Literature DB >> 21278848

An Efficient Synthesis of de novo Imidates via Aza-Claisen Rearrangements of N-Allyl Ynamides.

Kyle A Dekorver1, Troy D North, Richard P Hsung.   

Abstract

A novel thermal 3-aza-Claisen rearrangement of N-allyl ynamides for the synthesis of α-allyl imidates is described. Also, a sequential aza-Claisen, Pd-catalyzed Overman rearrangement is described for the synthesis of azapine-2-ones.

Entities:  

Year:  2010        PMID： 21278848      PMCID： PMC3027154          DOI： 10.1055/s-0030-1258544

Source DB:  PubMed          Journal:  Synlett        ISSN： 0936-5214            Impact factor:   2.454


  23 in total

1.  Cu-catalyzed oxidative amidation of propiolic acids under air via decarboxylative coupling.

Authors:  Wei Jia; Ning Jiao
Journal:  Org Lett       Date:  2010-05-07       Impact factor: 6.005

2.  A divergent mechanistic course of Pd(0)-catalyzed aza-Claisen rearrangement and aza-Rautenstrauch-type cyclization of N-allyl ynamides.

Authors:  Kyle A Dekorver; Richard P Hsung; Andrew G Lohse; Yu Zhang
Journal:  Org Lett       Date:  2010-04-16       Impact factor: 6.005

3.  Stereoselective additions of thiyl radicals to terminal ynamides.

Authors:  Biplab Banerjee; Dmitry N Litvinov; Junghoon Kang; Jennifer D Bettale; Steven L Castle
Journal:  Org Lett       Date:  2010-06-04       Impact factor: 6.005

4.  Novel approach to pro-drugs of lactones: water soluble imidate and ortho-ester derivatives of a furanone-based COX-2 selective inhibitor.

Authors:  Steve F Poon; Nicholas Stock; Joseph E Payne; Angela R McGuire; Brian Stearns; Xiaoqing Yang; Weichao Chen; Benito Munoz; Nicholas D Smith
Journal:  Bioorg Med Chem Lett       Date:  2005-05-02       Impact factor: 2.823

5.  Access to 2,5-diamidopyrroles and 2,5-diamidofurans by au(i)-catalyzed double hydroamination or hydration of 1,3-diynes.

Authors:  Søren Kramer; Julie L H Madsen; Mario Rottländer; Troels Skrydstrup
Journal:  Org Lett       Date:  2010-06-18       Impact factor: 6.005

6.  Exploration of potential prodrugs of RWJ-445167, an oxyguanidine-based dual inhibitor of thrombin and factor Xa.

Authors:  Bruce E Maryanoff; David F McComsey; Michael J Costanzo; Stephen C Yabut; Tianbao Lu; Mark R Player; Edward C Giardino; Bruce P Damiano
Journal:  Chem Biol Drug Des       Date:  2006-07       Impact factor: 2.817

7.  Synthesis of aminocyclobutanes through ring expansion of N-vinyl-beta-lactams.

Authors:  Lawrence L W Cheung; Andrei K Yudin
Journal:  Org Lett       Date:  2009-03-19       Impact factor: 6.005

8.  A new entry of copper-catalyzed four-component reaction: facile access to alpha-aryl beta-hydroxy imidates.

Authors:  Eun Jeong Yoo; Sae Hume Park; Sang Hyup Lee; Sukbok Chang
Journal:  Org Lett       Date:  2009-03-05       Impact factor: 6.005

9.  Catalytic asymmetric rearrangement of allylic trichloroacetimidates. A practical method for preparing allylic amines and congeners of high enantiomeric purity.

Authors:  Carolyn E Anderson; Larry E Overman
Journal:  J Am Chem Soc       Date:  2003-10-15       Impact factor: 15.419

10.  Mechanistic studies on the Cu-catalyzed three-component reactions of sulfonyl azides, 1-alkynes and amines, alcohols, or water: dichotomy via a common pathway.

Authors:  Eun Jeong Yoo; Mårten Ahlquist; Imhyuck Bae; K Barry Sharpless; Valery V Fokin; Sukbok Chang
Journal:  J Org Chem       Date:  2008-06-17       Impact factor: 4.354
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  6 in total

1.  N-allyl-N-sulfonyl ynamides as synthetic precursors to amidines and vinylogous amidines. An unexpected N-to-C 1,3-sulfonyl shift in nitrile synthesis.

Authors:  Kyle A DeKorver; Whitney L Johnson; Yu Zhang; Richard P Hsung; Huifang Dai; Jun Deng; Andrew G Lohse; Yan-Shi Zhang
Journal:  J Org Chem       Date:  2011-05-24       Impact factor: 4.354

2.  Carbocyclization cascades of allyl ketenimines via aza-Claisen rearrangements of N-phosphoryl-N-allyl-ynamides.

Authors:  Kyle A DeKorver; Xiao-Na Wang; Mary C Walton; Richard P Hsung
Journal:  Org Lett       Date:  2012-03-13       Impact factor: 6.005

3.  Introducing a new class of N-phosphoryl ynamides via Cu(I)-catalyzed amidations of alkynyl bromides.

Authors:  Kyle A DeKorver; Mary C Walton; Troy D North; Richard P Hsung
Journal:  Org Lett       Date:  2011-08-17       Impact factor: 6.005

4.  Synthesis of cyclopentenimines from N-allyl ynamides via a tandem aza-Claisen rearrangement-carbocyclization sequence.

Authors:  Xiao-Na Wang; Gabrielle N Winston-McPherson; Mary C Walton; Yu Zhang; Richard P Hsung; Kyle A DeKorver
Journal:  J Org Chem       Date:  2013-06-10       Impact factor: 4.354

5.  Ynamides in ring forming transformations.

Authors:  Xiao-Na Wang; Hyun-Suk Yeom; Li-Chao Fang; Shuzhong He; Zhi-Xiong Ma; Brant L Kedrowski; Richard P Hsung
Journal:  Acc Chem Res       Date:  2013-10-28       Impact factor: 22.384

6.  Divergent C-H Insertion-Cyclization Cascades of N-Allyl Ynamides.

Authors:  Holly V Adcock; Elli Chatzopoulou; Paul W Davies
Journal:  Angew Chem Int Ed Engl       Date:  2015-10-30       Impact factor: 15.336
  6 in total

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