Enantioselective synthesis of 3,3-disubstituted oxindoles through Pd-catalyzed cyanoamidation

Yoshizumi Yasui; Haruhi Kamisaki; Yoshiji Takemoto

doi:10.1021/ol801168j

Enantioselective synthesis of 3,3-disubstituted oxindoles through Pd-catalyzed cyanoamidation

Org Lett. 2008 Aug 7;10(15):3303-6. doi: 10.1021/ol801168j. Epub 2008 Jun 27.

Authors

Yoshizumi Yasui¹, Haruhi Kamisaki, Yoshiji Takemoto

Affiliation

¹ Graduate School of Pharmaceutical Sciences, Kyoto University, Yoshida, Sakyo-ku, Kyoto 606-8501, Japan.

PMID: 18582078
DOI: 10.1021/ol801168j

Abstract

The first enantioselective cyanoamidation of olefins provides quick access to a variety of 3,3-disubstituted oxindoles. The combination of Pd(dba)2, an optically active phosphoramidite, and N, N-dimethylpropylene urea (DMPU) in decalin were found to be the best conditions.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Amination
Aniline Compounds / chemistry
Catalysis
Cyclization
Indoles / chemical synthesis*
Indoles / chemistry
Nitriles / chemistry
Oxindoles
Palladium / chemistry
Stereoisomerism

Substances

Aniline Compounds
Indoles
Nitriles
Oxindoles
2-oxindole
Palladium