Enantioselective direct aldol reaction "on water" promoted by chiral organic catalysts

Organic Letters

Volumn 9, Issue 7, 2007, Pages 1247-1250

  Guizzetti, Stefania ^a   Benaglia, Maurizio ^a   Raimondi, Laura ^a   Celentano, Giuseppe ^a  

^a UNIVERSITY OF MILAN   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 34147103331     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol070002p     Document Type: Article

References (32)

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22. For a very interesting discussion of enantioselective organocatalysis "in water" or "in the presence of water", see: (a) Brogan, A. P.; Dickerson, T. J.; Janda, K. D. Angew. Chem., Int. Ed. 2006, 45, 8100.
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24. 12b in defining "in the presence of water" as a more appropriate expression for reactions described in refs 6 and 7. However, it must be noted once again that the catalysts of refs 6 and 7b are the only ones working in the presence of a large excess of water, while this is not true in the other systems.
25. Guizzetti, S.; Benaglia, M.; Pignataro, L.; Puglisi, A. Tetrahedron: Asymmetry 2006, 17, 2754.
26. (a) Guillena, G.; Hita, M.; Najera, C. Tetrahedron: Asymmetry 2006, 17, 729.
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29. For other organocatalysts prepared according to these principles, see: Pignataro, L.; Benaglia, M.; Annunziata, R.; Cinquini, M.; Cozzi, F. J. Org. Chem. 2006, 71, 1458.
30. The use of acids as additive has been already reported; see refs 14 and 11b and citations within.
31. 6 Please note once again in our conditions a small excess of ketone is used and the ratio water/ketone is almost double compared to both refs 6 and 7b.
32. For a proline-based recoverable organocatalytic system for reactions in water, see ref 11c. For a general overview on recoverable chiral organic catalysts, see ref 4c and Benaglia, M. New J. Chem. 2006, 30, 1525.