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Synfacts 2008(10): 1026-1026  
DOI: 10.1055/s-2008-1078164
Synthesis of Heterocycles
© Georg Thieme Verlag Stuttgart ˙ New York

Synthesis of Piperidinones via a Multicomponent Condensation

Contributor(s): Victor Snieckus, Jignesh J. Patel
P. W. Clarke*, A. V. Zaytsev, T. W. Morgan, A. C. Whitewood, C. Wilson
University of York and University of Nottingham, UK
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Publication History

Publication Date:
22 September 2008 (online)

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Significance

A four-component procedure for the synthesis of polyfunctionalized piperidin-4-ones has been developed. In this reaction, the im­ine is premixed with TiCl4 followed by the addition of diketene and methanol and finally the aldehyde component is added. Reasonable scope in terms of derived substitution patterns was studied. The resulting diastereomeric mixtures of piperidin-4-ones, obtained in good to excellent yields, were successfully converted into single diastereomers under basic conditions (K2CO3/DMF). The ste­reochemistry was assigned by single crystal X-ray structure analysis of a selected piperidinone.