Literature DB >> 25083751

Cyclopentanoids by uncatalyzed intramolecular carbonyl ene (ICE) reaction of α-keto esters.

David Tymann1, André Klüppel, Wolf Hiller, Martin Hiersemann.   

Abstract

The uncatalyzed intramolecular carbonyl ene (ICE) reaction of substituted ε,ζ-unsaturated α-keto esters to terpenoid-related building blocks has been studied. We found a beneficial effect of a silyl substituent at the ene segment on the kinetics of the ICE reaction. A generalizable and scalable synthesis of ε,ζ-unsaturated α-keto esters from allylic alcohols was developed.

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Year:  2014        PMID： 25083751     DOI： 10.1021/ol501204m

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


  3 in total

1.  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

2.  Hybrid macrocycle formation and spiro annulation on cis-syn-cis-tricyclo[6.3.0.0(2,6)]undeca-3,11-dione and its congeners via ring-closing metathesis.

Authors:  Sambasivarao Kotha; Ajay Kumar Chinnam; Rashid Ali
Journal:  Beilstein J Org Chem       Date:  2015-07-06       Impact factor: 2.883

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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