Literature DB >> 15901148

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

Barry M Trost1, Dylan T Stiles.   

Abstract

[reaction: see text]. A variety of N-substituted allenes have been synthesized by the copper-catalyzed coupling reaction between allenyl halides and amides, carbamates, and ureas. The reactions proceed in good to excellent yield using 7 mol % copper thiophenecarboxylate and 15 mol % of a diamine catalyst.

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Year:  2005        PMID： 15901148     DOI： 10.1021/ol050395x

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


  13 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.  Palladium-catalyzed synthesis of N-vinyl pyrroles and indoles.

Authors:  Mohammad Movassaghi; Alison E Ondrus
Journal:  J Org Chem       Date:  2005-10-14       Impact factor: 4.354

5.  Diamine Ligands in Copper-Catalyzed Reactions.

Authors:  David S Surry; Stephen L Buchwald
Journal:  Chem Sci       Date:  2010       Impact factor: 9.825

6.  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

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

Authors:  Ryuji Hayashi; Richard P Hsung; John B Feltenberger; Andrew G Lohse
Journal:  Org Lett       Date:  2009-05-21       Impact factor: 6.005

8.  Saucy-Marbet Rearrangements of Alkynyl Halides in the Synthesis of Highly Enantiomerically Enriched Allenyl Halides.

Authors:  Yu Tang; Lichun Shen; Becky J Dellaria; Richard P Hsung
Journal:  Tetrahedron Lett       Date:  2008-11-03       Impact factor: 2.415

9.  Synthesis of amido-spiro[2.2]pentanes via Simmons-Smith cyclopropanation of allenamides.

Authors:  Ting Lu; Ryuji Hayashi; Richard P Hsung; Kyle A DeKorver; Andrew G Lohse; Zhenlei Song; Yu Tang
Journal:  Org Biomol Chem       Date:  2009-06-19       Impact factor: 3.876

10.  Allylic and allenic halide synthesis via NbCl(5)- and NbBr(5)-mediated alkoxide rearrangements.

Authors:  P C Ravikumar; Lihua Yao; Fraser F Fleming
Journal:  J Org Chem       Date:  2009-10-02       Impact factor: 4.354
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