A Chemo-Enzymatic Dearomatization Cascade Approach to Enantioenriched Piperidines from Pyridines DOI
Benjamin List, Mathias Turberg

Synfacts, Journal Year: 2023, Volume and Issue: 19(03), P. 0293 - 0293

Published: Feb. 13, 2023

Key words amine oxidase - ene-imine reductase chemo-enzymatic dearomatization piperidine synthesis

Language: Английский

Biocatalytic reductive aminations with NAD(P)H-dependent enzymes: enzyme discovery, engineering and synthetic applications DOI
Bo Yuan, Dameng Yang, Ge Qu

et al.

Chemical Society Reviews, Journal Year: 2023, Volume and Issue: 53(1), P. 227 - 262

Published: Dec. 7, 2023

This review summarized NAD(P)H-dependent amine dehydrogenases and imine reductases which catalyzes asymmetric reductive amination to produce optically active amines.

Language: Английский

Citations

28
Multifunctional Biocatalysts for Organic Synthesis DOI Creative Commons
Thomas W. Thorpe, James R. Marshall, Nicholas J. Turner

et al.

Journal of the American Chemical Society, Journal Year: 2024, Volume and Issue: 146(12), P. 7876 - 7884

Published: March 15, 2024

Biocatalysis is becoming an indispensable tool in organic synthesis due to high enzymatic catalytic efficiency as well exquisite chemo- and stereoselectivity. Some biocatalysts display great promiscuity including a broad substrate scope the ability catalyze more than one type of transformation. These promiscuous activities have been applied individually efficiently access numerous valuable target molecules. However, systems which enzymes possessing multiple different are less developed. Such multifunctional (MFBs) would simplify chemical by reducing number operational steps enzyme count, simplifying sequence space that needs be engineered develop efficient biocatalyst. In this Perspective, we highlight recently reported MFBs focusing on their synthetic utility mechanism. We also offer insight into origin comment potential strategies for discovery engineering.

Language: Английский

Citations

10
Imine Reductases and Reductive Aminases in Organic Synthesis DOI Creative Commons
Godwin A. Aleku

ACS Catalysis, Journal Year: 2024, Volume and Issue: unknown, P. 14308 - 14329

Published: Sept. 12, 2024

Language: Английский

Citations

9
Catalytic Enantioselective Synthesis of 3-Piperidines from Arylboronic Acids and Pyridine DOI Creative Commons
Sourabh Mishra, Sedef Karabıyıkoğlu, Stephen P. Fletcher

et al.

Journal of the American Chemical Society, Journal Year: 2023, Volume and Issue: 145(26), P. 14221 - 14226

Published: June 22, 2023

Piperidines are frequently found in natural products and of importance to the pharmaceutical industry. A generally useful asymmetric route enantiomerically enriched 3-substituted piperidines remains elusive. Here we report a cross-coupling approach enantioenriched 3-piperidines from pyridine- sp2-hybridized boronic acids. The key step involves Rh-catalyzed reductive Heck reaction aryl, heteroaryl, or vinyl acids phenyl pyridine-1(2H)-carboxylate provide tetrahydropyridines high yield excellent enantioselectivity with wide functional group tolerance. three-step process involving i) partial reduction pyridine, ii) carbometalation, then iii) another provides access variety 3-piperidines, including clinically used materials such as Preclamol Niraparib.

Language: Английский

Citations

15
Chemo-enzymatic synthesis of chiral 3-substituted tetrahydroquinolines by a sequential biocatalytic cascade and Buchwald–Hartwig cyclization DOI
Zefei Xu, Jinhui Feng, Peiyuan Yao

et al.

Green Chemistry, Journal Year: 2023, Volume and Issue: 25(12), P. 4667 - 4673

Published: Jan. 1, 2023

A one-pot bienzymatic cascade was developed to synthesize ( S )- N -(3-aryl-2-methylpropyl) prop-2-en-1-amines from α,β-unsaturated aldehydes, and 3-substituted tetrahydroquinolines were prepared via Buchwald–Hartwig amination deallylation.

Language: Английский

Citations

13
The Impact of Metagenomics on Biocatalysis DOI Creative Commons
Bethany N. Hogg, Christian Schnepel, James Finnigan

et al.

Angewandte Chemie International Edition, Journal Year: 2024, Volume and Issue: 63(21)

Published: March 18, 2024

Abstract In the ever‐growing demand for sustainable ways to produce high‐value small molecules, biocatalysis has come forefront of greener routes these chemicals. As such, need constantly find and optimise suitable biocatalysts specific transformations never been greater. Metagenome mining shown rapidly expand toolkit promiscuous enzymes needed new transformations, without requiring protein engineering steps. If is needed, metagenomic candidate can often provide a better starting point than previously discovered enzyme on open database or from literature, instance. this review, we highlight where metagenomics made substantial impact area in recent years. We review discovery unexplored ‘hidden’ sequence space, leading characterisation with enhanced properties that originate natural selection pressures native environments.

Language: Английский

Citations

5
Synthesis of Dihydropyridine Spirocycles by Semi-Pinacol-Driven Dearomatization of Pyridines DOI Creative Commons
Joseph C. Abell, Christian Paul Bold, Laia Vicens

et al.

Organic Letters, Journal Year: 2023, Volume and Issue: 25(2), P. 400 - 404

Published: Jan. 10, 2023

The identification of the beneficial pharmacokinetic properties aza-spirocycles has led to routine incorporation these highly rigid and three-dimensional structures in pharmaceuticals. Herein, we report an operationally simple synthesis spirocyclic dihydropyridines via electrophile-induced dearomative semi-pinacol rearrangement 4-(1'-hydroxycyclobutyl)pyridines. various points for diversification spirocyclization precursors, as well synthetic utility amine ketone functionalities products, provide potential rapidly assemble medicinally relevant spirocycles.

Language: Английский

Citations

12
Bifunctional Imine Reductase Cascades for the Synthesis of Saturated N-Heterocycles DOI Creative Commons
Jeremy I. Ramsden, Bruna Zucoloto da Costa, Rachel S. Heath

et al.

ACS Catalysis, Journal Year: 2024, Volume and Issue: 14(19), P. 14703 - 14710

Published: Sept. 19, 2024

Saturated

Language: Английский

Citations

4
Modular Construction of Chiral Aminopiperidine via Palladium-Catalyzed Hydroamination of 1,2-Dihydropyridine DOI
Qian Wang, Shouyou Huang,

Lifei Nie

et al.

Organic Letters, Journal Year: 2025, Volume and Issue: unknown

Published: Feb. 12, 2025

In this study, we describe a generally straightforward methodology for the catalytic synthesis of chiral aminopiperidine from pyridine and azoles. The key step was palladium-catalyzed regioselective N–H insertion into double bond 1,2-dihydropyridine. This hydroamination exhibits wide substrate scope functional group compatibility. Mechanistic study revealed that C═C followed cis addition. utility protocol demonstrated by diverse functionalization enamine bond.

Language: Английский

Citations

0
Chemoenzymatic two-step synthesis of tartaric acid employing glucose oxidase in combination with bimetallic AuPt/TiO2 catalyst DOI Creative Commons

Lanxue Li,

Mengyuan Liu, Yaru Yan

et al.

Green Synthesis and Catalysis, Journal Year: 2025, Volume and Issue: unknown

Published: March 1, 2025

Language: Английский

Citations

0