Catalytic Enantioselective Stereoablative Alkylation of 3-Halooxindoles: Facile Access to Oxindoles with C3 All-Carbon Quaternary Stereocenters
From 2 to 1! Racemic tertiary halooxindoles proceed to enantioenriched oxindoles bearing all-carbon quaternary stereocenters as a result of a catalytic enantioselective stereoablative process (see scheme). The application of this procedure allows for the rapid asymmetric construction of biologically significant alkaloid core motifs.
Additional Information© 2009 WILEY. Received: 1 June 2009. We wish to thank the California TRDRP (postdoctoral fellowships to X.H. and S.K.), Abbott Laboratories, Amgen, Merck, Bristol-Myers Squibb, Boehringer Ingelheim, the Gordon and Betty Moore Foundation, and Caltech for financial support. Lawrence Henling and Dr. Michael Day are gratefully acknowledged for X-ray crystallographic structure determination. Prof. David Horne is thanked for helpful discussions. The Bruker KAPPA APEX II X-ray diffractometer was purchased through an NSF CRIF:MU award to the California Institute of Technology, CHE-0639094. Dr. David VanderVelde and Dr. Scott Ross are acknowledged for NMR assistance.
Supplemental Material - sm001.pdf