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Asymmetric Diels-Alder reaction using a new chiral ß-nitroacrylate for enantiopur trans-ß-norbornane amino acid preparation
Journal article   Peer reviewed

Asymmetric Diels-Alder reaction using a new chiral ß-nitroacrylate for enantiopur trans-ß-norbornane amino acid preparation

Monique Calmes, Francoise Escale, Claude Didierjean, Guillaume Cazals and Jean Martinez
Tetrahedron: Asymmetry, Vol.18, pp.2491-2496
23/10/2007

Abstract

The main nitronorbornene adduct derived from the asymmetric Diels-Alder reaction of (S)-benzyl-4-(3-(3-nitroacryloyloxy)-4,4-dimethyl-2-oxopyrrolidin-1-yl)benzoate (S)-1 and cyclopentadiene was isolated and transformed to afford the enantiopure bicyclic ß-amino acid (1S,2R,3R,4R)-trans-ß-norbornane amino acid 9. The enantiomer (1R,2S,3S,4S)-9 could be obtained by the same synthetic route by using the chiral auxiliary (R)-1.
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