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Synlett 1992; 1992(11): 895-897
DOI: 10.1055/s-1992-21532
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β-Lithiated Enamines as Enolate Equivalents in Asymmetric Michael Additions to Enoates. Highly Enantioselective Synthesis of Mono- and Disubstituted 5-Oxo Esters

Dieter Enders* , Wolfgang Karl
  • *Institut für Organische Chemie, Rheinisch-Westfälische Technische Hochschule, Professor-Pirlet-Straße 1, D-5100 Aachen, Germany
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Publication Date:
08 March 2002 (online)

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3-Mono- and anti 2,3-disubstituted tert-butyl 5-oxo-alkanoates 5 are prepared in good overall yields and high enantiomeric excesses (ee = 84 - ≥ 96%) by diastereoselective conjugate addition of chiral β-lithiated enamines to enoates, followed by quenching with water or alkyl halides and enamine hydrolysis.