Journal
TETRAHEDRON-ASYMMETRY
Volume 19, Issue 24, Pages 2913-2923Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tetasy.2008.12.021
Keywords
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Funding
- Spanish Ministerio de Educacion y Ciencia (MEC) [CSD2007-00006, CTQ2007-62771/BQU, CTQ2004-00808/BQU]
- Generalitat Valenciana [CTIOIB/2002/320, GRUPOS03/134, GV05/144]
- University of Alicante
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The enantioselective 1,3-dipolar cycloaddition reaction of stabilized azomethine ylides, generated from iminoesters, with maleimides was efficiently achieved by intermediacy of an equimolar mixture of chiral (R)- or (S)-Binap and AgClO4. The high stability of the titled catalytic metal-complex to light exposure and its insolubility in toluene made possible its recovery and reutilization in other new process. In order to get a better understanding of the behavior of these chiral catalysts, we have carried out DFT1 calculations demonstrating the experimentally observed high enantio- and endo-selectivity through a very asynchronous transition state. (C) 2009 Elsevier Ltd. All rights reserved.
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