Asymmetric 1,3-Dipolar Cycloadditions for the Construction of Enantiomerically Pure Heterocycles. A Review

Karlsson, Staffan; Högberg, Hans‐Erik

doi:10.1080/00304940109356583

Cited by 176 publications

(34 citation statements)

References 201 publications

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“…One recrystallization from EtOAc/heptane furnished 3b (11.2 g, 50.2 mmol; 56%) as colorless crystals in Ͼ 99% chemical purity and in Ͼ 99:1 dr and Ͼ 99% ee. [ (3S,3aR,6aR)-3-(Cyclopent-1-en-1-yl) 2 /C (100 mg) and HCl (37% aq. ; 0.3 mL) in MeOH (10 mL) were stirred under hydrogen at ambient pressure and room temperature overnight.…”

Section: General Methods For the 13-dipolar Cycloaddition Reactionsmentioning

confidence: 99%

Organocatalysts Promote Enantioselective 1,3‐Dipolar Cycloadditions of Nitrones with 1‐Cycloalkene‐1‐carboxaldehydes

2003

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In the presence of enantiopure organocatalysts, 1‐cycloalkene‐1‐carboxaldehydes and various nitrones furnished fused isoxazolidines. Thus, some chiral pyrrolidinium salts catalyzed the formation of such cycloadducts in high diastereo‐ and enantioselectivity (up to 92% ee). The predominant diastereomer, the exo one, was mostly obtained in excellent diastereoselectivity (> 99:1 dr). Furthermore, after recrystallization of one of the cycloadducts, this was obtained enantiomerically pure (> 99% ee). The absolute configuration of one of the cycloadducts was determined. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003)

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Section: General Methods For the 13-dipolar Cycloaddition Reactionsmentioning

confidence: 99%

Organocatalysts Promote Enantioselective 1,3‐Dipolar Cycloadditions of Nitrones with 1‐Cycloalkene‐1‐carboxaldehydes

2003

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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%

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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“…Hence the synthesis of substituted spiro-oxindole and oxazolidines carries special importance in synthetic organic chemistry. Of the different strategies to synthesise the oxazolidine ring-system, 1,3-dipolar cycloaddition is a leading technique [26][27][28][29][30]. In the present work, an interesting route utilising 1,3-dipolar cycloaddition has been used to synthesise oxazolidines [31][32][33][34].…”

Section: Introductionmentioning

confidence: 99%

Simple and efficient routes to substituted oxazolidine and spiro-oxindole systems by one-pot synthetic strategies

Gayen

Banerji

2014

Monatsh Chem

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Simple and efficient strategies towards the synthesis of substituted spiro-oxindole and oxazolidine systems by one-pot multi-component catalyst-free reactions utilising aryl aldehydes and a-amino acids have been developed. Owing to their complicated structure and ring strain spiro-oxindole moieties are not easily synthesised. In either route 1,3-dipolar cycloadditions involving non-stabilised azomethine ylides as intermediates, generated in situ from amino acids and aldehydes, with the dipolarophile present in the reaction mixture viz. (E)-bnitrostyrene, were utilised. The route to substituted oxazolidines involved cycloaddition to the C=O bond of a second molecule of the aldehyde.

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Asymmetric 1,3-Dipolar Cycloadditions for the Construction of Enantiomerically Pure Heterocycles. A Review

Cited by 176 publications

References 201 publications

Organocatalysts Promote Enantioselective 1,3‐Dipolar Cycloadditions of Nitrones with 1‐Cycloalkene‐1‐carboxaldehydes

Organocatalysts Promote Enantioselective 1,3‐Dipolar Cycloadditions of Nitrones with 1‐Cycloalkene‐1‐carboxaldehydes

Asymmetric 1,3-dipolar cycloadditions of acrylamides

Simple and efficient routes to substituted oxazolidine and spiro-oxindole systems by one-pot synthetic strategies

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