Kinetic resolution of racemic disubstituted 1-pyrrolines via asymmetric reduction with a chiral titanocene catalyst

1994 ◽  
Vol 116 (20) ◽  
pp. 9373-9374 ◽  
Author(s):  
Alma Viso ◽  
Nancy E. Lee ◽  
Stephen L. Buchwald
Keyword(s):  
Kinetic Resolution ◽  
Asymmetric Reduction

Enantioselective Catalytic Methods for the Elaboration of Chiral Tetrahydro-β-carbolines and Related Scaffolds

Synthesis ◽  
2017 ◽  
Vol 49 (12) ◽  
pp. 2605-2620 ◽  
Author(s):  
Nicolas Glinsky-Olivier ◽  
Xavier Guinchard
Keyword(s):  
Kinetic Resolution ◽  
Asymmetric Reduction ◽  
Asymmetric Hydrogenation ◽  
Transfer Hydrogenation ◽  
Chiral Molecules ◽  
Chiral Phosphoric Acid ◽  
Hydrogenation Reactions ◽  
Synthetic Intermediates ◽  
Catalyzed Reactions

Tetrahydro-β-carbolines are important synthetic intermediates in the total synthesis of natural products and of compounds exhibiting strong bioactivities. Over the last decades, catalytic methods using chiral catalysts have been described for their synthesis. This review covers catalytic and enantioselective methods to access chiral tetrahydro-β-carbolines and their applications in the elaboration of complex chiral molecules.1 Introduction2 Asymmetric Reduction of Dihydro-β-carbolines2.1 Asymmetric Transfer Hydrogenation Reactions2.2 Asymmetric Hydrogenation Reactions2.3 Biocatalyzed Reduction of Dihydro-β-carbolines3 Organocatalyzed Pictet–Spengler Reactions3.1 Chiral Thiourea-Catalyzed Reactions3.2 Chiral Phosphoric Acid Catalyzed Reactions4 Pictet–Spengler Reactions of In Situ Generated Cyclic Iminiums5 Organocatalyzed Functionalization of Dihydro-β-carboliniums6 Organocatalyzed Alkylation of Tetrahydro-β-carbolines7 Biocatalyzed Dynamic Kinetic Resolution of Tetrahydro-β-carbolines8 Conclusion and Perspectives

An Efficient Stereoselective Total Synthesis of All Stereoisomers of the Antibiotic Thiamphenicol through Ruthenium-Catalyzed Asymmetric Reduction by Dynamic Kinetic Resolution

2015 ◽  
Vol 2015 (27) ◽  
pp. 5949-5958 ◽  
Author(s):  
Marc Perez ◽  
Pierre-Georges Echeverria ◽  
Elsa Martinez-Arripe ◽  
Mehdi Ez Zoubir ◽  
Ridha Touati ◽  
...  
Keyword(s):  
Total Synthesis ◽  
Kinetic Resolution ◽  
Asymmetric Reduction ◽  
Dynamic Kinetic Resolution

Building Complexity and Achieving Selectivity through Catalysis – Case Studies from the Pharmaceutical Pipeline

Synlett ◽  
2020 ◽  
Author(s):  
Jason S. Tedrow ◽  
Oliver R. Thiel ◽  
Matthew G. Beaver ◽  
Seb Caille ◽  
Robert P. Farrell ◽  
...  
Keyword(s):  
Kinetic Resolution ◽  
Process Development ◽  
Asymmetric Reduction ◽  
Scale Up ◽  
Transfer Hydrogenation ◽  
Process Chemistry ◽  
Reduction Strategies ◽  
Apelin Receptor ◽  
Enzymatic Desymmetrization ◽  
Molecular Complexity

The last decade of small-molecule process development has witnessed a trend of increasing molecular complexity for clinical candidates. The continued advance of novel catalytic methods and subsequent translation to efficient and scalable processes has enabled process chemists to overcome the challenges associated with increasing complexity. This Account highlights several examples from the process chemistry laboratories at Amgen.1 Introduction2 The Evolution of Molecular Complexity3 Catalysis as a Lever to Build Complexity4 Ru(II)-Catalyzed Dynamic Kinetic Resolution Enabling the Manufacture of AMG 2325 Application of Enzymatic Desymmetrization toward Scale-Up of the MCL-1 Inhibitor AMG 1766 Synthesis of Fucostatin 1: Catalytic Asymmetric Transfer Hydrogenation7 Manganese-Catalyzed Asymmetric Epoxidation To Prepare a Carfilzomib Intermediate8 Asymmetric Reduction Strategies: Novel Apelin Receptor Agonists and AMG 9869 Conclusions

scholarly journals Synthesis of acremines A, B and F and studies on the bisacremines

2019 ◽  
Vol 15 ◽  
pp. 2271-2276
Author(s):  
Nils Winter ◽  
Dirk Trauner
Keyword(s):  
Total Synthesis ◽  
Kinetic Resolution ◽  
Asymmetric Reduction ◽  
Asymmetric Total Synthesis

The acremines are a family of meroterpenoids isolated from fungi of the genus Acremonium. Here, we present the asymmetric total synthesis of acremine F which hinges on a modestly enantioselective dihydroxylation and a subsequent kinetic resolution via a highly selective asymmetric reduction. Chemoselective oxidation of acremine F gave access to acremines A and B. The dimerization of acremine F to bisacremine E was investigated but could not be achieved, shedding light on the formation of the acremine dimers in nature.

scholarly journals Highly Efficient Kinetic Resolution of Aryl-Alkenyl Alcohols by Ru-Catalyzed Hydrogen Transfer

Molecules ◽  
2021 ◽  
Vol 26 (24) ◽  
pp. 7475
Author(s):  
Yipeng You ◽  
Ming Yu Jin ◽  
Guanyu Tao ◽  
Xiangyou Xing
Keyword(s):  
Organic Synthesis ◽  
Hydrogen Transfer ◽  
Kinetic Resolution ◽  
Asymmetric Reduction ◽  
Building Blocks ◽  
Enantioselective Synthesis ◽  
Allylic Alcohols ◽  
Secondary Alcohols ◽  
Highly Efficient ◽  
Reduction Of Ketones

No matter through asymmetric reduction of ketones or kinetic resolution of secondary alcohols, enantioselective synthesis of the corresponding secondary alcohols is challenging when the two groups attached to the prochiral or chiral centers are spatially or electronically similar. For examples, dialkyl (sp3 vs. sp3), diaryl (sp2 vs. sp2), and aryl-alkenyl (sp2 vs. sp2) alcohols are difficult to produce with high enantioselectivities. By exploiting our recently developed Ru-catalysts of minimal stereogenicity, we reported herein a highly efficient kinetic resolution of aryl-alkenyl alcohols through hydrogen transfer. This method enabled such versatile chiral building blocks for organic synthesis as allylic alcohols, to be readily accessed with excellent enantiomeric excesses at practically useful conversions.

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