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Synthesis 1991; 1991(8): 649-654
DOI: 10.1055/s-1991-26536
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ß-Lithiated Enamines as Enolate Equivalents in Michael Additions to Enoates. A Novel Entry to Mono- and Disubstituted 5-Oxo Esters

Lucette Duhamel* , Pierre Duhamel, Dieter Enders, Wolfgang Karl, Frederic Leger, Jean M. Poirier, Gerhard Raabe
  • *Laboratoire de Chimie Organique, Faculté des Sciences et des Techniques de Rouen, F-76130 Mont Saint Aignan, France
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Publikationsdatum:
29. April 2002 (online)

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Mono-, di- and trisubstituted tert-butyl 5-amino-4-alkenoates 3 and mono- or disubstituted tert-butyl 5-oxoalkanoates 4 are prepared in good overall yield by conjugate addition of ß-lithiated enamines to enoates, followed by quenching with water or iodo-methane. In all cases, only one stereoisomer of the polysubstituted enamino esters 3 is produced (de > 98%).