Literature DB >> 16986937

Asymmetric multicomponent reactions: diastereoselective synthesis of substituted pyrrolidines and prolines.

Arun K Ghosh1, Sarang Kulkarni, Chun-Xiao Xu, Phillip E Fanwick.   

Abstract

A novel diastereoselective synthesis of substituted pyrrolidines has been developed. Asymmetric multicomponent reactions of optically active phenyldihydrofuran, N-tosyl imino ester, and silane reagents in a one-pot operation afforded highly substituted pyrrolidine derivatives diastereoselectively. The reaction is quite efficient and constructed up to three stereogenic centers in a single operation.

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Year:  2006        PMID： 16986937      PMCID： PMC3179855          DOI： 10.1021/ol061672i

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


  14 in total

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6.  Potent HIV protease inhibitors incorporating high-affinity P2-ligands and (R)-(hydroxyethylamino)sulfonamide isostere.

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7.  Stereoselective synthesis of constrained azacyclic hydroxyethylene isosteres as aspartic protease inhibitors: dipolar cycloaddition and related methodologies toward branched pyrrolidine and pyrrolidinone carboxylic acids.

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8.  Synthesis of highly functionalized pyrrolidines via a mild one-pot, three-component 1,3-dipolar cycloaddition process.

Authors:  Philip Garner; H Umit Kaniskan
Journal:  J Org Chem       Date:  2005-12-23       Impact factor: 4.354

9.  Asymmetric synthesis of polyfunctionalized pyrrolidines from sulfinimine-derived pyrrolidine 2-phosphonates. Synthesis of pyrrolidine 225C.

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  6 in total

1.  Highly diastereoselective synthesis of modified nucleosides via an asymmetric multicomponent reaction.

Authors:  Arun K Ghosh; Jorden Kass
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2.  Asymmetric multi-component reactions: convenient access to acyclic stereocenters and functionalized cyclopentenoids.

Authors:  Arun K Ghosh; Sarang S Kulkarni; Chun-Xiao Xu; Khriesto Shurrush
Journal:  Tetrahedron Asymmetry       Date:  2008-05-01

3.  TiCl4-promoted tandem carbonyl or imine addition and Friedel-Crafts cyclization: synthesis of benzo-fused oxabicyclooctanes and nonanes.

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Journal:  Org Lett       Date:  2012-04-04       Impact factor: 6.005

4.  A stereoselective synthesis of (-)-viridiofungin A utilizing a TiCl(4)-promoted asymmetric multicomponent reaction.

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Journal:  Org Lett       Date:  2011-12-23       Impact factor: 6.005

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  6 in total

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