Literature DB >> 21090590

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

Ryuji Hayashi1, Mary C Walton, Richard P Hsung, John H Schwab, Xueliang Yu.   

Abstract

A diastereoselective 6π-electrocyclic ring closure employing halogen-substituted 3-amidotrienes via a 1,6-remote asymmetric induction is described. This new asymmetric manifold for pericyclic ring closure further underscores the significance of the allenamide chemistry.

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Year:  2010        PMID： 21090590      PMCID： PMC3010762          DOI： 10.1021/ol102693e

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


  36 in total

1.  Oxidation of alpha-alkoxy allenes into alpha'-alkoxy enones.

Authors:  Pierre Cordier; Corinne Aubert; Max Malacria; Vincent Gandon; Emmanuel Lacôte
Journal:  Chemistry       Date:  2010-09-03       Impact factor: 5.236

2.  Regioselectivities of (4 + 3) cycloadditions between furans and oxazolidinone-substituted oxyallyls.

Authors:  Andrew G Lohse; Elizabeth H Krenske; Jennifer E Antoline; K N Houk; Richard P Hsung
Journal:  Org Lett       Date:  2010-11-04       Impact factor: 6.005

3.  Palladium-catalyzed [3,3]-rearrangement for the facile synthesis of allenamides.

Authors:  Amy M Danowitz; Christopher E Taylor; Tamar M Shrikian; Anna K Mapp
Journal:  Org Lett       Date:  2010-06-04       Impact factor: 6.005

4.  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

5.  Tunable Pd-catalyzed cyclization of indole-2-carboxylic acid allenamides: carboamination vs microwave-assisted hydroamination.

Authors:  Egle M Beccalli; Alice Bernasconi; Elena Borsini; Gianluigi Broggini; Micol Rigamonti; Gaetano Zecchi
Journal:  J Org Chem       Date:  2010-10-15       Impact factor: 4.354

6.  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

7.  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

8.  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

9.  Biomimetic synthesis of the shimalactones.

Authors:  Vladimir Sofiyev; Gabriel Navarro; Dirk Trauner
Journal:  Org Lett       Date:  2007-12-12       Impact factor: 6.005

10.  Remarkably mild and efficient intramolecular Friedel-Crafts cyclization catalyzed by In(III).

Authors:  Ryuji Hayashi; Gregory R Cook
Journal:  Org Lett       Date:  2007-03-09       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.  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

3.  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

4.  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

5.  A torquoselective 6π electrocyclization approach to reserpine alkaloids.

Authors:  Gregg A Barcan; Ashay Patel; K N Houk; Ohyun Kwon
Journal:  Org Lett       Date:  2012-10-05       Impact factor: 6.005

6.  Origins of 1,6-stereoinduction in torquoselective 6π electrocyclizations.

Authors:  Ashay Patel; Gregg A Barcan; Ohyun Kwon; K N Houk
Journal:  J Am Chem Soc       Date:  2013-03-18       Impact factor: 15.419

7.  α-Aryl-substituted allenamides in an imino-Nazarov cyclization cascade catalyzed by Au(I).

Authors:  Zhi-Xiong Ma; Shuzhong He; Wangze Song; Richard P Hsung
Journal:  Org Lett       Date:  2012-11-02       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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