Controlled Synthesis of Regio-, Enantio-, and Diastereomers of Amino-4-pentenediols from 1,4-Pentadien-3-ol via Epoxy-4-pentenols II.erythro- andthreo-3-Amino-4-pentene-1,2-diols anderythro-2-Benzylamino-4-pentene-1,3-diol
- 1 January 1991
- journal article
- research article
- Published by Georg Thieme Verlag KG in Synthesis
- Vol. 1991 (09) , 776-782
- https://doi.org/10.1055/s-1991-26572
Abstract
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.Keywords
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