The highly enantioselective Diels–Alder reaction of 1,2-dihydropyridine using chiral cationic palladium–phosphinooxazolidine catalyst for the synthesis of chiral isoquinuclidines

The DA reaction of 1-phenoxy-1,2-dihydropyridine with 1-substituted 2-acryloyl-pyrazolidin-3-ones using cationic chiral Pd–phosphinooxazolidine catalyst afforded chiral isoquinuclidines with an excellent optical purity (up to 97% ee). The enantioselective Diels–Alder reactions of 1-phenoxycarbonyl-1...

Full description

Saved in:
Bibliographic Details
Published in:Tetrahedron letters 2005-08, Vol.46 (34), p.5677-5681
Main Authors: Nakano, Hiroto, Tsugawa, Natsumi, Fujita, Reiko
Format: Article
Language:English
Subjects:
1,2-Dihydropyridine
Chiral cationic palladium–phosphinooxazolidine catalyst
Chiral isoquinuclidines
Enantioselective Diels–Alder reaction
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:The DA reaction of 1-phenoxy-1,2-dihydropyridine with 1-substituted 2-acryloyl-pyrazolidin-3-ones using cationic chiral Pd–phosphinooxazolidine catalyst afforded chiral isoquinuclidines with an excellent optical purity (up to 97% ee). The enantioselective Diels–Alder reactions of 1-phenoxycarbonyl-1,2-dihydropyridine with 1-alkylated acryloyl-pyrazolidin-3-ones using chiral cationic palladium–phosphinooxazolidine (Pd–POZ) catalyst afforded chiral isoquinuclidines with excellent enantioselectivity (up to 97% ee).
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2005.06.089