The highly enantioselective 1,3-dipolar cycloaddition of alkyl glyoxylate-derived nitrones to E-crotonaldehyde catalyzed by hybrid diamines

Weseliński, Łukasz J.; Słyk, Edyta; Jurczak, Janusz

doi:10.1016/j.tetlet.2010.11.015

Cited by 30 publications

(10 citation statements)

References 29 publications

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“…As a representative example of the current state of the art, isoxazolidines produced by catalytic asymmetric 1,3-DC reactions of acyclic aldonitrones with different kinds of dipolarophiles are highlighted in Figure : compounds 5 – 8 from electron-rich dipolarophiles (vinyl ethers), − compounds 9 and 10 from neutral ones (allylic alcohols), , and compounds 11 – 25 from electron-poor ones (enals, enamides, enones, nitro olefins, methylene malonates). ,− Only a limited number of examples concern nitrones bearing protecting groups at the nitrogen atom, mainly using a benzyl group. In other cases, N -substituents are an aryl or a methyl group.…”

Section: Synthetic Strategies To Prepare the Isoxazolidine Ringmentioning

confidence: 99%

Isoxazolidine: A Privileged Scaffold for Organic and Medicinal Chemistry

et al. 2016

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The isoxazolidine ring represents one of the privileged structures in medicinal chemistry, and there have been an increasing number of studies on isoxazolidine and isoxazolidine-containing compounds. Optimization of the 1,3-dipolar cycloaddition (1,3-DC), original methods including electrophilic or palladium-mediated cyclization of unsaturated hydroxylamine, has been developed to obtain isoxazolidines. Novel reactions involving the isoxazolidine ring have been highlighted to accomplish total synthesis or to obtain bioactive compounds, one of the most significant examples being probably the thermic ring contraction applied to the total synthesis of (±)-Gelsemoxonine. The unique isoxazolidine scaffold also exhibits an impressive potential as a mimic of nucleosides, carbohydrates, PNA, amino acids, and steroid analogs. This review aims to be a comprehensive and general summary of the different isoxazolidine syntheses, their use as starting building blocks for the preparation of natural compounds, and their main biological activities.

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Section: Synthetic Strategies To Prepare the Isoxazolidine Ringmentioning

confidence: 99%

Isoxazolidine: A Privileged Scaffold for Organic and Medicinal Chemistry

et al. 2016

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“…Additionally Jurczak et al. have developed a method for the construction of chiral isooxazolidines by application of crotonaldehyde and glyoxalate derived nitrones 199…”

Section: Cycloadditionsmentioning

confidence: 99%

“…[197] Another example for the construction of chiral pyrazolidines was reported by Shiro et al [198] Additionally Jurczak et al have developed a method for the construction of chiral isooxazolidines by application of crotonaldehyde and glyoxalate derived nitrones. [199] For the construction of cyclopentenes allenes are very valuable starting compounds. Lu et al described a new strategy for the construction of these structures bearing a quaternary all carbon center.…”

Section: Wwwchemeurjorgmentioning

confidence: 99%

“…The self-condensation of alkynals was achieved by diarylprolinol catalysis (199) and linked with a domino organocatalytic oxa-Diels-Alder reaction to yield a variety of polysubstituted chiral 3,4-dihydropyrans. It is assumed, that the alkynal self-condensation proceeds through a secondary amine-catalyzed, triple bond hydration and subsequent aldol condensation (Scheme 105).…”

Section: Multicomponent and Cascade Reactionsmentioning

confidence: 99%

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Recent Advances in Organocatalytic Methods for Asymmetric CC Bond Formation

Scheffler

Mahrwald

2013

Chemistry A European J

197

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Beyond a doubt organocatalysis belongs to the most exciting and innovative chapters of organic chemistry today. Organocatalysis has emerged not only as a complement to metal-catalyzed reactions and to biocatalysis over the last decade, but also provides new asymmetric organocatalyzed reactions that cannot be accomplished by metal- or biocatalyzed reactions so far. A large number of organocatalytic processes are already well established in organic synthesis. Nevertheless, the number of publications in this field is still on the increase; new important results are produced constantly. This review gives a detailed overview of the latest developments and main streams in organocatalyzed asymmetric CC bond formation processes of the last three years. It is intended to outline the most important current findings focused on especially new synthetic methodologies.

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“…28,29 In light of these facts, many N-heterocyclic carbene ligands are designed with different structural motifs, coordinated with various transition metals like copper(I), silver(I), gold(I), mercury(II), palladium(II), rhodium(III), ruthenium(II), etc., and are employed not only for various organometallics 30,31 but for organocatalytic 1492 Sonali Ramgopal Mahule transformations. 32 Herein, we report and discuss one such versatile chiral structural motif, BINOL and its benzimidazole based N-heterocyclic carbene complexes. R and S enantiomers of BINOL have been extensively used as chiral ligands in a number of asymmetric reactions.…”

Section: Introductionmentioning

confidence: 99%

Axially chiral benzimidazolium based silver(I) and gold(I) bis-NHC complexes of R-BINOL scaffold: synthesis, characterization and DFT studies

Mahule

2017

J Chem Sci

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The axially chiral ligand of R-BINOL scaffold was synthesized by a series of manipulations which involved different chemical reactions to obtain the desired sliver(I) and gold(I) {[L(L-NHC) 2 ]M}Cl (L = 3,3-dimethyl-2,2-dimethoxy-1,1-binaphthyl, L = i-propyl-benzo[d]imidazole) (M =Ag and Au) complexes. Enantiopure R-BINOL was employed as a basic unit to synthesize a benzimidazole based bis-NHC ligand 1g which was obtained through the formation of different intermediate 1(a-f) compounds. The newly synthesized bis-NHC ligand precursor (1g) and its corresponding {[L(L-NHC) 2 ]Ag}Cl (1h) and {[L(L-NHC) 2 ]Au}Cl (1i) complexes were characterized by different spectroscopic techniques. The geometries of the optimized structure of the complexes 1h and 1i were computed at the B3LYP/SDD, 6-31G(d) level. Low temperature fluorescence spectroscopic studies did not show any evidence for the weak metal-metal interaction in these complexes.

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The highly enantioselective 1,3-dipolar cycloaddition of alkyl glyoxylate-derived nitrones to E-crotonaldehyde catalyzed by hybrid diamines

Cited by 30 publications

References 29 publications

Isoxazolidine: A Privileged Scaffold for Organic and Medicinal Chemistry

Isoxazolidine: A Privileged Scaffold for Organic and Medicinal Chemistry

Recent Advances in Organocatalytic Methods for Asymmetric CC Bond Formation

Axially chiral benzimidazolium based silver(I) and gold(I) bis-NHC complexes of R-BINOL scaffold: synthesis, characterization and DFT studies

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