Biocatalytic Formal Asymmetric para-Aminoethylation of Unprotected Phenols to Chiral Amines DOI
Jingqi Zhang, Xuan Deng, Xue Han

et al.

ACS Catalysis, Journal Year: 2024, Volume and Issue: 15(1), P. 81 - 90

Published: Dec. 13, 2024

Enantiomerically pure amines are vital for the development of biologically active compounds in medicine and agriculture. While aminoalkylation phenols is well-established creating nitrogen-containing frameworks, regio- stereoselective para-aminoethylation unprotected underexplored. To fill this gap, we propose a one-pot cascade biocatalysis system asymmetric into chiral amines, using simple pyruvate, NH4Cl, D/l-alanine as starting materials. Utilizing modular approach, successfully performed through sequential process vinylation hydroamination, achieving good conversions (51.0–72.0%) >99% ee both enantiomers amines. Additionally, biobased p-hydroxycinnamic acid l-tyrosine their derivatives were converted with moderate to (39.4–87%) integrating decarboxylation/hydroamination deamination-decarboxylation/hydroamination. This marks successful de novo biosynthesis method formal phenols.

Language: Английский

Csp2–H functionalization of phenols: an effective access route to valuable materials via Csp2–C bond formation DOI Creative Commons

Giulia Brufani,

Benedetta Di Erasmo,

Chao‐Jun Li

et al.

Chemical Science, Journal Year: 2024, Volume and Issue: 15(11), P. 3831 - 3871

Published: Jan. 1, 2024

In the vast majority of top-selling pharmaceutical and industrial products, phenolic structural motifs are highly prevalent. Non-functionalized simple phenols serve as building blocks in synthesis value-added chemicals. It is worth mentioning that lignin, being largest renewable biomass source aromatic nature, mainly consists units, which enable production structurally diverse phenols. Given their remarkable applicability chemical value chain, many efforts have been devoted to increasing molecular complexity scaffold. Among key techniques, direct functionalization Csp

Language: Английский

Citations

6
Brønsted Acid‐Catalyzed Enantioselective and para‐Selective Addition of Phenols to 1‐Alkynylnaphth‐2‐ols DOI Creative Commons
Anjali Dahiya,

Kalyan Dhara,

Jordan Garo

et al.

Advanced Synthesis & Catalysis, Journal Year: 2025, Volume and Issue: unknown

Published: Jan. 22, 2025

Abstract A chiral Brønsted acid‐catalyzed synthesis of axially alkenes was developed via an enantioselective and para ‐selective Friedel–Crafts reaction between phenols 1‐alkynylnaphth‐2‐ols. This methodology features efficient hydroarylation with high functional group tolerance, complete ‐selectivity, excellent yields (up to 99%), enantioselectivities 94% ee) in the presence a N ‐triflylphosphoramide catalyst. DFT calculations were performed investigate ‐selectivity results indicate that both kinetics thermodynamics parameters are more favorable compared ortho ‐selectivity.

Language: Английский

Citations

0
Nickel-Catalyzed One-Pot H/D Exchange and Asymmetric Michael Addition in the Presence of D2O DOI

Junyu Zhou,

Yuxiang Zhang, Jing Zhou

et al.

The Journal of Organic Chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: March 24, 2025

A step-economical and efficient strategy for the enantioselective synthesis of tetradeuterated γ-nitroketones using a cost-effective readily available deuterium source is highly desirable. Herein, we report nickel-catalyzed one-pot H/D exchange Michael addition α,β-unsaturated 2-acyl imidazoles with nitromethane in presence D2O. This protocol demonstrates excellent efficiency, high enantioselectivity, broad substrate scope, offering practical versatile approach to accessing deuterium-labeled compounds.

Language: Английский

Citations

0
Asymmetric catalytic Friedel–Crafts alkylation with arenes and heteroarenes: construction of 3,3-disubstituted oxindoles DOI

Tinghui Zhang,

Ziwei Zhong,

Zi Zeng

et al.

Organic Chemistry Frontiers, Journal Year: 2023, Volume and Issue: 10(20), P. 5274 - 5283

Published: Jan. 1, 2023

The asymmetric Friedel–Crafts alkylation of 3-bromo-3-substituted oxindoles with arenes and heteroarenes was achieved to synthesize enantioenriched C3-arylated oxindoles.

Language: Английский

Citations

9
Synthesis of N-triflyl aldimines catalyzed by imino-λ3-iodane DOI

Shun Sunagawa,

Yoko Tezuka,

Akira Tsubouchi

et al.

Organic Chemistry Frontiers, Journal Year: 2024, Volume and Issue: 11(17), P. 4716 - 4721

Published: Jan. 1, 2024

Imino-λ 3 -iodane, conventionally used as a nitrene donor in nitrogen functionalization, is involved dehydrative condensation an acid–base cooperative catalyst.

Language: Английский

Citations

0
Biocatalytic Formal Asymmetric para-Aminoethylation of Unprotected Phenols to Chiral Amines DOI
Jingqi Zhang, Xuan Deng, Xue Han

et al.

ACS Catalysis, Journal Year: 2024, Volume and Issue: 15(1), P. 81 - 90

Published: Dec. 13, 2024

Enantiomerically pure amines are vital for the development of biologically active compounds in medicine and agriculture. While aminoalkylation phenols is well-established creating nitrogen-containing frameworks, regio- stereoselective para-aminoethylation unprotected underexplored. To fill this gap, we propose a one-pot cascade biocatalysis system asymmetric into chiral amines, using simple pyruvate, NH4Cl, D/l-alanine as starting materials. Utilizing modular approach, successfully performed through sequential process vinylation hydroamination, achieving good conversions (51.0–72.0%) >99% ee both enantiomers amines. Additionally, biobased p-hydroxycinnamic acid l-tyrosine their derivatives were converted with moderate to (39.4–87%) integrating decarboxylation/hydroamination deamination-decarboxylation/hydroamination. This marks successful de novo biosynthesis method formal phenols.

Language: Английский

Citations

0