Kinugasa reaction: an ‘ugly duckling’ of β-lactam chemistry

Stecko, Sebastian; Furman, Bartłomiej; Chmielewski, Marek

doi:10.1016/j.tet.2014.06.024

Cited by 75 publications

(29 citation statements)

References 155 publications

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“…In addition to isoxazoline synthesis, nitrones are key precursors to diverse β-lactam structures through the copper(I)-catalyzed Kinugasa reaction with acetylides [ 7 , 8 ]. Since the initial report of the reaction between copper(I) acetylides and nitrones in pyridine in 1972 [ 8 ], the scope and limitations of the Kinugasa reaction have been explored by a number of research groups [ 9 , 10 , 11 ]. Recent progress in expanding the scope of the reaction has afforded the transition from requiring polar aprotic reaction media to an ‘on water’ approach, as well as employing detergents to allow for a micelle-promoted reaction to occur in aqueous medium [ 12 ].…”

Section: Introductionmentioning

confidence: 99%

Kinugasa Reactions in Water: From Green Chemistry to Bioorthogonal Labelling

et al. 2015

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Abstract:The Kinugasa reaction has become an efficient method for the direct synthesis of β-lactams from substituted nitrones and copper(I) acetylides. In recent years, the reaction scope has been expanded to include the use of water as the solvent, and with micelle-promoted [3+2] cycloadditions followed by rearrangement furnishing high yields of β-lactams. The high yields of stable products under aqueous conditions render the modified Kinugasa reaction amenable to metabolic labelling and bioorthogonal applications. Herein, the development of methods for use of the Kinugasa reaction in aqueous media is reviewed, with emphasis on its potential use as a bioorthogonal coupling strategy.

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Section: Introductionmentioning

confidence: 99%

Kinugasa Reactions in Water: From Green Chemistry to Bioorthogonal Labelling

et al. 2015

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“…This class of amides, activated by an iridium complex, undergoes hydrosilylation of the carbonyl group and desilylation/elimination of the hydroxyl group to form a nitrone. The developed methodology was applied to the formation of macrocyclic nitrones ( Figure 2K ), key intermediates for the synthesis of biologically active natural products such as manzamine alkaloids (Brandi et al, 2017 ) and the β-lactam core (Stecko et al, 2014 ). Moreover, in this case, an N -silyloxyamide was used as a substrate, and a 15-membered cyclic nitrone was captured by cycloaddition with methyl acrylate to form an enantiomeric isoxazolidine.…”

Section: Natural Products Synthesismentioning

confidence: 99%

Reductive Functionalization of Amides in Synthesis and for Modification of Bioactive Compounds

Czerwiński

Furman

2021

Front. Chem.

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In this review, applications of the amide reductive functionalization methodology for the synthesis and modification of bioactive compounds are covered. A brief summary of the different protocols is presented in the introduction, followed by the synthetic application of these in late-stage functionalization, leading to known pharmaceuticals or to their derivatives, including bioisosteres, with potential higher activity as the main axis of the article. The synthetic approach to natural products based on amide reduction is also discussed; however, this is given in a condensed form focusing on recent or as yet unexplored applications due to a number of recently published excellent reviews covering this topic. The aim of this review is to illustrate the potential of reductive functionalization of amides as an elegant and useful tool in the synthesis of bioactive compounds and inspire further work in this field.

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“…36 The same transformation was reported shortly after by Irwin and Ding, highlighting the preferential generation of the cis βlactam over the trans analogue, 37 and has been revisited in several occasions during the past decades. [38][39][40] Scheme 9 Original acetylide reaction described by Kinugasa in the 1970s β-Lactams have generated significant interest in the chemistry community, primarily because of their use as antibiotics. This family of compounds contains penicillins, cephalosporins, monobactams, and carbapenems.…”

Section: The Kinugasa Reaction With Copper Acetylidesmentioning

confidence: 99%