Chiral catalysts in the stereoselective synthesis of pyrrolidine derivatives via metallo-azomethine ylides

Husinec, Suren; Savić, Vladimir

doi:10.1016/j.tetasy.2005.05.020

Cited by 188 publications

(33 citation statements)

References 75 publications

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“…Azomethine ylides are mostly generated in situ due to their high reactivity and/or transient existence; however, in some cases, stabilized ylides have been isolated [19][20][21]. The most frequent type of 1,3-dipolar cycloaddition reaction of azomethine ylides is that with alkenyl or alkynyl dipolarophiles substituted with electron-withdrawing groups, providing access to pyrrolidine-containing molecules of biological [18,[22][23][24][25][26] or materials science interest [27][28][29][30][31]. The reactions with multiple bonded heteroatom systems such as carbonyl, thiocarbonyl, isothiocyanato, imino, isocyanato, nitrile, nitroso, and azo derivatives are also known, but less well studied [7,16,[32][33][34][35][36][37][38].…”

Section: Introductionmentioning

confidence: 99%

1,3-Dipolar Cycloaddition Reactions of Azomethine Ylides with Carbonyl Dipolarophiles Yielding Oxazolidine Derivatives

Meyer

Ryan

2016

Molecules

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Abstract:We provide a comprehensive account of the 1,3-dipolar cycloaddition reactions of azomethine ylides with carbonyl dipolarophiles. Many different azomethine ylides have been studied, including stabilized and non-stabilized ylides. Of the carbonyl dipolarophiles, aldehydes including formaldehyde are the most studied, although there are now examples of cycloadditions with ketones, ketenes and carboxyl systems, in particular isatoic anhydrides and phthalic anhydrides. Intramolecular cycloadditions with esters can also occur under certain circumstances. The oxazolidine cycloadducts undergo a range of reactions triggered by the ring-opening of the oxazolidine ring system.

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Section: Introductionmentioning

confidence: 99%

1,3-Dipolar Cycloaddition Reactions of Azomethine Ylides with Carbonyl Dipolarophiles Yielding Oxazolidine Derivatives

Meyer

Ryan

2016

Molecules

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“…The vast array of available 1,3-dipolar cycloadditions [1,2] providesg eneral andd irecta ccesst of ive-membered heterocycles [3], typically offering high levels of regio-and stereocontrol [4][5][6]. In previous studies, we have reported as eries of enantiomerically pure a-amino acids and enantiopure long-chain threo-2-amino-3-hydroxyesters by diastereo-controlled 1,3-dipolar cycloaddition between azomethine ylid derivatives of (5R)-5-phenylmorpholin-2-one and alkylation chemistry on the 3,4-dehydro derivatives [7][8][9].…”

Section: Discussionmentioning

confidence: 99%

Crystal structure of N-propynoyl-(5R)- 5-phenylmorpholin-2-one, C13H11NO3

Min-dong¹,

Xiao²,

Gong³

2012

Zeitschrift Für Kristallographie - New Crystal Structures

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Source of material Propiolicacid(0.21 g, 3mmol) was added to asolution of (5R)-5-phenylmorpholin-2-one (0.53 g, 3m mol) in anhydrous CH 2 Cl 2 (40 mL), and then dicyclohexylcarbodiimide (0.68 g, 3.3 mmol) in anhydrous CH 2 Cl 2 (10 mL) was addedo ver 10 min. The resulting solution was stirred for 12 h. The solid was removed by filtration through ashort pad of Celite and washed with CH 2 Cl 2 (10 mL). The solvent was removed under reduced pressure and the crude material was purified by flash columnchromatography on silica, eluting with PE-EtOAc (3:1) to furnish the title compound as colorlessneedles (1.81 g, yield 84 %; m.p. 125-126°C;[a] D 20 =-50.5, c=1.08, CHCl 3 ). IR, NMR and MS data are available in the CIF file. Experimental detailsAllthe hydrogen atoms were included in calculated positions and treated as riding with. Thea bsolute structure was confirmed with the Flack parameter of 0.016(8). DiscussionThe vast array of available 1,3-dipolar cycloadditions [1,2] providesg eneral andd irecta ccesst of ive-membered heterocycles [3], typically offering high levels of regio-and stereocontrol [4][5][6]. In previous studies, we have reported as eries of enantiomerically pure a-amino acids and enantiopure long-chain threo-2-amino-3-hydroxyesters by diastereo-controlled 1,3-dipolar cycloaddition between azomethine ylid derivatives of (5R)-5-phenylmorpholin-2-one and alkylation chemistry on the 3,4-dehydro derivatives [7][8][9]. Our ongoing interests in azide 1,3-dipolar cycloadditions of this template [10] resulted in the isolation of the title compound. The crystal structure of the title compound is built up of C 13 H 11 NO 3 molecules containing ab enzene and am orpholine ring. The morpholine heterocyclic ring exhibits boat-like conformation. The torsion angles are -12.5(2)°and -16.4(2)°for C9-C10-O1-C7 and C10-C9-N1-C8,respectively, andthe dihedral angle between them is 18.

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“…As a matter of fact, those compounds are found in a large number of best-selling pharmaceuticals and numerous synthetic pathways to access them are reported in the literature and full mention of the corresponding literature is beyond the scope of this work [7][8][9][10][11][12][13][14] . Needless to say that many synthetic approaches are described in the literature providing azomethine ylides [15][16][17][18][19][20][21][22][23][24] , but their overview is beyond the scope of this work. However thermolysis of aziridines, as exemplified by literature as regards the stereochemical synthesis of natural products 25,26 was more affordable to us in order to access the targeted ylides and involve them in the cycloaddition reaction.…”

Section: Introductionmentioning

confidence: 99%

1,3-Dipolar cycloaddition of azomethine ylide from Phtaloylimidophenylalanyl-2-hydroxymethylaziridine

et al. 2013

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Phtaloylimidophenylalanyl-2-hydroxymethylaziridine has been used as a starting material to yield azomethine ylide through thermal opening and was then involved into 1,3-dipolar cycloaddition reactions.Different five-membered adducts were obtained and were fully identified. The latter might be considered useful starting materials for further functionalization to provide novel compounds of biological interest.

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Chiral catalysts in the stereoselective synthesis of pyrrolidine derivatives via metallo-azomethine ylides

Cited by 188 publications

References 75 publications

1,3-Dipolar Cycloaddition Reactions of Azomethine Ylides with Carbonyl Dipolarophiles Yielding Oxazolidine Derivatives

1,3-Dipolar Cycloaddition Reactions of Azomethine Ylides with Carbonyl Dipolarophiles Yielding Oxazolidine Derivatives

Crystal structure of N-propynoyl-(5R)- 5-phenylmorpholin-2-one, C13H11NO3

1,3-Dipolar cycloaddition of azomethine ylide from Phtaloylimidophenylalanyl-2-hydroxymethylaziridine

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