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...

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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
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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
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cited_by cdi_FETCH-LOGICAL-a445t-76bf0b5615dfaa5edd304c43ad631b884e33a0ab23220c8b2be8599216681e333
cites cdi_FETCH-LOGICAL-a445t-76bf0b5615dfaa5edd304c43ad631b884e33a0ab23220c8b2be8599216681e333
container_end_page 7100
container_issue 21
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container_title Journal of organic chemistry
container_volume 69
creator Nakano, Hiroto
Takahashi, Kouichi
Okuyama, Yuko
Senoo, Chieko
Tsugawa, Natsumi
Suzuki, Yuichiro
Fujita, Reiko
Sasaki, Kazuo
Kabuto, Chizuko
description 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).
doi_str_mv 10.1021/jo049375j
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source American Chemical Society:Jisc Collections:American Chemical Society Read & Publish Agreement 2022-2024 (Reading list)
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
title Chiral Phosphinooxazolidine Ligands for Palladium- and Platinum-Catalyzed Asymmetric Diels−Alder Reactions
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