Asymmetric 1,3-Dipolar Cycloaddition Reactions

Gothelf, Kurt V.; Jørgensen, Karl Anker

doi:10.1021/cr970324e

Cited by 1,870 publications

(683 citation statements)

References 389 publications

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“…The [3＋2] cycloaddition reaction of azomethine ylide with olefinic dipolarophiles constitutes a straightforward approach to the synthesis of highly substituted chiral pyrrolidine derivatives. [34][35][36][37][38][39][40][41][42][43][44][45][46][47][48][49][50] So far, many laboratories have reported the catalytic asymmetric [3＋2] cycloadditions with azomethine ylides by means of a variety of ligand-metal combinations. Our group reported that the ferrocenyloxazoline derived chiral N,P ligand showed excellent performance in the Ag(I)-catalyzed enantioselective 1,3-dipolar cycloaddition of azomethine ylides.…”

Section: Resultsmentioning

confidence: 99%

Synthesis of MeO-PEG-Supported Ferrocenyloxazoline Ligands and Their Application in Asymmetric Catalysis

Liu¹,

Shi²,

Wang³

et al. 2013

Acta Chim. Sinica

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A simple synthesis of ferrocenyloxazoline derived chiral N,P ligands and N,S ligands immobilized on a MeO-PEG-support is described. The metal complexes of chiral ligands have been successfully applied to 1,3-dipolar cycloaddition reaction of azomethine ylides and asymmetric allylic substitution reaction, providing the products with up to 97% ee and 90% ee, respectively. The MeO-PEG-supported metal complex catalysts can be recycled easily and reused.

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Section: Resultsmentioning

confidence: 99%

Synthesis of MeO-PEG-Supported Ferrocenyloxazoline Ligands and Their Application in Asymmetric Catalysis

Liu¹,

Shi²,

Wang³

et al. 2013

Acta Chim. Sinica

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“…6,10,[14][15][16]19 Control of the diastereo-and enantioselectivity in the addition step is the major challenge in asymmetric 1,3-dipolar cycloadditions. It is possible to control the diastereoselectivity by choosing the appropriate substrates or using a metal complex acting as a catalyst, and the enantioselectivity can be controlled by either choosing a chiral 1,3-dipole, a chiral dipolarophile or a chiral catalyst.…”

Section: Asymmetric 13-dipolar Cycloadditionsmentioning

confidence: 99%

“…In Jorgensen's review on asymmetric 1,3-dipolar cycloadditions in 1998, 10 he described his unpublished findings on the affect of the TiTADDOLate catalyst 96 in the cycloaddition of ethyl diazoacetate 97 to the oxazolidinone 76, with enantiomeric excesses of 30-40% achieved (Scheme 60).…”

Section: Scheme 59mentioning

confidence: 99%

Asymmetric 1,3-dipolar cycloadditions of acrylamides

2010

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This critical review, which is relevant to researchers in synthetic organic chemistry, focuses on asymmetric 1,3-dipolar cycloadditions with acrylamides. The use of chiral acrylamides as dipolarophiles leads to high levels of stereocontrol, due to conformational constraint in the acrylamides. Employment of chiral tertiary acrylamides containing nitrogen heterocycles is particularly effective in controlling the stereoselectivity. Following a general overview of 1,3-dipolar cycloadditions, the main body of the review focuses on asymmetric 1,3-dipolar cycloadditions of acrylamides with nitrile oxides, nitrones, diazoalkanes and azomethine ylides, with particular emphasis on the rationale for the observed stereocontrol (215 references)

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“…The heterocyclic's forms the basic skeleton for a wide variety of chemical compounds interest, biological, pharmacological and industrial [1], [2]. Note that two-thirds of the organic compounds known from the literature are heterocyclic [3], such as sugars which are organic molecules very widespread in the major cell types described: bacteria, and in the connective tissues and cell membranes of animals, vegetable cell.…”

Section: Introductionmentioning

confidence: 99%

A Novel Method for the Deprotection of N-Boc-D-Glucosamine-Ac by Irradiation via Microwave

Bouleghlem¹,

Aouf²,

Zidane³

2016

IJCEA

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Abstract-Since the microwave was used for the first time in 1986 in the field of the organic synthesis, the reactions assisted by microwaves are used more and more in the strategies of synthesis. It meets an interest growing because of its great effectiveness and its extreme profitability due to reduced reaction times, better outputs and obtaining purer products. Its particular use, was the subject of a method around whose developed a green chemistry. Several developed, he was devoted, and the last in date is a work C.O. Kappe in 2005. Within the framework of this work, we will try to develop an aspect of the chemistry of the protective groupings: chimioselective protection deprotection of N-Boc-Glucosamine-Acyle by irradiation under domestic microwave. The usual spectroscopic methods ( 1 H NMR, IR and MS) were made profitable for elucidation synthesized structures.

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Asymmetric 1,3-Dipolar Cycloaddition Reactions

Cited by 1,870 publications

References 389 publications

Synthesis of MeO-PEG-Supported Ferrocenyloxazoline Ligands and Their Application in Asymmetric Catalysis

Synthesis of MeO-PEG-Supported Ferrocenyloxazoline Ligands and Their Application in Asymmetric Catalysis

Asymmetric 1,3-dipolar cycloadditions of acrylamides

A Novel Method for the Deprotection of N-Boc-D-Glucosamine-Ac by Irradiation via Microwave

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