Siriphong Somprasong

University of Groningen

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i-10 index

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Marta Castiñeira Reis

Center for Research in Molecular Medicine and Chronic Diseases

Syuzanna R. Harutyunyan

University of Groningen

Torsak Luanphaisarnnont

Mahidol University

Watcharapon Prasitwatcharakorn

Mahidol University

Baonian Wan

Chinese Academy of Sciences

Juana M. Pérez

University of Almería

Peerawat Saejong

Imperial College London

Chaiwat Rujirasereesakul

Mahidol University

Cooperative Institutions

Mahidol University

University of Groningen

Rijksmuseum

Imperial College London

University of Manchester

Center for Research in Molecular Medicine and Chronic Diseases

Universidade de Santiago de Compostela

Universidade de Vigo

University of California, Davis

Chinese Academy of Sciences

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Catalytic Access to Chiral δ‐Lactams via Nucleophilic Dearomatization of Pyridine Derivatives

Angewandte Chemie (2022)

Siriphong Somprasong Marta Castiñeira Reis Syuzanna R. Harutyunyan

Abstract Nitrogen‐bearing rings are common features in the molecular structures of modern drugs, with chiral δ ‐lactams being an important subclass due to their known pharmacological properties. Catalytic dearomatization of preactivated pyridinium ion derivatives emerged as a powerful method for the rapid construction of chiral N ‐heterocycles. However, direct catalytic dearomatization of simple pyridine derivatives are scarce and methodologies yielding chiral δ ‐lactams are yet to be developed. Herein, we describe an enantioselective C4‐dearomatization of methoxypyridine derivatives for the preparation of functionalised enantioenriched δ ‐lactams using chiral copper catalysis. Experimental 13 C kinetic isotope effects and density functional theory calculations shed light on the reaction mechanism and the origin of enantioselectivity.

Chirality

10.1002/ange.202217328

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Efficient synthesis of 2H-chromene derivatives via a dual-organocatalytic reaction

Tetrahedron Letters (2020)

Siriphong Somprasong Watcharapon Prasitwatcharakorn Torsak Luanphaisarnnont

Pyrrolidine

Functional group

Reaction conditions

Simplicity

10.1016/j.tetlet.2020.152402

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Citations (7)

CCDC 2150559: Experimental Crystal Structure Determination

The Cambridge Structural Database (2023)

Siriphong Somprasong Marta Castiñeira Reis Syuzanna R. Harutyunyan

An entry from the Cambridge Structural Database, the world’s repository for small molecule crystal structures. The entry contains experimental data from a crystal diffraction study. The deposited dataset for this entry is freely available from the CCDC and typically includes 3D coordinates, cell parameters, space group, experimental conditions and quality measures.

10.5517/ccdc.csd.cc2b5tw7

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Enantioselective Nickel-Catalyzed Electrochemical Reductive Conjugate Alkenylation of α,β-Unsaturated Ketones

Chemical Science (2024)

Siriphong Somprasong Baonian Wan Syuzanna R. Harutyunyan

We present an asymmetric electrochemical nickel-catalysed reductive conjugate addition of alkenyl bromides/aryl iodides to α,β-unsaturated ketones in an undivided cell, which afforded β-alkenylate/arylate ketones in high yields with excellent enantioselectivities.

Conjugate

10.1039/d4sc06891b

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Catalytic Access to Chiral δ‐Lactams via Nucleophilic Dearomatization of Pyridine Derivatives

Angewandte Chemie International Edition (2022)

Siriphong Somprasong Marta Castiñeira Reis Syuzanna R. Harutyunyan

Nitrogen-bearing rings are common features in the molecular structures of modern drugs, with chiral δ-lactams being an important subclass due to their known pharmacological properties. Catalytic dearomatization of preactivated pyridinium ion derivatives emerged as a powerful method for the rapid construction of chiral N-heterocycles. However, direct catalytic dearomatization of simple pyridine derivatives are scarce and methodologies yielding chiral δ-lactams are yet to be developed. Herein, we describe an enantioselective C4-dearomatization of methoxypyridine derivatives for the preparation of functionalised enantioenriched δ-lactams using chiral copper catalysis. Experimental 13 C kinetic isotope effects and density functional theory calculations shed light on the reaction mechanism and the origin of enantioselectivity.

10.1002/anie.202217328

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Citations (18)

Grignard Reagent Addition to Pyridinium Salts: A Catalytic Approach to Chiral 1,4-Dihydropyridines

ACS Catalysis (2024)

Siriphong Somprasong Marta Castiñeira Reis Syuzanna R. Harutyunyan

Catalytic dearomatization of pyridinium salts is a powerful technique for constructing chiral N-heterocycles, which are crucial in alkaloid natural products and drugs. Despite its potential, progress in metal-catalyzed asymmetric dearomatization of pyridinium derivatives has been limited. Here, we present the enantioselective 1,4-dearomatization of pyridinium salts using Grignard reagents and chiral copper catalysis. This approach yields enantioenriched functionalized 1,4-dihydropyridines. Experimental kinetic isotope effects and density functional theory calculations provide insights into the reaction mechanism, regio- and enantioselectivity, and the rate-limiting step.

10.1021/acscatal.4c03520

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Citations (1)

Expanding the scope of catalytic asymmetric addition of Grignard reagents and validating the reaction mechanism

Siriphong Somprasong

The catalytic asymmetric addition of Grignard reagents to various organic electrophiles has a privileged position as a reliable methodology for synthetic chemists to exploit for the formation of carbon–carbon bonds and the creation of chirality in a single step. It constitutes a fundamental component of contemporary organic synthesis. These significant transformations have been extensively developed in recent decades and are widely employed in the synthesis of chiral natural products and bioactive molecules, including proteins and pharmaceuticals. The aim of this thesis is the design and development of novel sustainable catalytic processes based on stereoselective homogeneous catalysis complemented with mechanistic studies. We focus on asymmetric dearomatisation reactions involving Grignard reagents and pyridine derivatives, such as methoxypyridines and pyridinium salts, which are catalysed by chiral copper complexes. The combination of 13C kinetic isotope effects (KIEs) and density functional theory (DFT) calculations was used to investigate catalytic reaction mechanism.

Scope (computer science)

10.33612/diss.1082653871

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Direct Synthesis of Coumarin Derivatives from Alkynoic Esters via Dual Organocatalysis

Synlett (2022)

Torsak Luanphaisarnnont Peerawat Saejong Siriphong Somprasong Chaiwat Rujirasereesakul

Abstract An efficient synthetic method for coumarin derivatives was developed using a dual organocatalytic reaction. A combination of p-toluenesulfonic acid monohydrate and piperidine was found to efficiently catalyze the cyclization between salicylaldehydes and alkynoic esters to give various coumarin derivatives in good yield and high selectivity. Mechanistic and kinetic data suggested that the conjugate addition between piperidine and alkynoic esters played a crucial role in the reaction mechanism.

Piperidine

Conjugate

10.1055/a-1797-0386

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Citations (2)

Catalytic Asymmetric Addition and Substitution Reactions with Grignard Reagents: Do We Know It All?

European Journal of Organic Chemistry (2025)

Siriphong Somprasong Juana M. Pérez Marta Castiñeira Reis

Catalysis has been a cornerstone in organic synthesis, enabling a variety of highly efficient and selective C–C bond formation reactions, in particular enantioselective addition and substitution of Grignard reagents. Throughout time, we have gained significant understanding into how various factors, such as the influence of the metal source, the nature of the ligands, the substrates or temperature, affect these processes. Recent advances in computational chemistry have further enriched our understanding of this chemistry by elucidating the potential reaction mechanism and providing insight into the rate and enantio‐determining steps in these catalytic transformations. However, challenges persist, and aspects such as ligand optimisation, full mechanistic understanding and scalability remain underexplored. Computational methods, however, present a remarkable potential to surmount these enduring challenges.

Substitution (logic)

Grignard reagent

Substitution reaction

Grignard reaction

10.1002/ejoc.202401457

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