Literature DB >> 26034330

Catalytic intramolecular decarbonylative coupling of 3-aminocyclobutenones and alkenes: a unique approach to [3.1.0] bicycles.

Xuan Zhou1, Imran Zafar1, Guangbin Dong1.   

Abstract

Here we describe a rhodium-catalyzed intramolecular decarbonylative coupling between 3-aminocyclobutenones and alkenes for synthesis of substituted [3.1.0] bicycles. This transformation represents a formal cyclopropanation reaction, in which the cyclobutenones serve as a one-carbon-unit synthon.

Entities:  

Keywords:  Cyclobutenone; Cyclopropanation; C–C cleavage; Decarbonylation; Rhodium catalysis

Year:  2015        PMID： 26034330      PMCID： PMC4448780          DOI： 10.1016/j.tet.2015.02.087

Source DB:  PubMed          Journal:  Tetrahedron        ISSN： 0040-4020            Impact factor:   2.457


  17 in total

1.  Highly enantioselective Rh-catalyzed carboacylation of olefins: efficient syntheses of chiral poly-fused rings.

Authors:  Tao Xu; Haye Min Ko; Nikolas A Savage; Guangbin Dong
Journal:  J Am Chem Soc       Date:  2012-11-28       Impact factor: 15.419

2.  Rhodium(I)-catalyzed decarbonylative spirocyclization through C-C bond cleavage of benzocyclobutenones: an efficient approach to functionalized spirocycles.

Authors:  Tao Xu; Nikolas A Savage; Guangbin Dong
Journal:  Angew Chem Int Ed Engl       Date:  2014-01-20       Impact factor: 15.336

3.  Cascade electrophilic iodocyclization: efficient preparation of 4-iodomethyl substituted tetrahydro-β-carbolines and formal synthesis of oxopropaline G.

Authors:  Hongjian Song; Yongxian Liu; Qingmin Wang
Journal:  Org Lett       Date:  2013-06-19       Impact factor: 6.005

4.  Coupling of sterically hindered trisubstituted olefins and benzocyclobutenones by C-C activation: total synthesis and structural revision of cycloinumakiol.

Authors:  Tao Xu; Guangbin Dong
Journal:  Angew Chem Int Ed Engl       Date:  2014-08-19       Impact factor: 15.336

5.  Cyclobutanes in catalysis.

Authors:  Tobias Seiser; Tanguy Saget; Duc N Tran; Nicolai Cramer
Journal:  Angew Chem Int Ed Engl       Date:  2011-07-26       Impact factor: 15.336

6.  Radical cyclization of 1,6-enynes using allylstannanes(1)

Authors: 
Journal:  J Org Chem       Date:  2000-11-17       Impact factor: 4.354

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.  Copper-catalyzed aerobic oxidative amidation of terminal alkynes: efficient synthesis of ynamides.

Authors:  Tetsuya Hamada; Xuan Ye; Shannon S Stahl
Journal:  J Am Chem Soc       Date:  2008-01-01       Impact factor: 15.419

9.  Divergent syntheses of fused β-naphthol and indene scaffolds by rhodium-catalyzed direct and decarbonylative alkyne-benzocyclobutenone couplings.

Authors:  Peng-Hao Chen; Tao Xu; Guangbin Dong
Journal:  Angew Chem Int Ed Engl       Date:  2014-01-21       Impact factor: 15.336

10.  Iron-catalyzed, hydrogen-mediated reductive cyclization of 1,6-enynes and diynes: evidence for bis(imino)pyridine ligand participation.

Authors:  Kevin T Sylvester; Paul J Chirik
Journal:  J Am Chem Soc       Date:  2009-07-01       Impact factor: 15.419
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  4 in total

1.  Kinetic Resolution via Rh-Catalyzed C-C Activation of Cyclobutanones at Room Temperature.

Authors:  Lin Deng; Yue Fu; Siu Yin Lee; Chengpeng Wang; Peng Liu; Guangbin Dong
Journal:  J Am Chem Soc       Date:  2019-10-02       Impact factor: 15.419

2.  Synthesis of Bridged Cyclopentane Derivatives by Catalytic Decarbonylative Cycloaddition of Cyclobutanones and Olefins.

Authors:  Xuan Zhou; Haye Min Ko; Guangbin Dong
Journal:  Angew Chem Int Ed Engl       Date:  2016-10-06       Impact factor: 15.336

Review 3.  Cyclobutenones and Benzocyclobutenones: Versatile Synthons in Organic Synthesis.

Authors:  Peng-Hao Chen; Guangbin Dong
Journal:  Chemistry       Date:  2016-09-13       Impact factor: 5.236

4.  Synthesis and applications of rhodacyclopentanones derived from C-C bond activation.

Authors:  Megan H Shaw; John F Bower
Journal:  Chem Commun (Camb)       Date:  2016-07-07       Impact factor: 6.222
  4 in total

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