Literature DB >> 10956537

On the regioselectivity of the Ru-catalyzed intramolecular [5 + 2] cycloaddition.

B M Trost1, H C Shen.   

Abstract

The influence of substituents on which cyclopropyl bond cleaves in the cycloisomerization of cyclopropylenynes catalyzed by CpRu(N&tbd1;CCH(3))(3)(+)PF(6)(-) is compared to the corresponding Rh-catalyzed reaction. With the trans cyclopropyl substrates, the bond energy of the cleaving bond appears to be an important factor. With cis cyclopropyl substrates, steric effects appear to dominate.

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Year:  2000        PMID： 10956537     DOI： 10.1021/ol0061945

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


  7 in total

1.  Rhodium-catalyzed ring expansion of cyclopropanes to seven-membered rings by 1,5 C-C bond migration.

Authors:  Xiaoxun Li; Min Zhang; Dongxu Shu; Patrick J Robichaux; Suyu Huang; Weiping Tang
Journal:  Angew Chem Int Ed Engl       Date:  2011-09-09       Impact factor: 15.336

2.  Synthesis of highly functionalized cyclohexenone rings: rhodium-catalyzed 1,3-acyloxy migration and subsequent [5+1] cycloaddition.

Authors:  Dongxu Shu; Xiaoxun Li; Min Zhang; Patrick J Robichaux; Weiping Tang
Journal:  Angew Chem Int Ed Engl       Date:  2010-12-29       Impact factor: 15.336

3.  Total synthesis of (-)-pseudolaric acid B.

Authors:  Barry M Trost; Jerome Waser; Arndt Meyer
Journal:  J Am Chem Soc       Date:  2008-12-03       Impact factor: 15.419

4.  Rhodium-catalyzed carbonylation of cyclopropyl substituted propargyl esters: a tandem 1,3-acyloxy migration [5 + 1] cycloaddition.

Authors:  Dongxu Shu; Xiaoxun Li; Min Zhang; Patrick J Robichaux; Ilia A Guzei; Weiping Tang
Journal:  J Org Chem       Date:  2012-07-25       Impact factor: 4.354

Review 5.  Ruthenium-Catalyzed Cycloadditions to Form Five-, Six-, and Seven-Membered Rings.

Authors:  Rosalie S Doerksen; Tomáš Hodík; Guanyu Hu; Nancy O Huynh; William G Shuler; Michael J Krische
Journal:  Chem Rev       Date:  2021-02-12       Impact factor: 60.622

6.  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

7.  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
  7 in total

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