Literature DB >> 11554837

Tandem chain extension-homoenolate formation: the formation of alpha-methylated-gamma-keto esters.

R Hilgenkamp1, C K Zercher.   

Abstract

A tandem chain extension-homoenolate formation reaction is described. The treatment of beta-keto esters with the Furukawa reagent followed by exposure to a catalytic amount of trimethylsilyl chloride provides access to an ester homoenolate. Reaction: see text.

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Year:  2001        PMID: 11554837     DOI: 10.1021/ol016485t

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


  7 in total

1.  A mechanistic investigation into the zinc carbenoid-mediated homologation reaction by DFT methods: is a classical donor-acceptor cyclopropane intermediate involved?

Authors:  Wilhelm A Eger; Charles K Zercher; Craig M Williams
Journal:  J Org Chem       Date:  2010-11-05       Impact factor: 4.354

2.  A combined DFT and NMR investigation of the zinc organometallic intermediate proposed in the syn-selective tandem chain extension-aldol reaction of β-keto esters.

Authors:  Karelle S Aiken; Wilhelm A Eger; Craig M Williams; Carley M Spencer; Charles K Zercher
Journal:  J Org Chem       Date:  2012-07-03       Impact factor: 4.354

3.  Syntheses of papyracillic acids: application of the tandem chain extension-acylation reaction.

Authors:  Jennifer R Mazzone; Charles K Zercher
Journal:  J Org Chem       Date:  2012-10-05       Impact factor: 4.354

4.  Tandem Homologation-Acylation Chemistry: Single and Double Homologation.

Authors:  Carley S Henderson; Jennifer R Mazzone; Amanda M Moore; Charles K Zercher
Journal:  Tetrahedron       Date:  2021-05-19       Impact factor: 2.388

5.  Stereoselective formation of a functionalized dipeptide isostere by zinc carbenoid-mediated chain extension.

Authors:  Weimin Lin; Cory R Theberge; Timothy J Henderson; Charles K Zercher; Jerry Jasinski; Ray J Butcher
Journal:  J Org Chem       Date:  2009-01-16       Impact factor: 4.354

6.  Tandem Chain Extension-Iodomethylation Reactions: Formation of alpha-Functionalized gamma-Keto Carbonyls.

Authors:  Qinglin Pu; Emerald Wilson; Charles K Zercher
Journal:  Tetrahedron       Date:  2008-08-25       Impact factor: 2.457

7.  Tandem chain extension-Mannich reaction: an approach to β-proline derivatives.

Authors:  Alexander M Jacobine; Angela L A Puchlopek; Charles K Zercher; Jon B Briggs; Jerry P Jasinski; Raymond J Butcher
Journal:  Tetrahedron       Date:  2012-07-17       Impact factor: 2.457

  7 in total

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