Download PDF
Synthesis 1991; 1991(9): 776-782
DOI: 10.1055/s-1991-26572
paper
© 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.

Controlled Synthesis of Regio-, Enantio-, and Diastereomers of Amino-4-pentenediols from 1,4-Pentadien-3-ol via Epoxy-4-pentenols II. erythro- and threo-3-Amino-4-pentene-1,2-diols and erythro-2-Benzylamino-4-pentene-1,3-diol

Volker Jäger* , Ulrich Stahl, Walter Hümmer
  • *Institut für Organische Chemie der Universität Am Hubland, D-8700 Würzburg, Germany
Further Information

Publication History

Publication Date:
29 April 2002 (online)

  PDF Download  Permissions and Reprints All articles of this category

The regioselective reaction of amines 7 at C-3 of optically active 2,3-epoxy-4-penten-1-ol (4) and its enantiomer 5 leads to 3-amino-4-pentene-1,2-diols of both the erythro-D- and -L-series, 8, 9. The scope of this process, mediated by titanium(IV) isopropoxide in the case of hindered amines, embraces ammonia (7a) and aniline (7g) as well as diisopropylamine (7j). The threo-isomers, 10, are accessible from 4 via 3-chloro-4-pentene-1,2-diol (6) by net double inversion at C-3. Of the 2-amino-4-pentene-1,3-diol series, the N-benzyl compound of D-erythro configuration is obtained from 5 by cyclization of the intermediate carbamate 13; the like approach to the threo isomer 12 remained unsatisfactory.