Literature DB >> 21250688

Rh(I)-catalyzed formal [5 + 1]/[2 + 2 + 1] cycloaddition of 1-yne-vinylcyclopropanes and two CO units: one-step construction of multifunctional angular tricyclic 5/5/6 compounds.

Mu Lin1, Feng Li, Lei Jiao, Zhi-Xiang Yu.   

Abstract

A novel Rh(I)-catalyzed formal [5 + 1]/[2 + 2 + 1] cycloaddition of 1-yne-vinylcyclopropanes and two CO units for the construction of multifunctional angular tricyclic 5/5/6 skeletons with one or two adjacent bridgehead quaternary all-carbon stereocenters in one step has been developed. Preliminary density functional theory calculations have been carried out to investigate the reaction mechanism and the substituent effects.

Entities:  

Year:  2011        PMID： 21250688     DOI： 10.1021/ja110039h

Source DB:  PubMed          Journal:  J Am Chem Soc        ISSN： 0002-7863            Impact factor:   15.419


  8 in total

1.  Mechanism and Reactivity of Rh-Catalyzed Intermolecular [5+1] Cycloaddition of 3-Acyloxy-1,4-Enyne (ACE) and CO: A Computational Study.

Authors:  Xiao-Na Ke; Casi M Schienebeck; Chen-Chen Zhou; Xiufang Xu; Weiping Tang
Journal:  Chin Chem Lett       Date:  2015-03-27       Impact factor: 6.779

2.  "Cut and Sew" Transformations via Transition-Metal-Catalyzed Carbon-Carbon Bond Activation.

Authors:  Peng-Hao Chen; Brent A Billett; Tatsuhiro Tsukamoto; Guangbin Dong
Journal:  ACS Catal       Date:  2017-01-06       Impact factor: 13.084

3.  Rhodium-catalyzed tandem annulation and (5 + 1) cycloaddition: 3-hydroxy-1,4-enyne as the 5-carbon component.

Authors:  Xiaoxun Li; Wangze Song; Weiping Tang
Journal:  J Am Chem Soc       Date:  2013-10-31       Impact factor: 15.419

4.  Catalytic [5 + 1]-Cycloadditions of Vinylcyclopropanes and Vinylidenes.

Authors:  Conner M Farley; Kohei Sasakura; You-Yun Zhou; Vibha V Kanale; Christopher Uyeda
Journal:  J Am Chem Soc       Date:  2020-02-27       Impact factor: 15.419

5.  Reactivity and chemoselectivity of allenes in Rh(I)-catalyzed intermolecular (5 + 2) cycloadditions with vinylcyclopropanes: allene-mediated rhodacycle formation can poison Rh(I)-catalyzed cycloadditions.

Authors:  Xin Hong; Matthew C Stevens; Peng Liu; Paul A Wender; K N Houk
Journal:  J Am Chem Soc       Date:  2014-11-24       Impact factor: 15.419

6.  The origin of the ligand-controlled regioselectivity in Rh-catalyzed [(2 + 2) + 2] carbocyclizations: steric vs. stereoelectronic effects.

Authors:  Douglas W Crandell; Shivnath Mazumder; P Andrew Evans; Mu-Hyun Baik
Journal:  Chem Sci       Date:  2015-08-25       Impact factor: 9.825

7.  Constructing chiral bicyclo[3.2.1]octanes via palladium-catalyzed asymmetric tandem Heck/carbonylation desymmetrization of cyclopentenes.

Authors:  Zhenbo Yuan; Yuye Zeng; Ziwen Feng; Zhe Guan; Aijun Lin; Hequan Yao
Journal:  Nat Commun       Date:  2020-05-21       Impact factor: 14.919

8.  Transition Metal-Catalyzed Selective Carbon-Carbon Bond Cleavage of Vinylcyclopropanes in Cycloaddition Reactions.

Authors:  Jianhua Wang; Stephanie A Blaszczyk; Xiaoxun Li; Weiping Tang
Journal:  Chem Rev       Date:  2020-08-05       Impact factor: 72.087
  8 in total

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