Literature DB >> 12967306

Catalytic, three-component assembly reaction for the synthesis of pyrrolidines.

Chris V Galliford1, Melissa A Beenen, SonBinh T Nguyen, Karl A Scheidt.   

Abstract

[reaction: see text] Copper(I) salts catalyze the three-component assembly reaction between an alpha-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 alpha-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.

Entities:  

Year:  2003        PMID: 12967306     DOI: 10.1021/ol035292y

Source DB:  PubMed          Journal:  Org Lett        ISSN: 1523-7052            Impact factor:   6.005


  3 in total

1.  Cu(I)-catalyzed direct addition and asymmetric addition of terminal alkynes to imines.

Authors:  Chunmei Wei; Joel T Mague; Chao-Jun Li
Journal:  Proc Natl Acad Sci U S A       Date:  2004-04-05       Impact factor: 11.205

2.  Microwave-assisted Piloty-Robinson synthesis of 3,4-disubstituted pyrroles.

Authors:  Benjamin C Milgram; Katrine Eskildsen; Steven M Richter; W Robert Scheidt; Karl A Scheidt
Journal:  J Org Chem       Date:  2007-04-14       Impact factor: 4.354

3.  Asymmetric synthesis of trans-2,5-disubstituted pyrrolidines from enantiopure homoallylic amines. Synthesis of pyrrolidine (-)-197B.

Authors:  Franklin A Davis; Minsoo Song; Alexander Augustine
Journal:  J Org Chem       Date:  2006-03-31       Impact factor: 4.354

  3 in total

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