Journal
ADVANCED SYNTHESIS & CATALYSIS
Volume 350, Issue 16, Pages 2467-2472Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/adsc.200800430
Keywords
aldol reaction; asymmetric catalysis; organocatalysis; prolinethioamides; solvent-free reactions
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Funding
- Generalitat Valenciana [GRMECUPOS05111, GV051144, GV120071142]
- [CTQ2004-00808/BQQ]
- [CTQ2007-62771/BQU]
- [INGENIO 2010 CSD2007-00006]
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A solvent-free asymmetric and direct anti-aldol reaction of aliphatic ketones with aromatic aldehydes catalyzed by recyclable L-proline-amides and L-prolinethioarnides 3 is studied. The L-prolinethioamide 3d (5 mol%), derived from L-Pro and (R)-1-aminoindane, is the most efficient catalyst for this process affording the anti-aldol adducts in high yields with excellent diastereo- and enantio-selectivities (up to > 98/2 dr, up to 98% ee) at 0 degrees C or room temperature. Prolinethioamide 3d is an effective organocatalyst for the first asymmetric, solvent-free, intramolecular Hajos-Parrish-Eder-Sauer-Wiechert reaction with comparable or higher levels of enantioselectivity (up to 88% ee) to reported catalysts in organic solvents. Moreover, organocatalyst 3d can be easily recovered and reused by a simple acid/base extraction.
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