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Synthesis 2007(20): 3185-3190  
DOI: 10.1055/s-2007-990792
PAPER
© Georg Thieme Verlag Stuttgart · New York

Regioselective γ-Alkylation of tert-Butyl 2,4-Dioxopiperidine-1-carboxylate

Paolo Orsini*, Alessandro Maccario, Nicoletta Colombo
Department of Chemistry, B.U. Oncology, Nerviano Medical Sciences, Viale Pasteur 10, 20014 Nerviano (MI), Italy
Fax: +39(0331)581347; e-Mail: paolo.orsini@nervianoms.com;
Further Information

Publication History

Received 19 February 2007
Publication Date:
21 September 2007 (online)

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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

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