Literature DB >> 19591454

Thermal intramolecular [4 + 2] cycloadditions of allenamides: a stereoselective tandem propargyl amide isomerization-cycloaddition.

Andrew G Lohse1, Richard P Hsung.   

Abstract

A stereoselective intramolecular normal demand [4 + 2] cycloaddition of allenamides under thermal conditions without metal assistance is described. This work led to the development of a stereoselective tandem propargyl amide-isomerization-[4 + 2] cycloaddition sequence amenable for rapid assembly of complex nitrogen heterocycles.

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Year:  2009        PMID： 19591454      PMCID： PMC2736324          DOI： 10.1021/ol901283m

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


  22 in total

1.  Facile synthesis of the tricyclic core of sarain A. 3-Oxidopyridinium betaine cycloaddition approach.

Authors:  M J Sung; H I Lee; Y Chong; J K Cha
Journal:  Org Lett       Date:  1999-12-16       Impact factor: 6.005

2.  Platinum-catalyzed intramolecular [4C+3C] cycloaddition between dienes and allenes.

Authors:  Beatriz Trillo; Fernando López; Moisés Gulías; Luis Castedo; José L Mascareñas
Journal:  Angew Chem Int Ed Engl       Date:  2008       Impact factor: 15.336

3.  Gold catalysis: no steric limitations in the phenol synthesis.

Authors:  A Stephen K Hashmi; Ralph Salathé; Wolfgang Frey
Journal:  Chemistry       Date:  2006-09-06       Impact factor: 5.236

4.  Chiral Lewis acid-catalyzed highly enantioselective [4 + 3] cycloaddition reactions of nitrogen-stabilized oxyallyl cations derived from allenamides.

Authors:  Jian Huang; Richard P Hsung
Journal:  J Am Chem Soc       Date:  2005-01-12       Impact factor: 15.419

5.  The first regioselective alpha-deprotonation and functionalization of allenamides. An application in intramolecular Pauson-Khand-type cycloadditions.

Authors:  H Xiong; R P Hsung; L L Wei; C R Berry; J A Mulder; B Stockwell
Journal:  Org Lett       Date:  2000-09-07       Impact factor: 6.005

6.  Asymmetric organocatalysis of 4 + 3 cycloaddition reactions.

Authors:  Michael Harmata; Sunil K Ghosh; Xuechuan Hong; Sumrit Wacharasindhu; Patrick Kirchhoefer
Journal:  J Am Chem Soc       Date:  2003-02-26       Impact factor: 15.419

7.  Stereoselective intramolecular [4 + 3] cycloadditions of nitrogen-stabilized chiral oxyallyl cations via epoxidation of N-tethered allenamides.

Authors:  Hui Xiong; Jian Huang; Sunil K Ghosh; Richard P Hsung
Journal:  J Am Chem Soc       Date:  2003-10-22       Impact factor: 15.419

8.  Palladium-catalyzed domino carbopalladation/5-exo-allylic amination of alpha-amino allenamides: an efficient entry to enantiopure imidazolidinones.

Authors:  Egle M Beccalli; Gianluigi Broggini; Francesca Clerici; Simona Galli; Claire Kammerer; Micol Rigamonti; Silvia Sottocornola
Journal:  Org Lett       Date:  2009-04-02       Impact factor: 6.005

9.  A tandem epoxidation/stereoselective intramolecular [4+3] cycloaddition reaction involving nitrogen-stabilized oxyallyl cations derived from chiral allenamides.

Authors:  Challeppan Rameshkumar; Richard P Hsung
Journal:  Angew Chem Int Ed Engl       Date:  2004-02-01       Impact factor: 15.336

10.  Catalytic carbophilic activation: catalysis by platinum and gold pi acids.

Authors:  Alois Fürstner; Paul W Davies
Journal:  Angew Chem Int Ed Engl       Date:  2007       Impact factor: 15.336
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  6 in total

1.  Torquoselective ring closures of chiral amido trienes derived from allenamides. A tandem allene isomerization-pericyclic ring-closure-intramolecular Diels-Alder cycloaddition.

Authors:  Ryuji Hayashi; John B Feltenberger; Richard P Hsung
Journal:  Org Lett       Date:  2010-03-19       Impact factor: 6.005

2.  Stereoselective 6π-electron electrocyclic ring closures of 2-halo-amidotrienes via a remote 1,6-asymmetric induction.

Authors:  Ryuji Hayashi; Mary C Walton; Richard P Hsung; John H Schwab; Xueliang Yu
Journal:  Org Lett       Date:  2010-11-19       Impact factor: 6.005

3.  Developing a diastereoselective intramolecular [4+3] cycloaddition of nitrogen-stabilized oxyallyl cations derived from N-sulfonyl-substituted allenamides.

Authors:  Andrew G Lohse; Richard P Hsung; Mitchell D Leider; Sunil K Ghosh
Journal:  J Org Chem       Date:  2011-04-08       Impact factor: 4.354

Review 4.  Allenamides: a powerful and versatile building block in organic synthesis.

Authors:  Ting Lu; Zhenjie Lu; Zhi-Xiong Ma; Yu Zhang; Richard P Hsung
Journal:  Chem Rev       Date:  2013-04-04       Impact factor: 60.622

5.  An efficient and practical entry to 2-amido-dienes and 3-amido-trienes from allenamides through stereoselective 1,3-hydrogen shifts.

Authors:  Ryuji Hayashi; John B Feltenberger; Andrew G Lohse; Mary C Walton; Richard P Hsung
Journal:  Beilstein J Org Chem       Date:  2011-04-07       Impact factor: 2.883

6.  (3aR,6S,7aR)-7a-Bromo-2-[(4-methyl-phen-yl)sulfon-yl]-1,2,3,6,7,7a-hexa-hydro-3a,6-ep-oxy-isoindole.

Authors:  Başak Koşar; Aydın Demircan; Hakan Arslan; Orhan Büyükgüngör
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2011-03-31
  6 in total

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