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The highly enantioselective 1,3-dipolar cycloaddition of alkyl glyoxylate-derived nitrones to E-crotonaldehyde catalyzed by hybrid diamines |
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| Authors: | ?ukasz WeselińskiEdyta S?yk Janusz Jurczak |
| Affiliation: | a Department of Chemistry, University of Warsaw, Pasteura 1, 02-093 Warsaw, Poland b Institute of Organic Chemistry, Polish Academy of Sciences, Kasprzaka 44/52, 01-224 Warsaw, Poland |
| Abstract: | 1,3-Dipolar cycloaddition of alkyl glyoxylate-derived nitrones to E-crotonaldehyde can be catalyzed by hybrid diamines, obtained from (S)-BINAM and l-α-amino acids. The hybrid of (S)-BINAM and l-Phe was found to be the best organocatalyst. Products were obtained in good yield and diastereoselectivity as well as high enantioselectivity (82-91% ee). Subsequent transformations into functionalized pyrrolidinones have been demonstrated. |
| Keywords: | Amino acids Asymmetric organocatalysis Binaphthyl derivatives 1,3-Dipolar cycloaddition Nitrones |
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