Literature DB >> 15225048

Catalytic generation of activated carboxylates: direct, stereoselective synthesis of beta-hydroxyesters from epoxyaldehydes.

Kenneth Yu-Kin Chow1, Jeffrey W Bode.   

Abstract

The catalytic generation of activated carboxylates from epoxyaldehydes enables the direct, stereoselective synthesis of beta-hydroxyesters under mild, convenient reaction conditions. In addition to providing a new method for the synthesis of anti-aldol adducts, this chemistry unveils a mechanistically viable solution to the catalytic, waste-free synthesis of esters.

Entities:  

Year:  2004        PMID: 15225048     DOI: 10.1021/ja047407e

Source DB:  PubMed          Journal:  J Am Chem Soc        ISSN: 0002-7863            Impact factor:   15.419


  28 in total

1.  Rapid and stereochemically flexible synthesis of polypropionates: super-silyl-governed aldol cascades.

Authors:  Patrick B Brady; Hisashi Yamamoto
Journal:  Angew Chem Int Ed Engl       Date:  2012-01-17       Impact factor: 15.336

2.  A formal synthesis of the C1-C9 fragment of amphidinolide C employing the Tamaru reaction.

Authors:  Mahesh P Paudyal; Nigam P Rath; Christopher D Spilling
Journal:  Org Lett       Date:  2010-07-02       Impact factor: 6.005

Review 3.  Carbene catalysts.

Authors:  Jennifer L Moore; Tomislav Rovis
Journal:  Top Curr Chem       Date:  2010

4.  Chiral N-heterocyclic carbene-catalyzed generation of ester enolate equivalents from {alpha},{beta}-unsaturated aldehydes for enantioselective Diels-Alder reactions.

Authors:  Juthanat Kaeobamrung; Marisa C Kozlowski; Jeffrey W Bode
Journal:  Proc Natl Acad Sci U S A       Date:  2010-10-25       Impact factor: 11.205

5.  Carbene catalysis: An internal affair.

Authors:  Jeffrey W Bode
Journal:  Nat Chem       Date:  2013-10       Impact factor: 24.427

6.  Nucleophilic carbene and HOAt relay catalysis in an amide bond coupling: an orthogonal peptide bond forming reaction.

Authors:  Harit U Vora; Tomislav Rovis
Journal:  J Am Chem Soc       Date:  2007-10-11       Impact factor: 15.419

Review 7.  Organocatalytic Reactions Enabled by N-Heterocyclic Carbenes.

Authors:  Darrin M Flanigan; Fedor Romanov-Michailidis; Nicholas A White; Tomislav Rovis
Journal:  Chem Rev       Date:  2015-05-20       Impact factor: 60.622

8.  Exploiting Acyl and Enol Azolium Intermediates via NHeterocyclic Carbene Catalyzed Reactions of Alpha-Reducible Aldehydes.

Authors:  Harit U Vora; Philip Wheeler; Tomislav Rovis
Journal:  Adv Synth Catal       Date:  2012-04-19       Impact factor: 5.837

9.  Nucleophilic carbene catalyzed synthesis of 1,2 amino alcohols via azidation of epoxy aldehydes.

Authors:  Harit U Vora; Johannah R Moncecchi; Oleg Epstein; Tomislav Rovis
Journal:  J Org Chem       Date:  2008-12-19       Impact factor: 4.354

Review 10.  A continuum of progress: applications of N-hetereocyclic carbene catalysis in total synthesis.

Authors:  Javier Izquierdo; Gerri E Hutson; Daniel T Cohen; Karl A Scheidt
Journal:  Angew Chem Int Ed Engl       Date:  2012-10-16       Impact factor: 15.336

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