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Synfacts 2023; 19(09): 0905
DOI: 10.1055/s-0042-1752879
DOI: 10.1055/s-0042-1752879
Metals in Synthesis
The Overman Asymmetric Intramolecular Heck Reaction for the Synthesis of 3-Alkyl-3-Aryloxindoles
Dounay AB,
Hatanaka K,
Kodanko JJ,
Oestreich M,
Overman LE,
*,
Pfeifer LA,
Weiss MM.
University of California, Irvine, USA
Catalytic Asymmetric Synthesis of Quarternary Carbons Bearing Two Aryl Substituents. Enantioselective Synthesis of 3-Alkyl-3-Aryl Oxindoles by Catalytic Asymmetric Intramolecular Heck Reactions.
J. Am. Chem. Soc. 2003;
125: 6261-6271
DOI: 10.1021/ja034525d.
Catalytic Asymmetric Synthesis of Quarternary Carbons Bearing Two Aryl Substituents. Enantioselective Synthesis of 3-Alkyl-3-Aryl Oxindoles by Catalytic Asymmetric Intramolecular Heck Reactions.
J. Am. Chem. Soc. 2003;
125: 6261-6271
DOI: 10.1021/ja034525d.
Key words
all-carbon quaternary stereocenters - intramolecular Heck reaction - oxindoles - palladium catalysis
Significance
In 2003, Overman and co-workers disclosed a palladium(0)-catalyzed asymmetric intramolecular Heck cyclization to form oxindoles with an all-carbon quaternary stereocenter in high enantioselectivities.
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Comment
The synthesis of 3-alkyl-3-aryloxindoles by catalytic enantioselective Heck cyclization was implemented in the total synthesis of several natural products.
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Review
TA. B. Dounay, L. E. Overman Chem. Rev. 2003, 103, 2945–2964.
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Publication History
Article published online:
16 August 2023
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