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

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.