Reactions of carbon nucleophiles with 2,2,3-trisubstituted ethynylaziridines |
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Authors: | Brandon T Kelley Madeleine M Joullié |
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Institution: | Department of Chemistry, University of Pennsylvania, 231 South 34th Street, Philadelphia, PA 19104, USA |
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Abstract: | Carbon nucleophiles were used to open a 2,2,3-trisubstituted ethynylaziridine. A cyanide nucleophile opened the ring at the more substituted carbon, proceeding regioselectively with inversion of configuration. In an attempt to expand upon the scope of the reaction, Normant cuprates were reacted with a 2,2,3-trisubstituted ethynylaziridine. This reaction produced chiral allenes via an anti-SN2′ pathway. X-ray analysis of a derivative allowed the absolute stereochemistry of the anti-allenes to be assigned as P. |
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