Download PDF
Synlett 1990; 1990(10): 587-588
DOI: 10.1055/s-1990-21174
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.

Chiral Vinyl Anions for "Carbonyl Umpolung". Non-Chelate-Controlled Addition of an Enantiomerically Pure Vinyllithium Reagent to O-Protected 3-Hydroxybutyraldehydes

Manfred Braun* , Hellmut Mahler
  • *Institut für Organische Chemie und Makromolekulare Chemie der Universität Düsseldorf, Universitätsstrasse 1, D-4000 Düsseldorf, Federal Republic of Germany
Further Information

Publication History

Publication Date:
08 March 2002 (online)

 PDF Download  Permissions and Reprints All articles of this category
Preview

(2R,4R)-2,4-Dibenzyloxy-1-pentanol (7) is available by stereoselective reaction of the chiral vinyllithium reagent 1b ((R)-1-bromo-1-lithio-3-[(2-methoxyethoxy)methoxy]-1-butene) with (R)-3-benzyloxybutyraldehyde (2). Thus, the addition of a methanol-d1-synthon (-CH2OH) to O-protected 3-hydroxybutyraldehydes is possible in a "non-chelate-controlled" manner.