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
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.
