β-Lithiated Enamines as Enolate Equivalents in Asymmetric Michael Additions to Enoates. Highly Enantioselective Synthesis of Mono- and Disubstituted 5-Oxo Esters
- 1 January 1992
- journal article
- letter
- Published by Georg Thieme Verlag KG in Synlett
- Vol. 1992 (11) , 895-897
- https://doi.org/10.1055/s-1992-21532
Abstract
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.Keywords
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