Advances in the Synthesis of Methylated Products Through Direct Approaches: A Guide for Selecting Methylation Reagents

Chen, Yantao

doi:10.1002/9783527831883.ch34

The Chemical Transformations of C1 Compounds 2022

DOI: 10.1002/9783527831883.ch34

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Advances in the Synthesis of Methylated Products Through Direct Approaches: A Guide for Selecting Methylation Reagents

Yantao Chen¹

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2024

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Cited by 2 publications

References 376 publications

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Strategies for Using Quaternary Ammonium Salts as Alternative Reagents in Alkylations

Templ,

Schnürch

2024

Chemistry A European J

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Alkylation reactions are pivotal in organic chemistry, with wide‐ranging utilization across various fields of applied synthetic chemistry. However, conventional reagents employed in alkylations often pose substantial health and exposure risks. Quaternary ammonium salts (QAS) present a promising alternative for these transformations offering significantly reduced hazards as they are non‐cancerogenic, non‐mutagenic, non‐flammable, and non‐corrosive. Despite their potential, their use in direct organic transformations remains relatively unexplored. This review outlines strategies for utilizing QAS as alternative reagents in alkylation reactions, providing researchers with safer approaches to chemical synthesis.

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Strategies for Using Quaternary Ammonium Salts as Alternative Reagents in Alkylations

Templ,

Schnürch

2024

Chemistry A European J

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Asymmetric Total Synthesis of All Rugulovasine Stereoisomers and Preliminary Evaluation of Their Biological Properties

et al. 2022

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A unified enantioselective synthesis and the biological evaluation of all rugulovasine stereoisomers are reported. The syntheses are centered on the divergent and stereochemical modular combination of each enantiomer of 4‐amino Uhle's ketone and a methacrylate derivative to build the unsaturated oxaspirolactone moiety by the Dreiding‐Schmidt reaction, followed by Fukuyama alkylation to afford the required N‐methyl secondary amine in excellent yield. The modularity of this divergent approach, the diastereoselectivities of the reactions, and the late‐stage site‐selective methylation permit the rapid asymmetric syntheses of all rugulovasine stereoisomers, including the first total syntheses of optically pure (+)‐ and (−)‐rugulovasine B and their trideuteromethylated derivatives. All enantiopure stereoisomers of rugulovasine were tested for their binding affinities to dopamine, serotonin, and adrenergic neuroreceptors, revealing their preferred selectivity for the serotonin 1 A receptor.

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Advances in the Synthesis of Methylated Products Through Direct Approaches: A Guide for Selecting Methylation Reagents

Cited by 2 publications

References 376 publications

Strategies for Using Quaternary Ammonium Salts as Alternative Reagents in Alkylations

Strategies for Using Quaternary Ammonium Salts as Alternative Reagents in Alkylations

Asymmetric Total Synthesis of All Rugulovasine Stereoisomers and Preliminary Evaluation of Their Biological Properties

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