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Synthesis 1991; 1991(9): 776-782
DOI: 10.1055/s-1991-26572
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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
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Publication Date:
29 April 2002 (online)

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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.

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