Highly Diastereoselective [3+2] Cycloadditions Between Non-Racemic p-Tolylsulfinimines and Iminoesters: An Efficient Entry to Enantiopure Imidazolidines and Vicinal Diaminoalcohols |
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Authors: | Alma Viso Roberto Fernández de la Pradilla Ana García Carlos Guerrero-Strachan Marta Alonso Mariola Tortosa |
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Affiliation: | Instituto de Química Orgánica, CSIC , Madrid, Spain |
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Abstract: | Abstract Readily available p-tolylsulfinimines undergo highly stereoselective [3 + 2] cycloadditions with azomethine ylides generated from α -iminoesters and LDA to produce N-sulfinylimidazolidines. In the presence of Lewis acids, p-tolylsulfinimines react with glycine iminoester enolates to produce N-sulfinylimidazolidines, after cyclization of open chain intermediates. These mechanistically diverse processes take place with excellent regio-, stereo-, and facial selectivities, and the latter is opposite to most known reactions involving sulfinimines. Some of the resulting imidazolidines have been transformed into examples of a novel class of nonsymmetrical vicinal diamines using reductive and/or hydrolytic protocols. |
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Keywords: | 1,2-Diamines asymmetric cycloadditions imidazolidines sulfinimines |
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