Catalytic, Three-Component Assembly Reaction for the Synthesis of Pyrrolidines

Copper(I) salts catalyze the three-component assembly reaction between an α-diazo ester, an imine, and various alkenes and alkynes to form substituted pyrrolidines with excellent to good diastereoselectivities in high yields. The transition metal-catalyzed decomposition of the α-diazo compound in th...

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Bibliographic Details
Published in:Organic letters 2003-09, Vol.5 (19), p.3487-3490
Main Authors: Galliford, Chris V, Beenen, Melissa A, Nguyen, SonBinh T, Scheidt, Karl A
Format: Article
Language:English
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Summary:Copper(I) salts catalyze the three-component assembly reaction between an α-diazo ester, an imine, and various alkenes and alkynes to form substituted pyrrolidines with excellent to good diastereoselectivities in high yields. The transition metal-catalyzed decomposition of the α-diazo compound in the presence of the imine likely generates a transient azomethine ylid that undergoes addition with various dipolarophiles in a highly convergent manner.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol035292y