Highly Diastereo‐ and Enantioselective Silver‐Catalyzed Double [3+2] Cyclization of α‐Imino Esters with Isocyanoacetate

Shao, Pan‐Lin; Liao, Jia‐Yu; Ho, Yee Ann; Zhao, Yu

doi:10.1002/ange.201402788

Cited by 29 publications

(8 citation statements)

References 63 publications

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“…Asymmetric silver‐catalyzed pseudo‐three‐component domino Mannich‐type/cyclization reactions of α‐imino esters 328 and two equivalents of isocyanoacetates 329 were recently developed by Zhao et al 146. This process was catalyzed by a combination of a quinine‐derived phosphine 330 with Ag 2 O in THF at −20 °C and afforded chiral highly functionalized linked oxazole‐imidazolines 331 as almost single diastereomers bearing an anti ‐diamine moiety (>90% de ) in good yields of up to 99% and enantioselectivities of up to 99% ee (Scheme ).…”

Section: Enantioselective Metal‐catalyzed Multi‐component Reactionsmentioning

confidence: 99%

Recent Developments in Enantioselective Metal‐Catalyzed Domino Reactions

Pellissier

2016

Adv Synth Catal

109

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International audienceThis review updates the major progress in the field of enantioselective one-, two-, and multicomponent domino reactions promoted by chiral metal catalysts, covering the literature since the beginning of 2012. It illustrates how enantioselective metal-catalyzed processes have emerged as outstanding tools for the development of a wide variety of fascinating one-pot asymmetric domino reactions, allowing complex and diverse structures to be easily generated from simple materials in a single step. During the last 4 years, a myriad of already existing as well as completely novel and powerful asymmetric domino processes have been developed on the basis of asymmetric metal catalysis, taking economical advantages, such as avoiding costly protecting groups and time-consuming purification procedures after each step

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Section: Enantioselective Metal‐catalyzed Multi‐component Reactionsmentioning

confidence: 99%

Recent Developments in Enantioselective Metal‐Catalyzed Domino Reactions

Pellissier

2016

Adv Synth Catal

109

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“…Katritzky and co-workers have replaced TosMIC by benzotriazolyl methyl isocyanide in original van Leusen method. 16 Alternative approaches are reaction of active methylene isocyanides with phenyl carboxylates, 17 multicomponent reaction of amines, aldehydes, ketones and α-acidic isocyanides, 18 Schöllkopf condensation of lithiated methyl isocyanides with carboxylic acid chlorides, 19 oxidative decarboxylation-cyclization of αoxo carboxylates and isocyanides, 20 cycloaddition of isocyanides with methyl ketones, 21 cycloaddition of active methylene isocyanides with acid chlorides in flow reactor. 22 Cuprous iodide catalysed cyclization of isocyanide enones, 23 Ugi/Robinson-Gabriel synthesis 24 and conversion of carboxylic acid to acid chlorides followed by reaction with ethyl isocyanoacetate.…”

Section: Introductionmentioning

confidence: 99%

A sequential one-pot tandem approach for the synthesis of 4-tosyl-5-aryloxazoles from carboxylic acids

et al. 2018

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An efficient method for the synthesis of 4-tosyl-5-aryloxazoles directly from aromatic carboxylic acids has been reported. The method involves the conversion of aromatic carboxylic acids to tosyl carboxylates by treating with tosyl chloride in the presence of potassium carbonate and its subsequent reaction with tosylmethyl isocyanide in the presence of sodium hydride to get 4-tosyl-5-aryloxazoles.

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“…Isocyanides, as versatile building blocks with diverse reactivities, have been extensively investigated in the transitionmetal-catalyzed transformations to construct numerous valuable nitrogen-containing compounds. [11] Among the studied transition-metal-catalysts investigated, silver catalyst exhibits a remarkable capacity for the activation of isocyanides, allowing their reactions with many different types of electrophilic reagents, such as carbonyls, [12] imines, [13] alkenes, [14] α-imino esters, [15] allenoates, [16] fulvenes, [17] and alkynes [18] for constructing diverse heterocyclic compounds. [19] Additionally, silver salts have been also utilized in the radical chemistry of 2isocyanobiphenyls for the construction of 6-substituted phenanthridines.…”

mentioning

confidence: 99%

Silver‐Catalyzed Acyl Nitrene Transfer Reactions Involving Dioxazolones: Direct Assembly of N‐Acylureas

Yang

Xu²,

Chen

et al. 2020

Eur J Org Chem

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Dioxazolones and isocyanides are useful synthetic building blocks, and have attracted significant attention from researchers. However, the silver-catalyzed nitrene transfer reaction of dioxazolones has not been investigated to date. Herein, a silvercatalyzed acyl nitrene transfer reaction involving dioxazolones, isocyanides, and water was realized in the presence of Ag 2 O to afford a series of N-acylureas in moderate to good yields. The incorporation of an amide moiety into a molecule is of considerable importance because of the presence of this substructure in many biologically active molecules and natural products. [1] In the late 1960s, 1,4,2-dioxazol-5-ones (dioxazolones) 1 were identified by Sauer and Mayer as safe alternatives to acyl azides for N-acyl nitrene formation. [2] Owing to their low cost, ready availability, and environmental friendliness, 1,4,2dioxazol-5-ones have been extensively studied as amidating reagents in the past several years. In 2009, Dubé et al. published a pioneering method to prepare isocyanates by employing 1,4,2-dioxazol-5-ones. [3] Later, Bolm and co-workers reported the first light-induced ruthenium-catalyzed N-acyl nitrene transfer to sulfides and sulfoxides by the decarboxylation of 1,4,2dioxazol-5-ones (eq 1, Scheme 1). [4] Subsequently, dioxazolones were reported as amidating reagents for Rh-catalyzed CÀ H amidation by the Chang group. [5] Thereafter, a series of Rh-, [6] Co-, [7] and Ir-catalyzed [8] CÀ H amidation reactions were developed using this amidating reagent (eq 2, Scheme 1). Furthermore, Li, Zhu, Glorius, Ackermann, and other research groups described the cascade C À H amidation and cyclization reactions for the syntheses of various heterocycles. [9] Bruin and co-workers recently reported the fast N-acyl amidations via Cucatalyzed three-component reaction of aryl acetylenes, amines, and 1,4,2-dioxazol-5-ones (eq 3, Scheme 1). [10] However, to the best of our knowledge, the silver-catalyzed reaction of 1,4,2dioxazol-5-one via acyl nitrene has not been reported in the literature.

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Highly Diastereo‐ and Enantioselective Silver‐Catalyzed Double [3+2] Cyclization of α‐Imino Esters with Isocyanoacetate

Cited by 29 publications

References 63 publications

Recent Developments in Enantioselective Metal‐Catalyzed Domino Reactions

Recent Developments in Enantioselective Metal‐Catalyzed Domino Reactions

A sequential one-pot tandem approach for the synthesis of 4-tosyl-5-aryloxazoles from carboxylic acids

Silver‐Catalyzed Acyl Nitrene Transfer Reactions Involving Dioxazolones: Direct Assembly of N‐Acylureas

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