Journal
TETRAHEDRON
Volume 66, Issue 2, Pages 513-518Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2009.11.033
Keywords
Asymmetric catalysis; Aldol reaction; Chiral ionic liquid; Recoverable organocatalyst; Prolinamide; Water
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Funding
- Russian Foundation of Basic Research [09-03-00384, 09-03-12164]
- Russian Academy of Sciences
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New prolinamide derivatives modified with ionic liquid moieties were synthesized and studied as organocatalysts in asymmetric aldol reactions in water. Aldol reactions between cycloalkanones or methylketones and aromatic aldehydes proceeded under studied conditions with high conversions (yields), diastereo- and enantioselectivities in the presence of a hydrophobic catalyst bearing a PF6 anion (1-5 mol%). The procedure is scalable and the catalyst retained its diastereo- and enantioselectivity over at least four reaction cycles and its activity over at least three reaction cycles. (C) 2009 Elsevier Ltd. All rights reserved.
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