M. Calmès, C. Didierjean, Jean Martínez
Jun 20, 2005
Citations
0
Influential Citations
13
Citations
Journal
Tetrahedron-asymmetry
Abstract
Abstract An asymmetric Diels–Alder reaction between the enantiopure ( R )-benzyl-4-(3-acryloyloxy-4,4-dimethyl-2-oxopyrrolidin-1-yl)-benzoate ( R )- 2 and the N - Z -aminodiene 3 proceeded with total endo diastereoselectivity and was facially controlled in favour of the (3′ R ,1 R ,2 S )-adduct. The two adducts obtained, 4 (the main compound) and 5 , were isolated pure after column chromatography on silica gel. Their LiOH hydrolysis followed by palladium-catalyzed hydrogenation of the double bond concomitant with hydrogenolysis of the carbamate moiety yielded the enantiopure cis -2-aminocyclohexane carboxylic acids (1 R ,2 S )- 8 and (1 S ,2 R )- 8 .