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

Rezensent(en):
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
 

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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Publikationsverlauf

Artikel online veröffentlicht:
16. August 2023

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