AI Article Synopsis
- Imine reductases (IREDs) are valuable for synthesizing chiral amines, with applications in asymmetric imine reduction and reductive aminations of aldehydes and ketones.
- The study discusses the reductive amination of various carbonyls and dicarbonyls using hydrazines, facilitated by the IRED from Myxococcus stipitatus.
- A hydrogenase cofactor regeneration system was incorporated to enhance scalability and efficiency of the process, showcasing the significant potential of IREDs in biocatalysis.
Article Abstract
Imine reductases (IREDs) provide promising opportunities for the synthesis of various chiral amines. Initially, asymmetric imine reduction was reported, followed by reductive aminations of aldehydes and ketones via imines. Herein we present the reductive amination of structurally diverse carbonyls and dicarbonyls with hydrazines (reductive hydrazination), catalyzed by the IRED from Myxococcus stipitatus. In analogy to IRED-catalyzed reductive aminations, various carbonyls and dicarbonyls could react with simple hydrazines to produce substituted acyclic and cyclic N-alkylhydrazines. By incorporating and scaling up a hydrogenase cofactor regeneration system, we demonstrated the scalability and atom-efficiency of an H-driven double reductive hydrazination, highlightling the potential of IREDs in biocatalysis.
Download full-text PDF |
Source |
|---|---|
| http://dx.doi.org/10.1002/cbic.202400700 | DOI Listing |
Publication Analysis
Top Keywords
Similar Publications
Nucleophilic Functionalization of a Cationic Pentaphosphole Complex - A Systematic Study of Reactivity.
Chemistry
January 2025
University of Regensburg, Inorganic Chemistry, Universitätsstrasse 31, D-93040, Regensburg, GERMANY.
The systematic nucleophilic functionalization of the cationic pentaphosphole ligand complex [Cp*Fe(η4-P5Me)][OTf] (A) with group 16/17 nucleophiles is reported. This method represents a highly reliable and versatile strategy for the design of novel transition-metal complexes featuring twofold substituted end-deck cyclo-P5 ligands, bearing unprecedented hetero-element substituents. By the reaction of A with classical group 16 nucleophiles, complexes of the type [Cp*Fe(η4-P5MeE)] (E = OEt (1), OtBu (2), SPh (3), SePh (4)) are obtained.
View Article and Find Full Text PDFAxially Chiral Phenanthroline Ligand-Enabled Pd-Catalyzed Asymmetric Amination and Alkylation of Aryl-Substituted Morita-Baylis-Hillman Adducts.
Org Lett
December 2024
Key Laboratory for Advanced Materials and Joint International Research Laboratory of Precision Chemistry and Molecular Engineering, Feringa Nobel Prize Scientist Joint Research Center, Frontiers Science Center for Materiobiology and Dynamic Chemistry, School of Chemistry and Molecular Engineering, East China University of Science & Technology, Shanghai 200237, China.
Highly enantioselective allylic amination and alkylation of racemic sterically hindered aryl-substituted Morita-Baylis-Hillman (MBH) adducts have been achieved by using an in situ formed Pd-catalyst from an axially chiral phenanthroline ligand. This dynamic kinetic asymmetric transformation (DYKAT) is compatible with cyclic and acyclic secondary amines, dialkyl malonates, β-keto esters, acetylacetone, and malononitrile, affording the corresponding chiral products, such as β-amino acid esters, in up to 95% yield and with up to a 99:1 enantiomeric ratio.
View Article and Find Full Text PDFStereoselective Enesulfinamide-Sulfinylimine Tautomerization of β,β-Disubstituted Enesulfinamides.
Org Lett
December 2024
School of Chemical Science and Technology, Yunnan University, Kunming, Yunnan 650091, China.
In the presence of cesium fluoride and organosilicon reagent, β,β-disubstituted NH-enesulfinamides undergo stereoselective enesulfinamide-sulfinylimine tautomerization at room temperature, resulting in the formation of α-branched -sulfinyl ketimines in good yields with high stereoselectivity. A variety of acyclic ketone surrogates α-substituted with two electronically and sterically similar groups (e.g.
View Article and Find Full Text PDFDiastereoselective Substitution Reactions of Acyclic Acetals Controlled by Remote Participation of an Acyloxy Group.
Org Lett
December 2024
Department of Chemistry, New York University, 100 Washington Square East, New York, New York 10003, United States.
A remote carbonyl group up to six atoms away from the acetal group can induce 1,2-asymmetric induction in nucleophilic substitution reactions of acyclic acetals. Isolation of a cyclic carbonate under Lewis acidic conditions and computational studies suggested that the remote carbonyl group participated through the formation of a cyclic dioxocarbenium ion intermediate. The stereochemical outcomes depended on the size of the alkyl substituent and that of the nucleophile employed.
View Article and Find Full Text PDFStereoselective Aminomethylation of β,β-Disubstituted Enesulfinamides: Asymmetric Construction of Less Accessible Acyclic α,α-Disubstituted α-Aminomethylated Ketimines.
J Org Chem
December 2024
School of Chemical Science and Technology, Yunnan University, Kunming, Yunnan 650091, China.
β,β-Disubstituted enesulfinamides undergo stereoselective nucleophilic addition to the formaldehyde imines, in situ formed from tosylmethylcarbamates, affording α-aminomethylated ketimines bearing a challenging acyclic quaternary stereocenter substituted by two sterically and electronically similar groups (e.g., Me and Et).
View Article and Find Full Text PDFWant AI Summaries of new PubMed Abstracts delivered to your In-box?
Enter search terms and have AI summaries delivered each week - change queries or unsubscribe any time!