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Synlett 1996; 1996(1): 87-88
DOI: 10.1055/s-1996-5302
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Allenyl Enolates - A New Class of Chiral Ambident Nucleophiles, 41: Axis to Center Chirality Transfer in Aldol Reactions of Allenyl Enolates

Michael Laux, Norbert Krause* , Ulrich Koop
  • *Institut für Organische Chemie und Biochemie der Universität Bonn, Gerhard-Domagk-Straße 1, D-53121 Bonn, Germany
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Publikationsdatum:
31. Dezember 2000 (online)

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Aldol reactions of the allenyl enolate prepared from ethyl 5,6,6-trimethyl-3,4-heptadienoate (1) and LDA proceed with good diastereofacial selectivity and simple diastereoselection if the lithium enolate is transmetalated with magnesium bromide etherate. This axis to center chirality transfer was utilized in the synthesis of enantiomerically pure ethyl (2R,3S)-4,4-dimethyl-3-hydroxy-2-hydroxymethylpentanoate (7).

Allenes - Allenyl Enolates - Chirality Transfer - Aldol Reaction - Stereoselective Synthesis