Synlett 1996; 1996(1): 87-88
DOI: 10.1055/s-1996-5302
letter
© Georg Thieme Verlag, Rüdigerstr. 14, 70469 Stuttgart, Germany. All rights reserved. This journal, including all individual contributions and illustrations published therein, is legally protected by copyright for the duration of the copyright period. Any use, exploitation or commercialization outside the narrow limits set by copyright legislation, without the publisher's consent, is illegal and liable to criminal prosecution. This applies in particular to photostat reproduction, copying, cyclostyling, mimeographing or duplication of any kind, translating, preparation of microfilms, and electronic data processing and storage.

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
Further Information

Publication History

Publication Date:
31 December 2000 (online)

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).

    >