The chiral endocyclic enecarbamate 14 has been obtained by deprotonation-elimination from the N-Boc pyrrolidine 5 (or its racemic counterpart from 15). Efficiently stereocontrolled epoxidation-methanolysis of 14 afforded ?-alkoxy carbamates, which undergo completely stereoselective nucleophilic substitutions to give trisubstituted dihydroxypyrrolidines
Studies on the Lithiation of Hydroxypyrrolidines: Synthesis of Polyhydroxylated Pyrrolidines via Chiral Enecarbamates
Reginato Gianna;
2011
Abstract
The chiral endocyclic enecarbamate 14 has been obtained by deprotonation-elimination from the N-Boc pyrrolidine 5 (or its racemic counterpart from 15). Efficiently stereocontrolled epoxidation-methanolysis of 14 afforded ?-alkoxy carbamates, which undergo completely stereoselective nucleophilic substitutions to give trisubstituted dihydroxypyrrolidinesFile in questo prodotto:
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