Copper-catalyzed multicomponent reaction of β-trifluoromethyl β-diazo esters enabling the synthesis of β-trifluoromethyl N,N-diacyl-β-amino esters

Beilstein Journal of Organic Chemistry, Год журнала: 2024, Номер 20, С. 212 - 219

Опубликована: Фев. 2, 2024

An efficient multicomponent reaction of newly designed β-trifluoromethyl β-diazo esters, acetonitrile, and carboxylic acids via an interrupted esterification process under copper-catalyzed conditions has been developed, which affords various unsymmetrical N , -diacyl-β-amino esters in good to excellent yields. The features mild conditions, a wide scope β-amino acids, also applicability large-scale synthesis, thus providing way for the synthesis β-diacylamino esters. Furthermore, this represents first example Mumm rearrangement

Язык: Английский

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Applications of chiral sulfinyl auxiliaries in the asymmetric synthesis of fluorinated amines and amino acids

Ukrainica Bioorganica Acta, Год журнала: 2023, Номер 18(1), С. 10 - 21

Опубликована: Июнь 30, 2023

This review article covers the developments made in collaboration by groups of Professors V. P. Kukhar and Bravo to synthetic applications sulfinyl compounds as versatile chiral auxiliaries for asymmetric preparation fluorinated amines amino acids. The potential field stereoselective transformations substrates is demonstrated diastereoselective methylene transfer from diazomethane carbonyl β-keto-γ-fluoroalkyl sulfoxides a general approach various oxirane derivatives, sulfoxide anions addition imines leading convenient α-fluoroalkyl α-amino acids, hydroxy amines, Mannich-type reaction between N-tert-butanesulfinyl-3,3,3-trifluoroacetaldimine protected alkyl glycolates furnishing β-trifluoromethyl isoserine derivatives additions phosphite or α-phosphonate using synthesis trifluoromethylated α- β-aminophosphonic Furthermore, Reformatsky reagent derived bromodifluoroethyl acetate well α,α-difluorophosphonate N-p-toluenesulfinyl allowing a,a-difluoro-b-amino acids α,α-difluoro-β-amino phosphonates enantiomerically pure form are described. Effect fluorine on mechanism stereochemical outcome these reactions briefly discussed

Язык: Английский

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Aza-Wittig reaction of (β-diazo-α,α-difluoroethyl)phosphonates with aldehydes for the synthesis of difluoromethylphosphonate-containing arylidene hydrazones

Journal of Fluorine Chemistry, Год журнала: 2023, Номер 273, С. 110226 - 110226

Опубликована: Ноя. 29, 2023

Язык: Английский

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Cu‐Catalyzed Reaction of Trifluoromethylated β‐Keto Diazos and Nitriles Proceeding via H₂O Addition to Nitrile Ylides

Advanced Synthesis & Catalysis, Год журнала: 2024, Номер 366(16), С. 3443 - 3449

Опубликована: Май 22, 2024

Abstract A Cu‐catalyzed multi‐component reaction of trifluoromethylated β‐amino ketones and nitriles using tert ‐butyl nitrite as a diazotization reagent has been developed. Under the optimized conditions, N ‐trifluoroalkyl amides were obtained with yields up to 87%. Control experiments computational studies reveal that proceeds through generation diazo, in situ formation nitrile ylide, water addition final enol tautomerism. This approach features mild wide substrate tolerance, scale‐up applicability, which provides an efficient practical strategy for amide synthesis.

Язык: Английский

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Recent Advances in Diazophosphonate Chemistry: Reactions and Transformations

Synthesis, Год журнала: 2024, Номер unknown

Опубликована: Сен. 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

Язык: Английский

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Recent Advances on the Synthesis and Application of α,α-Difluoro-β-aminophosphonates

Chinese Journal of Organic Chemistry, Год журнала: 2024, Номер 44(12), С. 3686 - 3686

Опубликована: Янв. 1, 2024

Язык: Английский

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Regioselective synthesis of 3H-Pyrazoles bearing difluoromethyl phosphonate group

Journal of Fluorine Chemistry, Год журнала: 2023, Номер 273, С. 110218 - 110218

Опубликована: Ноя. 21, 2023

Язык: Английский

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Iron-catalyzed sulfur alkylation of sulfenamides with in situ-generated 2,2,2-trifluorodiazoethane

Journal of Fluorine Chemistry, Год журнала: 2023, Номер 273, С. 110219 - 110219

Опубликована: Ноя. 24, 2023

Язык: Английский

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Synthesis of α-Fluoro-β-Ketophosphonates through Rh-Catalyzed Hydration/C–F Bond Cleavage

Synfacts, Год журнала: 2023, Номер 19(10), С. 1010 - 1010

Опубликована: Сен. 14, 2023

Key words rhodium catalysis - carbenes C–F bond cleavage difluoro diazoalkanes

Язык: Английский

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