Candida antarctica lipase-catalyzed doubly enantioselective aminolysis reactions. Chemoenzymatic synthesis of 3-hydroxypyrrolidines and 4-(silyloxy)-2-oxopyrrolidines with two stereogenic centers
Vm. Sanchez et al., Candida antarctica lipase-catalyzed doubly enantioselective aminolysis reactions. Chemoenzymatic synthesis of 3-hydroxypyrrolidines and 4-(silyloxy)-2-oxopyrrolidines with two stereogenic centers, J ORG CHEM, 64(5), 1999, pp. 1464-1470
Aminolyses of racemic and prochiral 3-hydroxyesters with racemic amines are
effectively catalyzed by Candida antarctica lipase. In these processes, th
e simultaneous resolution of the ester and the amine, or the corresponding
asymmetrization-resolution, takes place. In all cases, the high enantiosele
ctivity shown by the lipase toward all the reactants allows the preparation
of enantiopure 3-hydroxyamides with very high diastereomeric ratios. These
3-hydroxyamides are used as starting materials in the synthesis of 3-hydro
xy- and 2-oxopyrrolidines, both containing two stereogenic centers in their
structures.