Chiral Phosphinooxazolidine Ligands for Palladium- and Platinum-Catalyzed Asymmetric Diels−Alder Reactions

Cationic palladium (Pd)- and platinum (Pt)-phosphinooxazolidine catalysts 13a−c, 15a−d, 17a−c, and 19a−c were prepared from phosphinooxazolidine ligands 1−3, MCl2 (M = Pd and Pt), and counterions, and the activities of the catalysts in the asymmetric Diels−Alder (DA) reactions of cyclic or acyclic d...

Full description

Saved in:
Bibliographic Details
Published in:Journal of organic chemistry 2004-10, Vol.69 (21), p.7092-7100
Main Authors: Nakano, Hiroto, Takahashi, Kouichi, Okuyama, Yuko, Senoo, Chieko, Tsugawa, Natsumi, Suzuki, Yuichiro, Fujita, Reiko, Sasaki, Kazuo, Kabuto, Chizuko
Format: Article
Language:English
Subjects:
Catalysis
Catalysts: preparations and properties
Chemistry
Exact sciences and technology
General and physical chemistry
Heterocyclic compounds
Heterocyclic compounds with n hetero atom and also o and/or s, se, te hetero atoms
Organic chemistry
Preparations and properties
Theory of reactions, general kinetics. Catalysis. Nomenclature, chemical documentation, computer chemistry
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:Cationic palladium (Pd)- and platinum (Pt)-phosphinooxazolidine catalysts 13a−c, 15a−d, 17a−c, and 19a−c were prepared from phosphinooxazolidine ligands 1−3, MCl2 (M = Pd and Pt), and counterions, and the activities of the catalysts in the asymmetric Diels−Alder (DA) reactions of cyclic or acyclic dienes with imide dienophiles were investigated. These catalysts demonstrated high levels of catalytic activity. The cationic Pd−POZ complex 13c provided particularly excellent enantioselectivity (98% ee) in the DA reactions of cyclopentadiene with acryloyl-, crotonyl-, and fumaroyl-1,3-oxazolidin-2-ones (20a−c).
ISSN:0022-3263
1520-6904
DOI:10.1021/jo049375j