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Synthesis of enantiopure trans-N-Boc-3-aminobicyclo[2.2.2]octane-2-carboxylic acids and their bicyclic 1,3-amino alcohol derivatives via the [4+2] cycloaddition of 1,3-cyclohexadiene to a chiral b-nitroacrylate
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Synthesis of enantiopure trans-N-Boc-3-aminobicyclo[2.2.2]octane-2-carboxylic acids and their bicyclic 1,3-amino alcohol derivatives via the [4+2] cycloaddition of 1,3-cyclohexadiene to a chiral b-nitroacrylate

Monique Calmes, Françoise Escale, Claude Didierjean et Jean Martinez
Chirality, Vol.23, pp.245-249
2011
DOI: https://doi.org/10.1002/chir.20906

Résumé

Asymmetric synthesis Diels-Alder reactions bicyclic b-amino acids bicyclic-1 3-amino alcohol chiral b-nitroacrylate
The chiral b-nitroacrylate 2 derived from the (R)- or (S)-4-(3-hydroxy-4,4-dimethyl-2-oxopyrrolidin-1-yl) benzoic acid 1 acts as a reactive dienophile in a diastereoselective Diels-Alder reaction with 1,3-cyclohexadiene. The major cycloadducts have been isolated and transformed into enantiopure trans (2S,3S)- or (2R,3R)- N-Boc-3-aminobicyclic[2,2,2]octane-2-carboxylic acids 5. The trans- (2S,3S)- or (2R,3R)-N-Boc 3-(hydoxymethyl)-2-aminobicyclic[2,2,2]octane 6 derivatives were also obtained.

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