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...

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Bibliographic Details
Published in:	Angewandte Chemie (International ed.) Vol. 48; no. 43; pp. 8037 - 8041
Main Authors:	Ma, Sandy, Han, Xiaoqing, Krishnan, Shyam, Virgil, Scott C, Stoltz, Brian M
Format:	Journal Article
Language:	English
Published:	Weinheim Wiley-VCH Verlag 01-01-2009 WILEY‐VCH Verlag
Subjects:	Alkylation asymmetric catalysis Catalysis copper Copper - chemistry Crystallography, X-Ray enantioselectivity Indoles - chemistry Molecular Conformation Stereoisomerism umpolung
Online Access:	Get full text
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Summary:	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.
Bibliography:	http://dx.doi.org/10.1002/anie.200902943 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. ObjectType-Article-1 SourceType-Scholarly Journals-1 ObjectType-Feature-2 content type line 23
ISSN:	1433-7851 1521-3773
DOI:	10.1002/anie.200902943