Synthesis, Table of Contents PAPER © Georg Thieme Verlag Stuttgart · New York Regioselective γ-Alkylation of tert-Butyl 2,4-Dioxopiperidine-1-carboxylate Paolo Orsini*, Alessandro Maccario, Nicoletta ColomboDepartment of Chemistry, B.U. Oncology, Nerviano Medical Sciences, Viale Pasteur 10, 20014 Nerviano (MI), ItalyFax: +39(0331)581347; e-Mail: paolo.orsini@nervianoms.com; Recommend Article Abstract Buy Article All articles of this category Abstract A method for the regioselective γ-alkylation of N-Boc protected piperidine-2,4-dione is reported. The use of a wide variety of electrophiles demonstrates the robustness of the procedure. The reaction offers facile access to synthetically useful derivatives. A mechanistic hypothesis is given, explaining the essential role played by the lithium counter-ion. Key words γ-alkylation - regioselectivity - carbanions - β-ketoamides - piperidine-2,4-dione Full Text References References 1 Thompson CM. Green DLC. Tetrahedron 1991, 47: 4223 2 Thompson CM. Dianion Chemistry in Organic Synthesis CRC Press Inc.; Boca Raton: 1994. 3 D’Alessio R, Tibolla M, Varasi M, Vanotti E, Montagnoli A, Santocanale C, Martina K, and Menichincheri M. inventors; WO 2005/013986. 4 D’Alessio R, Tibolla M, Varasi M, Vanotti E, Montagnoli A, Santocanale C, Orsini P, and Pillan A. inventors; WO 2005/014572. 5 Weiler L. J. Am. Chem. Soc. 1970, 92: 6702 6 Huckin SN. Weiler L. J. Am. Chem. Soc. 1974, 96: 1082 7 Szczecinski P. Gryff-Keller A. Molchanov S. J. Org. Chem. 2006, 71: 4636 8 Ibenmoussa S. Chavignon O. Teulade J. Viols H. Debouzy J. Chapat J. Gueiffier A. Heterocycl. Commun. 1998, 4: 317 9 Colombo M. Riccardi-Sirtori F. Rizzo V. Rapid Commun. Mass Spectrom. 2004, 18: 511
