-2012-316379]
- University of Alicante
- University of the Basque Country
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Chiral L-prolinamides 2 containing the (R,R)- and (S,S)-trans-cyclohexane-1,2-diamine scaffold and a 2-pyrimidinyl unit are synthesized and used as general organocatalysts for intermolecular and intramolecular aldol reactions with 1,6-hexanedioic acid as a co-catalyst under solvent-free conditions. The intermolecular reaction between ketone-aldehyde and aldehyde-aldehyde must be performed under wet conditions with catalyst (S,S)-2b at 10 degrees C, which affords anti-aldols with high regio-, diastereo-, and enantioselectivities. For the Hajos-Parrish-Eder-Sauer-Wiechert reaction, both diastereomers of catalyst 2 give similar results at room temperature in the absence of water to give the corresponding Wieland-Miescher ketone and derivatives. Both types of reactions were scaled up to 1 g, and the organocatalysts were recovered by extractive workup and reused without any appreciable loss in activity. DFT calculations support the stereochemical results of the intermolecular process and the bifunctional role played by the organocatalyst by providing a computational comparison of the H-bonding networks occurring with catalysts 2a and 2b.
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