Asymmetric construction of trifluoromethylated pyrrolidines via Cu(I)-catalyzed 1,3-dipolar cycloaddition of azomethine ylides with 4,4,4-trifluorocrotonates.
نویسندگان
چکیده
Trifluoromethylated pyrrolidines have been synthesized via catalytic asymmetric 1,3-dipolar cycloaddition with excellent stereoselectivity for the first time. Epimerization of the endo-pyrrolidines obtained from cis-4,4,4-trifluorocrotonate into the exo-pyrrolidines was also revealed.
منابع مشابه
Asymmetric Synthesis of New Diastereomerically Pure Spiro Oxindolopyrrolizidines and Oxindolopyrrolidines via Cycloaddition Reactions of Azomethine Ylides and Menthol-Drived Trans-Cinnamic
Chiral pyrrolidines and pyrrolizidines with spirooxindole ring systems are the central skeletons for numerous alkaloids and pharmacologically important compounds. Gelesmine, pseudotabersonine, formosanine, isoformosanine, morroniside and mitraphylline are some of the alkaloids containing spirooxindole ring systems. Derivatives of spirooxindole find very wide biological applications as anti micr...
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Chiral pyrrolidines and pyrrolizidines with spirooxindole ring systems are the central skeletons for numerous alkaloids and pharmacologically important compounds. Gelesmine, pseudotabersonine, formosanine, isoformosanine, morroniside and mitraphylline are some of the alkaloids containing spirooxindole ring systems. Derivatives of spirooxindole find very wide biological applications as anti micr...
متن کاملA Three-Component 1,3-Dipolar Cycloaddition Reaction of Azomethine Ylide for Synthesis of New Bis-spiro-oxindolo(pyrrolizidines/pyrrolidines) Derivatives
The development of multicomponent reactions (MCRs) designed to produce elaborate biologically active compounds has become an important area of research in organic, combinatorial, and medicinal chemistry. A comparative study of the synthesis of new bis-spiro-oxindolo(pyrrolizidines/pyrrolidines) ring systems by the cycloaddition of azomethine ylides generated by a decarboxylative route from sarc...
متن کاملCu(I)-catalyzed highly exo-selective and enantioselective [3 + 2] cycloaddition of azomethine ylides with acrylates.
[reaction: see text] A novel Cu(I)-catalyzed asymmetric 1,3-dipolar cycloaddition of azomethine ylides with acrylates has been developed. Up to 98/2 exo/endo selectivity and up to 98% enantiomeric excess have been achieved.
متن کاملA Three-Component 1,3-Dipolar Cycloaddition Reaction of Azomethine Ylide for Synthesis of New Bis-spiro-oxindolo(pyrrolizidines/pyrrolidines) Derivatives
The development of multicomponent reactions (MCRs) designed to produce elaborate biologically active compounds has become an important area of research in organic, combinatorial, and medicinal chemistry. A comparative study of the synthesis of new bis-spiro-oxindolo(pyrrolizidines/pyrrolidines) ring systems by the cycloaddition of azomethine ylides generated by a decarboxylative route from sarc...
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ورودعنوان ژورنال:
- Chemical communications
دوره 47 39 شماره
صفحات -
تاریخ انتشار 2011