Stereochemical diversity in pyrrolidine synthesis by catalytic asymmetric 1,3-dipolar cycloaddition of azomethine ylides
نویسندگان
چکیده
منابع مشابه
Recent advances in the catalytic asymmetric 1,3-dipolar cycloaddition of azomethine ylides.
Catalytic asymmetric 1,3-dipolar cycloadditions of azomethine ylides have turned out to be one of the most efficient methods for the preparation of enantioenriched pyrrolidines. The past decade has witnessed the development of a bunch of well-defined catalytic systems capable of affording excellent diastereo and enantioselectivities. Recently, a great effort has been focused on expanding the sc...
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We report a new catalyst system that should enhance the use of enantioselective 1,3-dipolar cycloadditions of azomethine ylides with electronic-deficient olefins in the divergent pathways of diversity-oriented synthesis (DOS). The underlying reaction is of considerable interest in DOS because its stereospecificity enables stereochemical diversification of up to four tetrahedral centers on pyrro...
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[reaction: see text] A bifunctional AgOAc-catalyzed asymmetric cycloaddition of azomethine ylides with electronic-deficient alkenes was developed using ferrocenyloxazoline-derived N,P ligands. The reactive metal-bound azomethine ylide dipole is formed by the deprotonation with acetate, and extra base is not necessary. The reactions proceed with high enantioselectivity. This method provides an e...
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This review highlights the biological importance of many polysubstituted nitro-prolines and -pyrrolidines. Their preparation using asymmetric 1,3-dipolar cycloadditions of azomethine ylides with nitroalkenes using diastereoselective and enantioselective strategies is described remarking the scope and main features of each one.
متن کاملChiral Induction in Cycloaddition Reactions of Azomethine Ylides to Synthesis of New Enantiomerically Pure Spiro Oxindolopyrrolizidines
An efficient one-pot three-component procedure for the synthesis of new chiral spiro-oxindolopyrrolizidines with highly regio-, diastereo-, and enantioselective from 1,3-dipolar cycloaddition of azomethine ylides and optically pure active cinamoyl oxazolidinone are described. The process occurs at room temperature in aqueous ethanol as green solvent and in the absence of any bidentate chelating...
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ژورنال
عنوان ژورنال: Chemical Communications
سال: 2019
ISSN: 1359-7345,1364-548X
DOI: 10.1039/c9cc05238k