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

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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Veröffentlicht in:Angewandte Chemie (International ed.) 2009-01, Vol.48 (43), p.8037-8041
Hauptverfasser: Ma, Sandy, Han, Xiaoqing, Krishnan, Shyam, Virgil, Scott C, Stoltz, Brian M
Format: Artikel
Sprache:eng
Schlagworte:
Alkylation
asymmetric catalysis
Catalysis
copper
Copper - chemistry
Crystallography, X-Ray
enantioselectivity
Indoles - chemistry
Molecular Conformation
Stereoisomerism
umpolung
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Zusammenfassung: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.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.200902943