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Synfacts 2023; 19(09): 0905
DOI: 10.1055/s-0042-1752879
Metals in Synthesis

The Overman Asymmetric Intramolecular Heck Reaction for the Synthesis of 3-Alkyl-3-Aryloxindoles

Authors

    Contributor(s):

  • Martin Oestreich

  • Hendrik F. T. Klare

  • Phillip Pommerening

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
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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.


 

Comment

The synthesis of 3-alkyl-3-aryloxindoles by catalytic enantioselective Heck cyclization was implemented in the total synthesis of several natural products.


 

Review

TA. B. Dounay, L. E. Overman Chem. Rev. 2003, 103, 2945–2964.


 

 

Publication History

Article published online:
16 August 2023

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