Literature DB >> 19624104

Enamide-benzyne-[2 + 2] cycloaddition: stereoselective tandem [2 + 2]-pericyclic ring-opening-intramolecular N-tethered [4 + 2] cycloadditions.

John B Feltenberger1, Ryuji Hayashi, Yu Tang, Eric S C Babiash, Richard P Hsung.   

Abstract

Benzyne-[2 + 2] cycloadditions with enamides are described. This effort led to the development of a highly stereoselective tandem [2 + 2] cycloaddition-pericyclic ring-opening-intramolecular-N-tethered-[4 + 2] cycloaddition for rapid assembly of nitrogen heterocycles.

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Year:  2009        PMID： 19624104      PMCID： PMC2822464          DOI： 10.1021/ol901434g

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


  44 in total

1.  Stereoselective synthesis of isomeric functionalized 1,3-dienes from cyclobutenones.

Authors:  M Murakami; Y Miyamoto; Y Ito
Journal:  J Am Chem Soc       Date:  2001-07-04       Impact factor: 15.419

2.  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

3.  A stereoselective intramolecular halo-etherification of chiral enamides in the synthesis of halogenated cyclic ethers.

Authors:  Changhong Ko; Richard P Hsung; Ziyad F Al-Rashid; John B Feltenberger; Ting Lu; Jin-Haek Yang; Yonggang Wei; Craig A Zificsak
Journal:  Org Lett       Date:  2007-10-02       Impact factor: 6.005

Review 4.  Copper-mediated coupling reactions and their applications in natural products and designed biomolecules synthesis.

Authors:  Gwilherm Evano; Nicolas Blanchard; Mathieu Toumi
Journal:  Chem Rev       Date:  2008-08       Impact factor: 60.622

5.  Origins of inward torquoselectivity by silyl groups and other sigma-acceptors in electrocyclic reactions of cyclobutenes.

Authors:  Patrick S Lee; Xiyun Zhang; K N Houk
Journal:  J Am Chem Soc       Date:  2003-04-30       Impact factor: 15.419

6.  The direct acyl-alkylation of arynes.

Authors:  Uttam K Tambar; Brian M Stoltz
Journal:  J Am Chem Soc       Date:  2005-04-20       Impact factor: 15.419

7.  A convergent and enantioselective synthesis of (+)-amurensinine via selective C-H and C-C bond insertion reactions.

Authors:  Uttam K Tambar; David C Ebner; Brian M Stoltz
Journal:  J Am Chem Soc       Date:  2006-09-13       Impact factor: 15.419

8.  Copper-catalyzed coupling of amides and carbamates with vinyl halides.

Authors:  Lei Jiang; Gabriel E Job; Artis Klapars; Stephen L Buchwald
Journal:  Org Lett       Date:  2003-10-02       Impact factor: 6.005

9.  Copper-catalyzed alkyne-aryne and alkyne-alkene-aryne coupling reactions.

Authors:  Chunsong Xie; Leifang Liu; Yuhong Zhang; Peixin Xu
Journal:  Org Lett       Date:  2008-05-17       Impact factor: 6.005

10.  CuI/N,N-dimethylglycine-catalyzed coupling of vinyl halides with amides or carbamates.

Authors:  Xianhua Pan; Qian Cai; Dawei Ma
Journal:  Org Lett       Date:  2004-05-27       Impact factor: 6.005
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  10 in total

1.  A highly regio- and stereoselective synthesis of α-fluorinated imides via fluorination of chiral enamides.

Authors:  Yan-Shuang Xu; Yu Tang; He-Jing Feng; Ji-Tian Liu; Richard P Hsung
Journal:  Org Lett       Date:  2015-01-12       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.  An oxidation of benzyl methyl ethers with nbs that selectively affords either aromatic aldehydes or aromatic methyl esters.

Authors:  Abdelrahman S Mayhoub; Arindam Talukdar; Mark Cushman
Journal:  J Org Chem       Date:  2010-05-21       Impact factor: 4.354

4.  Cycloaddition of Arynes and Cyclic Enol Ethers as a Platform for Access to Stereochemically Defined 1,2-Disubstituted Benzocyclobutenes.

Authors:  Vijayendar R Yedulla; Padmanava Pradhan; Lijia Yang; Mahesh K Lakshman
Journal:  European J Org Chem       Date:  2014-12-22

5.  Synthesis of 2H-indazoles by the [3 + 2] dipolar cycloaddition of sydnones with arynes.

Authors:  Yuesi Fang; Chunrui Wu; Richard C Larock; Feng Shi
Journal:  J Org Chem       Date:  2011-10-12       Impact factor: 4.354

6.  Synthesis of dihydrobenzisoxazoles by the [3 + 2] cycloaddition of arynes and oxaziridines.

Authors:  Arif Kivrak; Richard C Larock
Journal:  J Org Chem       Date:  2010-11-05       Impact factor: 4.354

7.  Total syntheses of chelidonine and norchelidonine via an enamide-benzyne-[2 + 2] cycloaddition cascade.

Authors:  Zhi-Xiong Ma; John B Feltenberger; Richard P Hsung
Journal:  Org Lett       Date:  2012-05-10       Impact factor: 6.005

8.  Direct access to functionalized azepanes by cross-coupling with α-halo eneformamides.

Authors:  Timothy K Beng; Sidney M Wilkerson-Hill; Richmond Sarpong
Journal:  Org Lett       Date:  2014-01-23       Impact factor: 6.005

9.  Three-component coupling reactions of arynes for the synthesis of benzofurans and coumarins.

Authors:  Eito Yoshioka; Shigeru Kohtani; Hideto Miyabe
Journal:  Molecules       Date:  2014-01-13       Impact factor: 4.411

10.  Direct Synthesis of Enamides via Electrophilic Activation of Amides.

Authors:  Philipp Spieß; Martin Berger; Daniel Kaiser; Nuno Maulide
Journal:  J Am Chem Soc       Date:  2021-07-07       Impact factor: 15.419
  10 in total

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