Journal ArticleDOI
From a chiral switch to a ligand portfolio for asymmetric catalysis.
Reads0
Chats0
TLDR
The development of an enantioselective manufacturing process for ( S)-metolachlor, the active ingredient of the grass herbicide Dual Magnum, is described, and the Ir-Xyliphos hydrogenation catalyst achieves unprecedented 2 millions turnovers.Abstract:
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.read more
Citations
More filters
Journal ArticleDOI
Chiral Amine Synthesis – Recent Developments and Trends for Enamide Reduction, Reductive Amination, and Imine Reduction
TL;DR: The review examines the chiral amine literature from 2000-2009 concerning enantioselective and diastereoselectives methods for N-acylenamide and enamine reduction, reductive amination, and imine reduction.
Journal ArticleDOI
Iron- and Cobalt-Catalyzed Alkene Hydrogenation: Catalysis with Both Redox-Active and Strong Field Ligands
TL;DR: The hydrogenation of alkenes is one of the most impactful reactions catalyzed by homogeneous transition metal complexes finding application in the pharmaceutical, agrochemical, and commodity chemical industries and development of reliable, readily accessible cobalt precursors facilitated catalyst discovery.
Journal ArticleDOI
Industrial applications of immobilized enzymes—A review
Alessandra Basso,Simona Serban +1 more
TL;DR: A series of large-scale applications of immobilized enzymes with benefits for the food, chemical, pharmaceutical, cosmetics and medical device industries, some of which have been scarcely reported on previously are presented.
Journal ArticleDOI
The Growing Impact of Catalysis in the Pharmaceutical Industry
TL;DR: In this article, a number of selected, noteworthy industrial examples are discussed to showcase the catalytic technologies that have been successfully practiced on large scales for active pharmaceutical ingredient (API) synthesis.
References
More filters
Journal ArticleDOI
New Chiral Diphosphine Ligands Designed to have a Narrow Dihedral Angle in the Biaryl Backbone
Takao Saito,Tohru Yokozawa,Takero Ishizaki,Takashi Moroi,Noboru Sayo,Takashi Miura,Hidenori Kumobayashi +6 more
TL;DR: A series of optically active diphosphine ligands, (4,4′-bi-1,3-benzodioxole)-5,5′-diylbis(diarylphosphine)s (6), which are called SEGPHOS, has been designed and synthesized with dihedral angles in the Ru complexes being less than that in the corresponding BINAP-Ru complex as mentioned in this paper.
Journal ArticleDOI
Modular Phospholane Ligands in Asymmetric Catalysis
TL;DR: This Account outlines the preparation and application of a class of phosphine ligands based upon the trans-2,5-disubstituted phospholane moiety and highlights the versatility of highly efficient bis(phospholane)rhodium catalysts that allow enantioselective hydrogenation to produce a diverse range of compounds containing C-N, C-O, and C-C stereogenic centers.
Journal ArticleDOI
Solvias Josiphos Ligands: From Discovery to Technical Applications
TL;DR: The case history of the Solvias Josiphos ligands is described in this article, followed by a description of the family and their technical synthesis, and the catalytic performance of various Josiphosa metal complexes in model reactions and in real world synthetic applications are summarized.
Journal ArticleDOI
Catalytic Enantioselective Conjugate Reduction of Lactones and Lactams
TL;DR: Good to excellent yields and enantioselectivities were realized using a catalyst generated in situ from CuCl(2)O, t-BuONa, p-tol-BINAP, and PMHS, and this methodology was applied to the synthesis of (-)-Paroxetine.
Journal ArticleDOI
New developments in enantioselective hydrogenation
Rudolf Schmid,Emil Albin Broger,Marco Cereghetti,Yvo Crameri,Joseph Foricher,Michel Lalonde,R. K. Müller,M. Scalone,G. Schoettel,Ulrich Zutter +9 more
TL;DR: A broad variety of atropisomeric biphenyl diphosphines have been synthesized via optically active 6,6'-dimethoxybiphenyl-2,2'-diyl-bis(diphhenyl phosphonates), -bis@hosphonic dichlorides, -bis(phosphonous dichloride) and-bis@rimary diphophosphines as discussed by the authors.