From a Chiral Switch to a Ligand Portfolio for Asymmetric Catalysis

This Account is divided into two sections. In the first section, the development of an enantioselective manufacturing process for (S)-metolachlor, the active ingredient of the grass herbicide Dual Magnum, is described. This is today’s largest application of asymmetric catalysis, and the Ir-Xyliphos...

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Bibliographic Details
Published in:Accounts of chemical research 2007-12, Vol.40 (12), p.1240-1250
Main Authors: Blaser, Hans-Ulrich, Pugin, Benoît, Spindler, Felix, Thommen, Marc
Format: Article
Language:English
Subjects:
Acetamides - chemistry
Catalysis
Ligands
Phosphines - chemistry
Phosphorus - chemistry
Stereoisomerism
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Summary:This Account is divided into two sections. In the first section, the development of an enantioselective manufacturing process for (S)-metolachlor, the active ingredient of the grass herbicide Dual Magnum, is described. This is today’s largest application of asymmetric catalysis, and the Ir-Xyliphos hydrogenation catalyst achieves unprecedented 2 millions turnovers. The development started in 1982 and ended when the first production batch was run in November 1996. The strategies and approaches used for attaining the elusive goal are described, and the lessons learned are discussed. In the second section, the development and performance of a portfolio of chiral diphosphines for industrial asymmetric applications are described. Central to the portfolio is the idea of modular ligand families, i.e., diphosphines with the same backbone, where steric and electronic properties are easily tuned by the choice of the substituents at the phosphorous atoms.
ISSN:0001-4842
1520-4898
DOI:10.1021/ar7001057