Literature DB >> 21428300

Gosteli-Claisen rearrangement of propargyl vinyl ethers: cascading molecular rearrangements.

Annika Gille1, Julia Rehbein, Martin Hiersemann.   

Abstract

The ambivalent reactivity of 2-alkoxycarbonyl-substituted propargyl vinyl ethers has been explored. Depending on the conditions, the catalyzed and uncatalyzed Gosteli-Claisen rearrangement triggers downstream transformations that cascade from initially formed γ-allenyl α-keto esters to highly substituted furanes and cyclopentenes. In support of a mechanistic hypothesis, the results of a DFT study using the B1B95 and B3LYP functionals are revealed.
© 2011 American Chemical Society

Entities:  

Year:  2011        PMID： 21428300     DOI： 10.1021/ol200558j

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


  3 in total

1.  Chiral N-Heterocyclic Carbene Catalyzed Annulations of Enals and Ynals with Stable Enols: A Highly Enantioselective Coates-Claisen Rearrangement.

Authors:  Jessada Mahatthananchai; Juthanat Kaeobamrung; Jeffrey W Bode
Journal:  ACS Catal       Date:  2012-02-29       Impact factor: 13.084

2.  Crystal structure of (E)-N'-{[(1R,3R)-3-isopropyl-1-methyl-2-oxo-cyclo-pent-yl]methyl-idene}-4-methyl-benzene-sulfono-hydrazide.

Authors:  David Tymann; Dina Christina Dragon; Christopher Golz; Hans Preut; Carsten Strohmann; Martin Hiersemann
Journal:  Acta Crystallogr E Crystallogr Commun       Date:  2015-01-10

3.  Crystal structure of N'-[(E)-(1S,3R)-(3-isopropyl-1-methyl-2-oxo-cyclo-pent-yl)methyl-idene]-4-methyl-benzene-sulfono-hydrazide.

Authors:  David Tymann; Dina Christina Dragon; Christopher Golz; Hans Preut; Carsten Strohmann; Martin Hiersemann
Journal:  Acta Crystallogr E Crystallogr Commun       Date:  2015-11-04
  3 in total

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