Unusually Reactive and Selective Carbonyl Ylides for Three-Component Cycloaddition Reactions
نویسندگان
چکیده
منابع مشابه
1,3-Dipolar Cycloaddition Reactions of Azomethine Ylides with Carbonyl Dipolarophiles Yielding Oxazolidine Derivatives.
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 carbo...
متن کاملA novel synthesis of diastereomerically pure spiro- oxindolopyrrolizidines and oxindolopyrrolidines via cycloaddition reactions of azomethine ylides
An efficient one-pot three-component procedure for the synthesis of new chiral spiro oxindolopyrrolidines/pyrrolizidines with highly regio- and diastereo-enantio, selective from 1,3-dipolar cycloaddition of azomethine ylides and chiral menthol-drived trans-cinnamic are described. The mechanism of the reaction is discussed on basis of the assignment of the absolute configuration of one of the cy...
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...
متن کاملExperimental and theoretical study of the [3 + 2] cycloaddition of carbonyl ylides with alkynes.
The [3 + 2] cycloaddition reaction between carbonyl ylides generated from epoxides and alkynes (phenylacetylene, methyl propiolate, methyl but-2-ynoate and methyl 3-phenylpropiolate) to give substituted 2,5-dihydrofurans was investigated. The effect of indium(III) chloride on the outcome of the reaction was studied in the case of phenylacetylene and methyl propiolate. The thermal reaction betwe...
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: Journal of the American Chemical Society
سال: 2009
ISSN: 0002-7863,1520-5126
DOI: 10.1021/ja807184r