Literature DB >> 11784169

Tandem chain extension-aldol reaction: syn selectivity with a zinc enolate.

S Lai1, C K Zercher, J P Jasinski, S N Reid, R J Staples.   

Abstract

A tandem chain extension-aldol reaction was developed in which beta-keto esters are transformed to alpha-substituted-gamma-keto esters in an efficient zinc-mediated, one-pot reaction. The diastereoselectivity of the reaction ranged from good to excellent with syn stereochemistry observed for beta-keto ester and amide substrates and anti-stereochemistry observed for a beta-keto imide. [reaction: see text]

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Year:  2001        PMID: 11784169     DOI: 10.1021/ol016788n

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


  8 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.  The tandem chain extension aldol reaction used for synthesis of ketomethylene tripeptidomimetics targeting hPEPT1.

Authors:  Karina Thorn; Carsten Uhd Nielsen; Palle Jakobsen; Bente Steffansen; Charles K Zercher; Mikael Begtrup
Journal:  Bioorg Med Chem Lett       Date:  2011-06-06       Impact factor: 2.823

3.  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

4.  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

5.  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

6.  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

7.  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

8.  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

  8 in total

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