Pd-Catalyzed Asymmetric Allylic Etherification Using Chiral Biphenol-Based Diphosphinite Ligands and Its Application for The Formal Total Synthesis of (−)-Galanthamine

A library of novel chiral biphenol-based diphosphinite (BOP) ligands was designed and created. These BOP ligands were applied to a Pd-catalyzed intermolecular allylic etherification reaction, which provided a key intermediate for the formal total synthesis of (−)-galanthamine with 97% ee in 97% yiel...

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Bibliographic Details
Published in:Journal of organic chemistry 2013-04, Vol.78 (8), p.4013-4018
Main Authors: Zang, Yang, Ojima, Iwao
Format: Article
Language:English
Subjects:
Allyl Compounds - chemical synthesis
Allyl Compounds - chemistry
Catalysis
Galantamine - chemical synthesis
Galantamine - chemistry
Ligands
Molecular Structure
Palladium - chemistry
Phosphines - chemistry
Stereoisomerism
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Summary:A library of novel chiral biphenol-based diphosphinite (BOP) ligands was designed and created. These BOP ligands were applied to a Pd-catalyzed intermolecular allylic etherification reaction, which provided a key intermediate for the formal total synthesis of (−)-galanthamine with 97% ee in 97% yield.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo400355j