Asymmetric phase-transfer catalysis

Nature Reviews Chemistry, Journal Year: 2024, Volume and Issue: 8(11), P. 851 - 869

Published: Oct. 9, 2024

Language: Английский

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Recent Progress in Chiral Quaternary Ammonium Salt-Promoted Asymmetric Nucleophilic Additions

ACS Catalysis, Journal Year: 2025, Volume and Issue: 15(3), P. 1973 - 2001

Published: Jan. 20, 2025

Chiral quaternary ammonium ion-pair organocatalysis has been widely used in the facile synthesis of chiral molecules with challenging stereocenters. Especially, numerous asymmetric nucleophilic addition reactions have facilitated this strategy. This review systematically summarizes additions promoted by salts past decade. The content is organized according to types electrophiles involved these catalytic transformations. Our own perspectives on future development within highly active research field are also provided.

Language: Английский

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Highly Enantioselective Synthesis of [1,2,4]Triazino[5,4-a]isoquinoline Derivatives via (3 + 3) Cycloaddition Reactions of Diazo Compounds and Isoquinolinium Methylides

Organic Letters, Journal Year: 2022, Volume and Issue: 24(21), P. 3766 - 3771

Published: May 23, 2022

An array of chiral [1,2,4]triazino[5,4-a]isoquinoline derivatives were obtained in excellent yields (up to 98%) and with enantioselectivities 99% ee) via a new highly asymmetric (3 + 3) cycloaddition reaction diazo compounds isoquinolinium methylides, bifunctional phase-transfer catalyst (PTC). Density functional theory calculations show that PTC has bridge role the deprotonation/protonation process. The products transformed into densely functionalized polycyclic heterocompounds multiple stereocenters.

Language: Английский

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Reactivity of quinone methides with carbenes generated from α-diazocarbonyl compounds and related compounds

Chemical Communications, Journal Year: 2022, Volume and Issue: 59(1), P. 29 - 42

Published: Dec. 8, 2022

Over the years, quinone methides have broadly been applied in synthesis and biological systems for synthesizing heterocyclic compounds biologically active molecules. In this feature article, we discussed novel uncovered reactivity of o-quinone methides, p-quinone aza-o-quinone indolyl-2-methides with carbenes generated from α-diazocarbonyl related compounds. Two situ-generated transient intermediates undergo cycloannulation reactions, metathesis-type 1,6-conjugate addition cyclopropanation many other transformations to access nitrogen- oxygen-containing beyond. The is observed various metal catalysts, Brønsted-acids, Lewis acids, phase transfer additives, visible-light-induced transformations.

Language: Английский

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Chiral-boron-Lewis-acid-catalysed desymmetric ring expansion of 4-substituted cyclohexanones with α-diazomethylphosphonates

Organic Chemistry Frontiers, Journal Year: 2023, Volume and Issue: 10(6), P. 1564 - 1569

Published: Jan. 1, 2023

A methodology to access chiral cyclic β-ketophosphonates with a stereogenic center at the α-position has been established via an asymmetric desymmetrizing ring-expansion reaction of 4-substituted cyclohexanones α-diazophosphonates catalysed by boron Lewis acid.

Language: Английский

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Quinquevalent phosphorus acids

Royal Society of Chemistry eBooks, Journal Year: 2024, Volume and Issue: unknown, P. 109 - 231

Published: Feb. 21, 2024

This chapter shows, as in previous years, the most important achievements of 2021 year area organo-phosphorus compounds containing: three P–O bonds (Section 2: phosphoric acids and their derivatives), two one P–C 3: phosphonic derivatives) well 4: phosphinic addition to phosphoryl group P═O, present all groups compounds. Each main sections covers “synthesis reactions” including pure synthesis without applications, biological applications” miscellaneous directed towards non-biological applications. At end each subsection, corresponding are shown for hetero-analogues which phosphorus–oxygen have been replaced by phosphorus–heteroatom P–X and/or P═Y (X, Y = N, S or Se). The subsection on quinquevalent phosphorus derivatives catalysts has placed, usual, at entire chapter, after a review As devoted dominated over smaller section derivatives, literature references these remained ratio 4 : 12 1. A dynamic, five-fold increase number works, subject chiral catalysts, recorded this year.

Language: Английский

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Recent Advances in Diazophosphonate Chemistry: Reactions and Transformations

Synthesis, Journal Year: 2024, Volume and Issue: unknown

Published: Sept. 5, 2024

Abstract Diazophosphonates function as indispensable synthetic intermediates within the domain of organic chemistry, serving precursors for a diverse range molecules, with potential applications bioactive compounds. α-Diazomethylphosphonates showcase expansive reactivity and elevated levels enantioselectivity in asymmetric transformations, especially conjunction suitable catalyst systems. This review compiles latest advancements diazophosphonate chemistry from 2016 to 2024, highlighting their transformative synthesis. Diazophosphonates, regarded revolutionary compounds, exhibit unique attributes carbene precursors, driving chemical reactions such [3+2] cycloaddition, [3+3] substitution reactions. Their adaptability functional group conversions underscores pivotal role various methodologies. The highlights growing interest among chemists, fostering novel strategies expanding application horizons. multifaceted utility diazophosphonates reagents, intermediates, catalysts significance modern pharmaceutical applications, prompting further exploration into this dynamic field. 1 Introduction 2 Cycloaddition Reactions 3 Asymmetric 4 5 Substitution 6 Carbene Precursors 7 Chemistry Fluorinated Compounds 8 Other 9 Future Directions 10 Conclusion

Language: Английский

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