Reactions of N-Phosphorylated Aziridines with Dianions Derived from Ethyl Acetoacetate and 1,3-Diketones: New Route to Substituted Pyrrolines and Pyrrolidines
- 1 April 1998
- journal article
- research article
- Published by Taylor & Francis in Synthetic Communications
- Vol. 28 (7) , 1127-1137
- https://doi.org/10.1080/00397919808005953
Abstract
The nucleophilic ring-opening of N-(diethoxyphosphory)aziridines by the dianions derived from ethyl acetoacetate and 1,3-diketones has been studied. Acid-mediated cyclisation and dephosphorylation of the resulting products to a number of substituted pyrrolines and pyrrolidines has been also investigated.Keywords
This publication has 8 references indexed in Scilit:
- Synthesis of Primary sec-alkylamines via nucleophilic ring-opening of N-phosphorylated aziridinesTetrahedron, 1997
- Two-Carbon Homologation of Grignard Reagents to Primary AminesSynthesis, 1996
- Reaction of Aziridines with Dianions Derived from β-Ketoesters: Application to the Preparation of Substituted PyrrolidinesSynlett, 1993
- Boric acid: a new regiospecific decarboxylating agent. Syntheses of cyclic imines, β-enaminones, and β-enaminodiketones from β-enaminoestersCanadian Journal of Chemistry, 1991
- Asymmetric total syntheses of elaeokanines A and B via .alpha.-sulfinyl ketimineThe Journal of Organic Chemistry, 1990
- The Decomposition of Olefinic Azides1Journal of the American Chemical Society, 1965
- Synthesis of Nicotine Analogs1The Journal of Organic Chemistry, 1958
- The Structure of Alkyl-Substituted Pyrrolines1Journal of the American Chemical Society, 1951