β,β‐Disubstituted Alkan‐2‐ones from Propargylic Alcohols Combining a Meyer‐Schuster Rearrangement and Asymmetric Alkene Bioreduction DOI Creative Commons
Lorena Escot, Sergio González‐Granda, Daniel Méndez‐Sánchez

et al.

Advanced Synthesis & Catalysis, Journal Year: 2024, Volume and Issue: 366(22), P. 4737 - 4746

Published: Aug. 14, 2024

Abstract The combination of a gold(I) N‐heterocyclic carbene complex and an ene‐reductase (ERED) has made possible the synthesis enantiopure β,β‐disubstituted ketones in one‐pot concurrent approach. protocol consists Meyer‐Schuster rearrangement racemic propargylic tertiary alcohols using [1,3‐bis(2,6‐diisopropylphenyl)imidazol‐2‐ylidene]‐[bis(trifluoromethanesulfonyl)‐imide]gold(I) (IPrAuNTf 2 ), followed by asymmetric alkene reduction α,β‐unsaturated ketone intermediate Zymomonas mobilis ERED (NCR‐ERED). chemoenzymatic cascade was optimised with model substrate, where E / Z ‐isomers both generated ( R )‐ketone, which rationalised silico molecular docking experiments. then applied towards production series )‐4‐substituted‐alkan‐2‐ones form straightforward manner.

Language: Английский

Dual Catalysis in Organic Synthesis: Current Challenges and New Trends DOI
Chandi C. Malakar, Luca Dell’Amico, Wanbin Zhang

et al.

European Journal of Organic Chemistry, Journal Year: 2022, Volume and Issue: 26(1)

Published: Dec. 9, 2022

Abstract Dual catalysis is one of the most powerful strategies for development chemical reactions in organic synthesis. This strategy can be divided into cooperative catalysis, relay and sequential according to actual mode operation communication between catalysts. In recent years, such has been applied a large number studies since it advantages of: 1) increasing reactivity enabling challenging transformations; 2) offering way controlling stereoselectivity asymmetric reactions, which traditional catalytic systems; 3) catalyze stereodivergent synthesis molecules bearing or more stereocenters from same starting materials. Perspective, intends introduce reader EurJOC special collection on Catalysis , aims summarize different categories dual demonstrate their benefits constructing new bonds selective manner. Finally, current challenges trends will also presented.

Language: Английский

Citations

57
Chemoenzymatic Cascades Combining Biocatalysis and Transition Metal Catalysis for Asymmetric Synthesis DOI Creative Commons
Sergio González‐Granda, Lorena Escot, Iván Lavandera

et al.

Angewandte Chemie International Edition, Journal Year: 2023, Volume and Issue: 62(18)

Published: Feb. 6, 2023

Abstract The combination of catalytic methods provides multiple advantages in organic synthesis, allowing access to diverse molecules a straightforward manner. Merging metal and enzyme catalysis is currently receiving great attention due the possibility assemble C−C coupling, olefin metathesis, hydration other reactions with exquisite stereospecificity displayed by enzymes. Thus, this minireview organized based on action species (Pd, Ru, Au, Ir, Fe…) different Special will be paid design sequential processes concurrent cascades, presenting solutions such as use surfactants or compartmentalization strategies for those cases where incompatibilities could hamper overall process.

Language: Английский

Citations

40
One-pot chemo- and photo-enzymatic linear cascade processes DOI Creative Commons
J. M. Carceller, Karen S. Arias, María J. Climent

et al.

Chemical Society Reviews, Journal Year: 2024, Volume and Issue: 53(15), P. 7875 - 7938

Published: Jan. 1, 2024

This review explores linear cascade reactions by combining chemo-, photo- and biocatalysts for organic synthesis strategies to overcome incompatibility issues.

Language: Английский

Citations

12
A Chemoenzymatic Cascade Combining a Hydration Catalyst with an Amine Dehydrogenase: Synthesis of Chiral Amines DOI
Fengwei Chang, Chengyi Wang, Qipeng Chen

et al.

Angewandte Chemie International Edition, Journal Year: 2021, Volume and Issue: 61(10)

Published: Dec. 22, 2021

The combination of biocatalysis and transition-metal catalysis can complement synthetic gaps only in a chemical or biological process. However, the intrinsic mutual deactivation between enzymatic species is significant challenge single operation. To address above issue, we developed an encapsulated Au/carbene combined with free amine dehydrogenase as co-catalyst system that enables efficient hydration/amination enantioselective cascade process to be accomplished. mechanistic investigation discloses dual comprised alkyne hydration, followed by reductive amination

Language: Английский

Citations

30
Chemoenzymatic Cascades Combining Biocatalysis and Transition Metal Catalysis for Asymmetric Synthesis DOI Creative Commons
Sergio González‐Granda, Lorena Escot, Iván Lavandera

et al.

Angewandte Chemie, Journal Year: 2023, Volume and Issue: 135(18)

Published: Feb. 6, 2023

Abstract The combination of catalytic methods provides multiple advantages in organic synthesis, allowing access to diverse molecules a straightforward manner. Merging metal and enzyme catalysis is currently receiving great attention due the possibility assemble C−C coupling, olefin metathesis, hydration other reactions with exquisite stereospecificity displayed by enzymes. Thus, this minireview organized based on action species (Pd, Ru, Au, Ir, Fe…) different Special will be paid design sequential processes concurrent cascades, presenting solutions such as use surfactants or compartmentalization strategies for those cases where incompatibilities could hamper overall process.

Language: Английский

Citations

10
Merging Gold(I) Catalysis with Amine Transaminases in Cascade Catalysis: Chemoenzymatic Transformation of Propargylic Alcohols into Enantioenriched Allylic Amines DOI
Sergio González‐Granda, Nikolaos V. Tzouras, Steven P. Nolan

et al.

Advanced Synthesis & Catalysis, Journal Year: 2022, Volume and Issue: 364(22), P. 3856 - 3866

Published: Oct. 3, 2022

Abstract The compatibility between gold(I) catalysts and amine transaminases has been explored to transform racemic propargylic alcohols into enantioenriched allylic amines in a straightforward selective manner. synthetic approach consists of gold(I)‐catalysed Meyer‐Schuster rearrangement series 2‐arylpent‐3‐yn‐2‐ols subsequent stereoselective enzyme‐catalysed transamination the resulting α,β‐unsaturated prochiral ketones. design cascade processes involving sequential or concurrent approaches studied our search for ideal reaction conditions produce desired amines. Thus, N‐heterocyclic carbene complex [1,3‐bis(2,6‐diisopropylphenyl)imidazol‐2‐ylidene]‐[bis(trifluoromethanesulfonyl)‐imide]gold(I) ([Au(IPr)(NTf 2 )] ( A ) aqueous medium was found be an catalyst, while selective, made‐in‐house commercial permitted asymmetric synthesis both E )‐4‐arylpent‐3‐en‐2‐amine enantiomers good isolated yields (53–84%) excellent stereoselectivities (97 >99% enantiomeric excess). magnified image

Language: Английский

Citations

16
Gold and Biocatalysis for the Stereodivergent Synthesis of Nor(pseudo)ephedrine Derivatives: Cascade Design Toward Amino Alcohols, Diols, and Diamines DOI Creative Commons
Sergio González‐Granda, Georg Steinkellner, Karl Gruber

et al.

Advanced Synthesis & Catalysis, Journal Year: 2023, Volume and Issue: 365(7), P. 1036 - 1047

Published: March 2, 2023

Abstract The combination of gold(I) and enzyme catalysis has provided access to a series nor(pseudo)ephedrine derivatives in regio‐ stereoselective manner. approach involves developing IPrAuNTf 2 ‐catalyzed hydration 1‐phenylprop‐2‐yn‐1‐yl acetate or N ‐(1‐phenylprop‐2‐yn‐1‐yl)acetamide, followed by (dynamic) asymmetric biotransamination bioreduction the corresponding keto ester amide intermediates. Enzyme actions were completely selective towards modification methyl ketones highly manner, allowing synthesis enantio‐ diastereomerically enriched products using either racemic optically active starting materials. Thus, amino alcohol, diol, diamine produced from propargyl esters amides (57 86% isolated yield), biocatalyst choice determining (stereo)selectivity overall cascade process (70–99% diastereomeric excess >98% enantiomeric excess), providing compounds straightforward magnified image

Language: Английский

Citations

8
A Chemoenzymatic Cascade Combining a Hydration Catalyst with an Amine Dehydrogenase: Synthesis of Chiral Amines DOI
Fengwei Chang, Chengyi Wang, Qipeng Chen

et al.

Angewandte Chemie, Journal Year: 2021, Volume and Issue: 134(10)

Published: Dec. 22, 2021

Abstract The combination of biocatalysis and transition‐metal catalysis can complement synthetic gaps only in a chemical or biological process. However, the intrinsic mutual deactivation between enzymatic species is significant challenge single operation. To address above issue, we developed an encapsulated Au/carbene combined with free amine dehydrogenase as co‐catalyst system that enables efficient hydration/amination enantioselective cascade process to be accomplished. mechanistic investigation discloses dual comprised alkyne hydration, followed by reductive amination

Language: Английский

Citations

5
β,β‐Disubstituted Alkan‐2‐ones from Propargylic Alcohols Combining a Meyer‐Schuster Rearrangement and Asymmetric Alkene Bioreduction DOI Creative Commons
Lorena Escot, Sergio González‐Granda, Daniel Méndez‐Sánchez

et al.

Advanced Synthesis & Catalysis, Journal Year: 2024, Volume and Issue: 366(22), P. 4737 - 4746

Published: Aug. 14, 2024

Abstract The combination of a gold(I) N‐heterocyclic carbene complex and an ene‐reductase (ERED) has made possible the synthesis enantiopure β,β‐disubstituted ketones in one‐pot concurrent approach. protocol consists Meyer‐Schuster rearrangement racemic propargylic tertiary alcohols using [1,3‐bis(2,6‐diisopropylphenyl)imidazol‐2‐ylidene]‐[bis(trifluoromethanesulfonyl)‐imide]gold(I) (IPrAuNTf 2 ), followed by asymmetric alkene reduction α,β‐unsaturated ketone intermediate Zymomonas mobilis ERED (NCR‐ERED). chemoenzymatic cascade was optimised with model substrate, where E / Z ‐isomers both generated ( R )‐ketone, which rationalised silico molecular docking experiments. then applied towards production series )‐4‐substituted‐alkan‐2‐ones form straightforward manner.

Language: Английский

Citations

0