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Catalytic Enantioselective Stereoablative Alkylation of 3-Halooxindoles: Facile Access to Oxindoles with C3 All-Carbon Quaternary Stereocenters

Ma, Sandy and Han, Xiaoqing and Krishnan, Shyam and Virgil, Scott C. and Stoltz, Brian M. (2009) Catalytic Enantioselective Stereoablative Alkylation of 3-Halooxindoles: Facile Access to Oxindoles with C3 All-Carbon Quaternary Stereocenters. Angewandte Chemie International Edition, 48 (1). pp. 1-6. ISSN 1433-7851. https://resolver.caltech.edu/CaltechAUTHORS:20091002-090709845

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Abstract

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.


Item Type:Article
Related URLs:
URLURL TypeDescription
http://dx.doi.org/10.1002/anie.200902943 DOIArticle
http://www3.interscience.wiley.com/journal/122602862/abstractPublisherArticle
ORCID:
AuthorORCID
Virgil, Scott C.0000-0001-8586-5641
Stoltz, Brian M.0000-0001-9837-1528
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.
Funders:
Funding AgencyGrant Number
Abbott LaboratoriesUNSPECIFIED
AmgenUNSPECIFIED
Bristol-Myers SquibbUNSPECIFIED
Boehringer IngelheimUNSPECIFIED
Gordon and Betty Moore FoundationUNSPECIFIED
CaltechUNSPECIFIED
NSFCHE-0639094
Subject Keywords:alkylation; asymmetric catalysis; copper; enantioselectivity; umpolung
Issue or Number:1
Record Number:CaltechAUTHORS:20091002-090709845
Persistent URL:https://resolver.caltech.edu/CaltechAUTHORS:20091002-090709845
Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:16164
Collection:CaltechAUTHORS
Deposited By: Ruth Sustaita
Deposited On:06 Oct 2009 21:18
Last Modified:03 Oct 2019 01:08

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