Journal
TETRAHEDRON
Volume 65, Issue 7, Pages 1366-1372Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2008.12.045
Keywords
Direct asymmetric aldol reaction; Water; Chiral ionic liquid; Recoverable organocalatyst; alpha-Amino acid
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Funding
- Russian Foundation of Basic Research [06-03-32603, 09-03-00384]
- Russian Academy of Sciences
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New chiral ionic liquids bearing proline, serine or threonine moieties were synthesized. Compounds that contain 1-dodecylimidazolium or 4-(5-n-nonyl)-pyridinium cations and NTf2 or PF6 anions efficiently catalyze the asymmetric aldol reaction between aldehydes and ketones in the presence of water to generate aldols with high distereo- (up to 98:2) and enantioselectivity (up to >99% ee). 4-Hydroxyproline modified by the 4-(5-n-nonyl)-pyridinium hexafluorophosphate moiety retains its activity and selectivity over at least eight reaction cycles. (C) 2009 Elsevier Ltd. All rights reserved.
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