One-pot synthesis of chiral multifunctionalized aziridines |
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Authors: | Stefania Fioravanti Paolo A. Tardella |
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Affiliation: | Dipartimento di Chimica, Università degli Studi ‘La Sapienza’, P.le Aldo Moro 2, I-00185 Roma, Italy |
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Abstract: | A direct synthetic procedure to obtain chiral aziridines is reported, involving a diastereoselective aza-MIRC (Michael Initiated Ring Closure) reaction. Multifunctionalized aziridines are obtained in high overall yields (82-92%) and with a diastereomeric ratio up to 99:1. Further synthetic elaboration can lead to the formation of interesting biochemical molecules, such as amino glycosides. The diastereomeric induction seems to be strongly controlled both by the choice of chiral moiety and by the electron withdrawing groups (EWG) present on the starting alkenes. |
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Keywords: | Michael addition Amination Asymmetric induction Heterocycles |
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