Phase-transfer-catalyzed enantioselective α-alkylation of aryl acetates DOI

Yinuo Xiao,

Zhenpeng Li, Changming Xu

et al.

Tetrahedron Letters, Journal Year: 2024, Volume and Issue: unknown, P. 155347 - 155347

Published: Oct. 1, 2024

Language: Английский

Copper-catalyzed asymmetric cascade diyne cyclization/Meinwald rearrangement DOI

Ji‐Jia Zhou,

Li‐Gao Liu, Zhentao Zhang

et al.

Chinese Chemical Letters, Journal Year: 2025, Volume and Issue: unknown, P. 110870 - 110870

Published: Jan. 1, 2025

Language: Английский

Citations

0
Continuous-flow chemoenzymatic enantioselective synthesis of chiral β-nitroalcohols DOI

He Bing,

Chen Huang, Liya Zhou

et al.

Molecular Catalysis, Journal Year: 2025, Volume and Issue: 580, P. 115053 - 115053

Published: April 17, 2025

Language: Английский

Citations

0
Enzyme immobilization in a Ru(N^N)3-modified covalent organic framework for photoenzymatic cascade catalysis DOI
Yanxia Wang, Bingchen Guo, Zhihua Chai

et al.

Journal of Materials Chemistry A, Journal Year: 2024, Volume and Issue: 12(29), P. 18537 - 18543

Published: Jan. 1, 2024

A covalent organic framework integrated photocatalysis, cofactor regeneration, and enzyme catalysis, forging a photobiocatalytic platform for producing enantiomerically pure 1-(propylthio)pentan-3-ol.

Language: Английский

Citations

2
Engineering Styrene Oxide Isomerase Towards Enhanced Chemoenzymatic Synthesis of (S)‐Flurbiprofen DOI
Willy W. L. See, Joel P. S. Choo, Lei Du

et al.

Advanced Synthesis & Catalysis, Journal Year: 2024, Volume and Issue: 366(13), P. 2967 - 2975

Published: April 26, 2024

Abstract The conventional synthesis of ( S )‐flurbiprofen, a valuable non‐steroidal anti‐inflammatory drug (NSAID), involves inefficient chiral resolution with low‐yielding multiple reaction steps, or asymmetric low enantioselectivity and/or regioselectivity. Here, we developed high‐yielding, enantioselective, and sustainable )‐flurbiprofen via two chemoenzymatic approaches from simple alkene: (A) enzymatic epoxidation‐isomerization‐oxidation cascade Pd‐catalyzed arylation; (B) chemical epoxidation, isomerization‐oxidation cascade, arylation. Styrene oxide isomerase (SOI)‐catalyzed enantio‐retentive Meinwald rearrangement was the key step in pathways, but SOI suffers activity. engineered rounds iterative saturation mutagenesis screening three‐enzyme assay, generating double‐mutant DM (N99A/D95A) 5.5‐fold improvement catalytic efficiency k cat / K M ). In Pathway A, biotransformation 3‐fluoro‐4‐bromo‐α‐methylstyrene E. coli strain expressing , styrene monooxygenase (SMO) aldehyde dehydrogenase (ALDH), subsequent arylation afforded 98% yield 91% ee . B, epoxidation (Sharpless dihydroxylation ring‐closing), conversion using an ALDH NADH oxidase (NOX), produced 83% Compared to synthesis, methods reduced minimized waste generation improved overall yield.

Language: Английский

Citations

1
Phase-transfer-catalyzed enantioselective α-alkylation of aryl acetates DOI

Yinuo Xiao,

Zhenpeng Li, Changming Xu

et al.

Tetrahedron Letters, Journal Year: 2024, Volume and Issue: unknown, P. 155347 - 155347

Published: Oct. 1, 2024

Language: Английский

Citations

0