Synfacts 2008(2): 0163-0163  
DOI: 10.1055/s-2007-992443
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York

Mo-Catalyzed Allylic Alkylation of 3-Aryloxindoles

Contributor(s): Hisashi Yamamoto, Joshua Payette
B. Trost*, Y. Zhang
Stanford University, USA
Further Information

Publication History

Publication Date:
23 January 2008 (online)

Significance

The authors report a Mo-catalyzed allylic alkylation of 3-aryloxindoles to give branched products containing a quaternary carbon as well as a vicinal tertiary center. This system tolerates a wide array of aryl substituents on the oxindole ring. Furthermore, various functionalized electrophiles could be used in this reaction to give products in high diastereo- and enantioselectivities. Importantly, bond formation occurs at the more substituted position of the π-allyl, even with sterically demanding nucleophiles.