Literature DB >> 20690601

Copper-catalyzed Ficini [2 + 2] cycloaddition of ynamides.

Hongyan Li1, Richard P Hsung, Kyle A DeKorver, Yonggang Wei.   

Abstract

The Ficini [2 + 2] cycloaddition using N-sulfonyl-substituted ynamides is described, featuring the utility of CuCl(2) and AgSbF(6) as catalysts. This work represents the first successful example of ynamides participating in a thermal [2 + 2] cycloaddition with enones.

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Year:  2010        PMID： 20690601      PMCID： PMC2962578          DOI： 10.1021/ol101418d

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


  22 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.  Diastereoselective gold-catalyzed cycloisomerizations of ene-ynamides.

Authors:  Sylvain Couty; Christophe Meyer; Janine Cossy
Journal:  Angew Chem Int Ed Engl       Date:  2006-10-13       Impact factor: 15.336

4.  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

5.  Ruthenium-catalyzed [2 + 2] cycloadditions of ynamides.

Authors:  Nicole Riddell; Karine Villeneuve; William Tam
Journal:  Org Lett       Date:  2005-08-18       Impact factor: 6.005

6.  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

7.  [2+2] Cycloaddition of ketenes with ynamides. A general method for the synthesis of 3-aminocyclobutenone derivatives.

Authors:  Amanda L Kohnen; Xiao Yin Mak; Tin Yiu Lam; Joshua R Dunetz; Rick L Danheiser
Journal:  Tetrahedron       Date:  2006-04-17       Impact factor: 2.457

8.  A Stereoselective Intramolecular Cyclopropanation via a De Novo Class of Push-Pull Carbenes Derived from DMDO-Epoxidations of Chiral Ynamides.

Authors:  Hongyan Li; Jennifer E Antoline; Jin-Haek Yang; Ziyad F Al-Rashid; Richard P Hsung
Journal:  New J Chem       Date:  2010-01-01       Impact factor: 3.591

9.  A rhodium(I)-catalyzed demethylation-cyclization of o-anisole-substituted ynamides in the synthesis of chiral 2-amido benzofurans.

Authors:  Jossian Oppenheimer; Whitney L Johnson; Michael R Tracey; Richard P Hsung; Pei-Yuan Yao; Renhe Liu; Kang Zhao
Journal:  Org Lett       Date:  2007-05-10       Impact factor: 6.005

10.  Sonogashira cross-couplings of ynamides. Syntheses of urethane- and sulfonamide-terminated conjugated phenylacetylenic systems.

Authors:  Michael R Tracey; Yanshi Zhang; Michael O Frederick; Jason A Mulder; Richard P Hsung
Journal:  Org Lett       Date:  2004-06-24       Impact factor: 6.005
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  6 in total

1.  Batch and flow photochemical benzannulations based on the reaction of ynamides and diazo ketones. Application to the synthesis of polycyclic aromatic and heteroaromatic compounds.

Authors:  Thomas P Willumstad; Olesya Haze; Xiao Yin Mak; Tin Yiu Lam; Yu-Pu Wang; Rick L Danheiser
Journal:  J Org Chem       Date:  2013-10-28       Impact factor: 4.354

2.  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

3.  AlCl₃-Catalyzed Ring Expansion Cascades of Bicyclic Cyclobutenamides Involving Highly Strained Cis,Trans-Cycloheptadienone Intermediates.

Authors:  Xiao-Na Wang; Elizabeth H Krenske; Ryne C Johnston; K N Houk; Richard P Hsung
Journal:  J Am Chem Soc       Date:  2015-04-20       Impact factor: 15.419

4.  A Silver(I)-Catalyzed Intramolecular Ficini's [2 + 2] Cycloaddition Employing Ynamides.

Authors:  Xiao-Na Wang; Zhi-Xiong Ma; Jun Deng; Richard P Hsung
Journal:  Tetrahedron Lett       Date:  2015-06-03       Impact factor: 2.415

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.  Torquoselective ring opening of fused cyclobutenamides: evidence for a cis,trans-cyclooctadienone intermediate.

Authors:  Xiao-Na Wang; Elizabeth H Krenske; Ryne C Johnston; K N Houk; Richard P Hsung
Journal:  J Am Chem Soc       Date:  2014-07-03       Impact factor: 15.419
  6 in total

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