Literature DB >> 19371081

Regio- and stereoselective isomerizations of allenamides: synthesis of 2-amido-dienes and their tandem isomerization-electrocyclic ring-closure.

Ryuji Hayashi1, Richard P Hsung, John B Feltenberger, Andrew G Lohse.   

Abstract

A regio- and stereoselective isomerization of allenamides is described, leading to preparations of de novo 2-amido-dienes and a tandem isomerization-6pi-electron electrocyclic ring-closure.

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Year:  2009        PMID： 19371081      PMCID： PMC2732350          DOI： 10.1021/ol900647s

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


  23 in total

1.  Design and development of highly effective Lewis acid catalysts for enantioselective Diels-Alder reactions.

Authors:  Yong Huang; Tetsuo Iwama; Viresh H Rawal
Journal:  J Am Chem Soc       Date:  2002-05-29       Impact factor: 15.419

2.  Enamide-olefin ring-closing metathesis.

Authors:  S S Kinderman; J H van Maarseveen; H E Schoemaker; H Hiemstra; F P Rutjes
Journal:  Org Lett       Date:  2001-06-28       Impact factor: 6.005

3.  Total synthesis and absolute stereochemical assignment of (+)- and (-)-galbulimima alkaloid 13.

Authors:  Mohammad Movassaghi; Diana K Hunt; Meiliana Tjandra
Journal:  J Am Chem Soc       Date:  2006-06-28       Impact factor: 15.419

4.  Synthesis of allenamides by copper-catalyzed coupling of allenyl halides with amides, carbamates, and ureas.

Authors:  Barry M Trost; Dylan T Stiles
Journal:  Org Lett       Date:  2005-05-26       Impact factor: 6.005

5.  Computational studies on the electrocyclizations of 1-amino-1,3,5-hexatrienes.

Authors:  Vildan Adar Guner; K N Houk; Ian W Davies
Journal:  J Org Chem       Date:  2004-11-12       Impact factor: 4.354

6.  Retro-Ene Reactions in Acylallene Derivatives.

Authors:  Hervé Bibas; Rainer Koch; Curt Wentrup
Journal:  J Org Chem       Date:  1998-04-17       Impact factor: 4.354

7.  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

8.  Gold(I)-catalyzed isomerization of allenyl carbinol esters: an efficient access to functionalized 1,3-butadien-2-ol esters.

Authors:  Andrea K Buzas; Florin M Istrate; Fabien Gagosz
Journal:  Org Lett       Date:  2007-02-13       Impact factor: 6.005

9.  Copper-catalyzed stereospecific N-allenylations of amides. Syntheses of optically enriched chiral allenamides.

Authors:  Lichun Shen; Richard P Hsung; Yanshi Zhang; Jennifer E Antoline; Xuejun Zhang
Journal:  Org Lett       Date:  2005-07-07       Impact factor: 6.005

10.  Copper-mediated synthesis of N-acyl vinylogous carbamic acids and derivatives: synthesis of the antibiotic CJ-15,801.

Authors:  Chong Han; Ruichao Shen; Shun Su; John A Porco
Journal:  Org Lett       Date:  2004-01-08       Impact factor: 6.005
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  11 in total

1.  A tandem 1,3-H-shift-6π-electrocyclization-cyclic 2-amido-diene intramolecular Diels-Alder cycloaddition approach to BCD-Ring of atropurpuran.

Authors:  Ryuji Hayashi; Zhi-Xiong Ma; Richard P Hsung
Journal:  Org Lett       Date:  2011-12-13       Impact factor: 6.005

2.  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

3.  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

4.  Oppolzer-type intramolecular Diels-Alder cycloadditions via isomerizations of allenamides.

Authors:  John B Feltenberger; Richard P Hsung
Journal:  Org Lett       Date:  2011-05-25       Impact factor: 6.005

5.  A highly stereoselective Diels-Alder cycloaddition of enones with chiral cyclic 2-amidodienes derived from allenamides.

Authors:  Li-Chao Fang; Richard P Hsung; Zhi-Xiong Ma; William R Presser
Journal:  Org Lett       Date:  2013-09-03       Impact factor: 6.005

6.  Facile Synthesis of 3-Amido-Dienynes via a Tandem α-Propargylation-Isomerization of Chiral Allenamides and their Applications in Diels-Alder Cycloadditions.

Authors:  Zhi-Xiong Ma; Li-Chao Fang; Richard P Hsung
Journal:  Synlett       Date:  2017-09-01       Impact factor: 2.454

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

Authors:  Andrew G Lohse; Richard P Hsung
Journal:  Org Lett       Date:  2009-08-06       Impact factor: 6.005

Review 8.  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

9.  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

10.  Stereoselective synthesis of isoquinuclidines through an aza-[4 + 2] cycloaddition of chiral cyclic 2-amidodienes.

Authors:  Li-Chao Fang; Richard P Hsung
Journal:  Org Lett       Date:  2014-03-12       Impact factor: 6.005
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