Journal
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
Volume 2011, Issue 14, Pages 2678-2684Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.201100041
Keywords
Asymmetric catalysis; Aza-Michael reactions; Lanthanides; Samarium; Nonlinear effect
Categories
Funding
- Centre National de la Recherche Scientifique (CNRS)
- Ministere de l'Education Nationale de l'Enseignement Superieur et de la Recherche
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Samarium diiodide is an efficient catalyst for the aza-Michael addition of O-benzylhydroxylamine to alpha,beta-unsaturated N-acyloxazolidinones leading to mixtures of the Michael adduct and the product resulting from its amidation. Samarium iodobinaphtholate catalyzed reactions selectively afford the Michael adducts with enantiomeric excesses up to 88%. An isoinversion effect with temperature is observed with the highest enantiomeric excess at -40 degrees C.
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