three-component procedure for the synthesis chiral spirooxindolopyrrolizidines via catalytic highly enantioselective 1,3-dipolar cycloaddition of azomethineylides and 3-(2-alkenoyl)-1,3-oxazolidin-2-ones

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چکیده

the catalytic highly regio-, diastereo-, and enantioselective synthesis of a small library of spiropyrrolizidineoxindolesvia a four-component 1,3-dipolar cycloaddition reactionof azomethineylides, derived from isatin, with electron-deficient dipolarophilewas described. the process occurs at room temperature in aqueous ethanol as a green solvent and in the presence of a bidendatebis(imine)–cu(ii)triflate complex as catalyst.the reaction mechanism is discussedon the basis of the assignment of the absolute configuration of the cycloadducts.

منابع مشابه

Three-Component Procedure for the Synthesis Chiral Spirooxindolopyrrolizidines via Catalytic Highly Enantioselective 1,3-Dipolar Cycloaddition of Azomethineylides and 3-(2-Alkenoyl)-1,3-Oxazolidin-2-ones

The catalytic highly regio-, diastereo-, and enantioselective synthesis of a small library of spiropyrrolizidineoxindolesvia a four-component 1,3-dipolar cycloaddition reactionof azomethineylides, derived from isatin, with electron-deficient dipolarophilewas described. The process occurs at room temperature in aqueous ethanol as a green solvent and in the presence of a bidendatebis(imi...

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Three-Component Procedure for the Synthesis Chiral Spirooxindolopyrrolizidines via Catalytic Highly Enantioselective 1,3-Dipolar Cycloaddition of Azomethineylides and 3-(2-Alkenoyl)-1,3-Oxazolidin-2-ones

The catalytic highly regio-, diastereo-, and enantioselective synthesis of a small library of spiropyrrolizidineoxindolesvia a four-component 1,3-dipolar cycloaddition reactionof azomethineylides, derived from isatin, with electron-deficient dipolarophilewas described. The process occurs at room temperature in aqueous ethanol as a green solvent and in the presence of a bidendatebis(imi...

متن کامل

Three-component procedure for the synthesis of new chiral spirooxindolopyrrolizidines via catalytic highly enantioselective 1,3-dipolar cycloaddition

The catalytic highly regio-, diastereo-, and enantioselective synthesis of a small library of spiropyrrolizidineoxindolesvia a four-component 1,3-dipolar cycloaddition reaction of azomethine ylides, derived from isatin, with electron-deficient dipolarophilewas described. The process occurs at room temperature in aqueous ethanol as a green solvent and in the presence of a bidendatebis(imine)–Cu(...

متن کامل

three-component procedure for the synthesis of new chiral spirooxindolopyrrolizidines via catalytic highly enantioselective 1,3-dipolar cycloaddition

the catalytic highly regio-, diastereo-, and enantioselective synthesis of a small library of spiropyrrolizidineoxindolesvia a four-component 1,3-dipolar cycloaddition reaction of azomethine ylides, derived from isatin, with electron-deficient dipolarophilewas described. the process occurs at room temperature in aqueous ethanol as a green solvent and in the presence of a bidendatebis(imine)–cu(...

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An Efficient and One-pot Procedure for the Synthesis of Chiral Isoxazolidine via Catalytic Highly Enantioselective 1,3-dipolar cycloaddition

Synthesis of enantiomerically pure isoxazolidine via an asymmetric 1,3- dipolar cycloaddition reaction of nitrone with electron-deficient dipolarophile was described. The process occurs at room temperature in aqueous ethanol as a green solvent and in the presence of a bidendate bis(imine)–Cu(II)triflate complex as catalyst. The reaction mechanism is discussed on the basis of the assignment of t...

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Chiral bifunctional ferrocenylphosphine catalyzed highly enantioselective [3 + 2] cycloaddition reaction.

A series of air-stable ferrocenylphosphines LB1-LB8 were designed and prepared in high yields. (R,SFc)-ferrocenylphosphine LB5 was found to efficiently promote the asymmetric [3 + 2] cycloaddition of Morita-Baylis-Hillman carbonates with maleimides to afford the corresponding bicyclic imides with 84-99% ee and 67-99% yield. Interestingly, the configuration of these products was contrary to thos...

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عنوان ژورنال:
international journal of bio-inorganic hybrid nanomaterials

جلد ۲، شماره ۴، صفحات ۵۰۳-۵۱۰

کلمات کلیدی
[ ' c h i r a l s p i r o ' , ' o x i n d o l o p y r r o l i z i d i n e s ' , ' a s y m m e t r i c 1 ' , 3 , ' d i p o l a r ' , ' c h i r a l a u x i l i a r i e s ' , ' a z o m e t h i n e y l i d e ' , ' t h r e e ' , ' c o m p o n e n t r e a c t i o n ' , ' p r o l i n e ' , ' s a r c o s i n e ' ]

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