Barry M Trost1, Yong Zhang. 1. Department of Chemistry, Stanford University, Stanford, CA 94305, USA. bmtrost@stanford.edu
Abstract
A highly regio-, diastereo-, and enantioselective allylic alkylation reaction of 3-monosubstituted oxindoles catalyzed by molybdenum is described. The reaction is affected by the electronic and steric variations of the nucleophile. The use of appropriate N-protecting group is particularly important for achieving high regio- and diastereoselectivity. Products from this reaction, containing vicinal quaternary-tertiary stereogenic centers, are valuable synthetic intermediates and should find utility in alkaloid synthesis.
A highly regio-, diastereo-, and enantioselective allylic alkylation reaction of 3-monosubstituted oxindoles catalyzed by molybdenum is described. The reaction is affected by the electronic and steric vn class="Chemical">ariations of the nucleophile. The use of appropriate N-protecting group is particularly important for achieving high regio- and diastereoselectivity. Products from this reaction, containing vicinal quaternary-tertiary stereogenic centers, are valuable synthetic intermediates and should find utility in alkaloid synthesis.
Authors: Courtney A. Luchaco-Cullis; Hirotake Mizutani; Kerry E. Murphy; Amir H. Hoveyda Journal: Angew Chem Int Ed Engl Date: 2001-04-17 Impact factor: 15.336