Synthesis of enantiomerically pure constrained gamma-hydroxy-alfa-amino acids by directed hydroxylation
- Avenoza, A. 2
- Cativiela, C. 1
- París, M. 2
- Peregrina, J.M. 2
- Saenz-Torre, B. 2
-
1
Instituto de Nanociencia y Materiales de Aragón
info
-
2
Universidad de La Rioja
info
ISSN: 0957-4166
Any de publicació: 1997
Volum: 8
Número: 7
Pàgines: 1123-1129
Tipus: Article
Altres publicacions en: Tetrahedron: Asymmetry
Resum
Efficient synthetic routes to enantiomerically pure (1R,3R,6R)- and (1S,3S,6S)-1-amino-3-hydroxy-6-phenylcyclohexane-1- carboxylic acids have been developed. The key step is a directed hydroxylation through an iodo-initiated O-functionalization reaction of methyl (1S,6R)- and (1R,6S)-1-aminocarbonyl-6-phenyl-3-cyclohexene-1- carboxylates, which can easily be obtained from the asymmetric Diels-Alder reactions of 1,3-butadiene with the (E)-2-cyanocinnamates of (S)-ethyl lactate and (R)-pantolactone, respectively.