Catalytic Strategies to Enantiopure Benzoins: Past and Future

Synthesis ◽  
2019 ◽  
Vol 52 (03) ◽  
pp. 353-364 ◽  
Author(s):  
Lorena De Luca ◽  
Antonio Mezzetti
Keyword(s):  
Kinetic Resolution ◽  
Aromatic Aldehydes ◽  
Short Review ◽  
Dynamic Kinetic Resolution ◽  
Enantiomerically Pure ◽  
Nucleophilic Carbenes ◽  
Economic Methods ◽  
Benzoin Condensation ◽  
Future Challenges ◽  
Metal Catalyzed

The catalytic strategies developed so far for the synthesis of enantiomerically pure benzoins are reviewed. Particular attention is given to their substrate scope and limitations. Finally, this short review highlights the advantages of more atom-economic methods that have been reported recently.1 Introduction2 Benzoin Condensation2.1 Nucleophilic Carbenes as Catalysts2.2 Homocondensation of Aromatic Aldehydes2.3 Cross-Benzoin Condensation2.4 Acyloin Condensation2.5 Biocatalytic Methods3 Organocatalytic Friedel–Crafts Reaction4 Oxidative Methods4.1 α-Hydroxylation of Ketones4.2 Ketohydroxylation of Alkenes4.3 Enantiospecific Oxidation of meso-Hydrobenzoins4.4 Kinetic Resolution of Racemic Hydrobenzoins4.5 Biocatalytic Dynamic Kinetic Resolution5 Asymmetric Hemireduction of Benzils5.1 Biocatalytic Reductions – A Brief Summary5.2 Piers Hydrosilylation of Benzils5.3 Photoreduction of Benzils to Benzoins5.4 Metal-Catalyzed Hemihydrogenation of Benzils6 Conclusion and Future Challenges

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

Synthesis ◽  
2020 ◽  
Vol 53 (01) ◽  
pp. 30-50
Author(s):  
Phannarath Phansavath ◽  
Virginie Ratovelomanana-Vidal ◽  
Ricardo Molina Betancourt ◽  
Pierre-Georges Echeverria ◽  
Tahar Ayad
Keyword(s):  
Transition Metal ◽  
Asymmetric Catalysis ◽  
Kinetic Resolution ◽  
Asymmetric Hydrogenation ◽  
Short Review ◽  
Transfer Hydrogenation ◽  
Dynamic Kinetic Resolution ◽  
Catalytic Systems ◽  
Keto Esters ◽  
Metal Catalyzed

AbstractBased 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 Introduction2 Asymmetric Hydrogenation via Dynamic Kinetic Resolution2.1 α-Substituted Ketones2.2 α-Substituted β-Keto Esters and Amides2.3 α-Substituted Esters2.4 Imine Derivatives3 Asymmetric Transfer Hydrogenation via Dynamic Kinetic Resolution3.1 α-Substituted Ketones3.2 α-Substituted β-Keto Esters, Amides, and Sulfonamides3.3 α,β-Disubstituted Cyclic Ketones3.4 β-Substituted Ketones3.5 Imine Derivatives4. Conclusion

Kinetic Resolution, Dynamic Kinetic Resolution and Asymmetric Desymmetrization by N-Heterocyclic Carbene Catalysis

Synthesis ◽  
2019 ◽  
Vol 51 (09) ◽  
pp. 1871-1891 ◽  
Author(s):  
Carmela De Risi ◽  
Olga Bortolini ◽  
Graziano Di Carmine ◽  
Daniele Ragno ◽  
Alessandro Massi
Keyword(s):  
Kinetic Resolution ◽  
Stereoselective Synthesis ◽  
Short Review ◽  
Heterocyclic Carbenes ◽  
Dynamic Kinetic Resolution ◽  
Asymmetric Transformations ◽  
Significant Interest ◽  
Stetter Reactions

N-Heterocyclic carbenes (NHCs) are now well-established organocatalysts for a large number of asymmetric and non-asymmetric transformations. In the last 15 years, there has been significant interest in using NHCs in kinetic resolution (KR), dynamic kinetic resolution (DKR) and asymmetric desymmetrization reactions for the stereoselective synthesis of enantioenriched compounds, with diverse substrates and activation modes being adopted to this end. This short review brings into focus the progress made on NHC-catalyzed KR, DKR, and asymmetric desymmetrization from 2004 until December 2018. The literature discussed in this article is classified on the basis of the type of reaction involving the NHC catalyst.1 Introduction2 Acylation Strategies2.1 O-Acylation2.2 N-Acylation2.3 C-Acylation3 Aldol-Acylation Processes4 Benzoin Reactions5 Stetter Reactions6 Miscellaneous Approaches7 Conclusion

ChemInform Abstract: Dynamic Kinetic Resolution of Homoallylic Alcohols: Application to the Synthesis of Enantiomerically Pure 5,6-Dihydropyran-2-ones and δ-Lactones.

ChemInform ◽  
2014 ◽  
Vol 45 (12) ◽  
pp. no-no
Author(s):  
Madeleine C. Warner ◽  
Grigory A. Shevchenko ◽  
Suzan Jouda ◽  
Krisztian Bogar ◽  
Jan-E. Baeckvall
Keyword(s):  
Kinetic Resolution ◽  
Dynamic Kinetic Resolution ◽  
Enantiomerically Pure ◽  
Homoallylic Alcohols

ChemInform Abstract: A Chemoenzymatic Approach to Enantiomerically Pure Amines Using Dynamic Kinetic Resolution: Application to the Synthesis of Norsertraline.

ChemInform ◽  
2009 ◽  
Vol 40 (29) ◽  
Author(s):  
Lisa K. Thalen ◽  
Dongbo Zhao ◽  
Jean-Baptiste Sortais ◽  
Jens Paetzold ◽  
Christine Hoben ◽  
...  
Keyword(s):  
Kinetic Resolution ◽  
Dynamic Kinetic Resolution ◽  
Enantiomerically Pure

scholarly journals Progress on the Stereoselective Synthesis of Chiral Molecules Based on Metal-Catalyzed Dynamic Kinetic Resolution of Alcohols with Lipases

Symmetry ◽  
2021 ◽  
Vol 13 (9) ◽  
pp. 1744
Author(s):  
Raffaella Ferraccioli
Keyword(s):  
Kinetic Resolution ◽  
Stereoselective Synthesis ◽  
Cascade Reactions ◽  
Allylic Alcohols ◽  
Chiral Molecules ◽  
Dynamic Kinetic Resolution ◽  
Multiple Bonds ◽  
One Pot ◽  
Synthetic Utility ◽  
Metal Catalyzed

Metal/lipase-combo catalyzed dynamic kinetic resolution (DKR) of racemic chiral alcohols is a general and practical process to obtain the corresponding enantiopure esters R with quantitative conversion. The use of known Ru-catalysts as well as newly developed homogeneous and heterogeneous metal catalysts (Fe, V) contributed to make the DKR process more sustainable and to expand the substrate scope of the reaction. In addition to classical substrates, challenging allylic alcohols, tertiary alcohols, C1-and C2-symmetric biaryl diols turned out to be competent substrates. Synthetic utility further emerged from the integration of this methodology into cascade reactions leading to linear/cyclic chiral molecules with high ee through the formation of multiple bonds, in a one-pot procedure.

One-pot synthesis of (R)-2-acetoxy-1-indanone from 1,2-indanedione combining metal catalyzed hydrogenation and chemoenzymatic dynamic kinetic resolution

2015 ◽  
Vol 5 (1) ◽  
pp. 150-160 ◽  
Author(s):  
Otto Långvik ◽  
Thomas Sandberg ◽  
Johan Wärnå ◽  
Dmitry Yu. Murzin ◽  
Reko Leino
Keyword(s):  
Kinetic Resolution ◽  
Dynamic Kinetic Resolution ◽  
One Pot ◽  
One Pot Synthesis ◽  
Metal Catalyzed

A heterogeneously catalyzed one-pot reaction for synthesis of (R)-2-acetoxy-1-indanone is described.

A Chemoenzymatic Approach to Enantiomerically Pure Amines Using Dynamic Kinetic Resolution: Application to the Synthesis of Norsertraline

2009 ◽  
Vol 15 (14) ◽  
pp. 3403-3410 ◽  
Author(s):  
Lisa K. Thalén ◽  
Dongbo Zhao ◽  
Jean-Baptiste Sortais ◽  
Jens Paetzold ◽  
Christine Hoben ◽  
...  
Keyword(s):  
Kinetic Resolution ◽  
Dynamic Kinetic Resolution ◽  
Enantiomerically Pure
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