Noyori-Ikariya-type ruthenium(II)-catalysts for asymmetric transfer hydrogenation (ATH) have been known for 25 years and have proved as a well-behaved and user-friendly platform for the synthesis of chiral secondary alcohols. A progress has been made in the past five years in understanding the asymmetric reduction of complex ketones, where up to four stereocenters can be controlled in a single chemical transformation. Intriguing multi-chiral molecular architectures are therefore available in few well understood and robust synthetic steps from commercially available building blocks and possess handles for additional functionalization. The aim of this Review is to showcase the availability of three-dimensional scaffolds and homochiral lead-like compounds via ATH and inspire their direct use in drug discovery endeavors. Basic mechanistic insights are provided to demystify the stereo-chemical outcomes, as well as examples of diastereoselective transformations of enantiopure alcohols to give a feeling of how these rigid non-planar molecules can be further elaborated.

https://chemistry-europe.onlinelibrary.wiley.com/doi/pdf/10.1002/chem.202180162

Escaping from Flatland: Stereoconvergent Synthesis of Three-Dimensional Scaffolds via Ruthenium(II)-Catalyzed Noyori–Ikariya Transfer Hydrogenation

A catalytic protocol for the enantio- and diastereoselective reduction of α-substituted-β-keto carbonitriles is described The reaction involves a DKR-ATH process with the simultaneous construction of β-hydroxy carbonitrile scaffolds with two contiguous stereogenic centers A wide range of α-substituted-β-keto carbonitriles were obtained in high yields (94%-98%) and excellent enantio- and diastereoselectivities (up to >99% ee, up to >99:1 dr) The origin of the diastereoselectivity was also rationalized by DFT calculations Furthermore, this methodology offers rapid access to the pharmaceutical intermediates of Ipenoxazone and Tapentadol

Asymmetric Transfer Hydrogenation of α-Substituted-β-Keto Carbonitriles via Dynamic Kinetic Resolution.

Based on the ever-increasing demand for enantiomerically pure compounds, the development of efficient, atom-economical, and sustainable methods to produce chiral alcohols and amines is a major concern. Homogeneous asymmetric catalysis with transition-metal complexes including asymmetric hydrogenation (AH) and transfer hydrogenation (ATH) of ketones and imines through dynamic kinetic resolution (DKR) allowing the construction of up to three stereogenic centers is the main focus of the present short review, emphasizing the development of new catalytic systems combined to new classes of substrates and their applications as well. 1 	Introduction 2 	Asymmetric Hydrogenation via Dynamic Kinetic Resolution 2.1 	α-Substituted Ketones 2.2	α-Substituted β-Keto Esters and Amides 2.3 	α-Substituted Esters 2.4 	Imine Derivatives 3 	Asymmetric Transfer Hydrogenation via Dynamic Kinetic Resolution 3.1 	α-Substituted Ketones 3.2 	α-Substituted β-Keto Esters, Amides, and Sulfonamides 3.3 	α,β-Disubstituted Cyclic Ketones 3.4 	β-Substituted Ketones 3.5 	Imine Derivatives 4. 	Conclusion

Recent Progress and Applications of Transition-Metal-Catalyzed Asymmetric Hydrogenation and Transfer Hydrogenation of Ketones and Imines through Dynamic Kinetic Resolution

trans-Diastereoselective Ru(II)-Catalyzed Asymmetric Transfer Hydrogenation of α-Acetamido Benzocyclic Ketones via Dynamic Kinetic Resolution

Rhodium-mediated asymmetric transfer hydrogenation: a diastereo- and enantioselective synthesis of syn-α-amido β-hydroxy esters

Highly Enantioselective Synthesis of syn-β-Hydroxy α-Dibenzylamino Esters via DKR Asymmetric Transfer Hydrogenation and Gram-Scale Preparation of Droxidopa

A design of experiments (DoE) approach was applied to the development and optimization of the manufacturing process to prepare linagliptin. DoE techniques such as a central composite face-centered design and a fractional factorial design were applied to obtain the critical process parameters and establish the optimal reaction conditions. With process-related impurities determined and successfully removed, a robust high-yielding and high-purity procedure was identified, which has been successfully demonstrated at a 100 g scale level to prepare the desired product in a 68% overall isolated yield and high-performance liquid chromatography (HPLC) purity of around 99.9%. 

Process Development and Optimization of Linagliptin Aided by the Design of Experiments (DoE)

The present invention relates to a method for preparing a droxidopa intermediate (2S,3R)-3-(3,4-dibenzyloxyphenyl)-2-dibenzylamino-3-hydroxypropionate, comprising carrying out asymmetric hydrogenation to 3-(3,4-dibenzyloxyphenyl)-2-dibenzylamino-3-oxo-propionate in an organic solvent under the catalysis of a ruthenium catalyst in the presence of a hydrogen donor reagent and an organic base. The reaction highly stereoselectively introduces two chiral centres of droxidopa in a high yield in one step. Furthermore, on the basis of the reaction, a method for preparing droxidopa is designed. The method has a simple and short process, and can stereoselectively synthesize droxidopa.

Method for preparing droxidopa and intermediate thereof

Efficient Synthesis of a Key Intermediate for Moxifloxacin Via Intramolecular Double Stereodifferentiation

Process Development and Optimization of Apalutamide Synthesis Aided by the Design of Experiments (DoE)

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