Literature DB >> 20192198

Reaction of alpha-ene-vinylcyclopropanes: type II intramolecular [5+2] cycloaddition or [3+2] cycloaddition?

Qian Li1, Guo-Jie Jiang, Lei Jiao, Zhi-Xiang Yu.   

Abstract

Exposure of alpha-ene-VCPs to catalytic [Rh(dppm)]SbF(6) led to the discovery of a novel Rh(I)-catalyzed [3+2] reaction, which was shown to be efficient for the construction of 5/6- and 5/7-bicyclic compounds rather than the anticipated type II [5+2] products.

Entities:  

Year:  2010        PMID： 20192198     DOI： 10.1021/ol100237h

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


  10 in total

1.  Rhodium-catalyzed intra- and intermolecular [5 + 2] cycloaddition of 3-acyloxy-1,4-enyne and alkyne with concomitant 1,2-acyloxy migration.

Authors:  Xing-Zhong Shu; Xiaoxun Li; Dongxu Shu; Suyu Huang; Casi M Schienebeck; Xin Zhou; Patrick J Robichaux; Weiping Tang
Journal:  J Am Chem Soc       Date:  2012-03-12       Impact factor: 15.419

2.  Transfer of chirality in the rhodium-catalyzed intramolecular [5+2] cycloaddition of 3-acyloxy-1,4-enynes (ACEs) and alkynes: synthesis of enantioenriched bicyclo[5.3.0]decatrienes.

Authors:  Xing-Zhong Shu; Casi M Schienebeck; Wangze Song; Ilia A Guzei; Weiping Tang
Journal:  Angew Chem Int Ed Engl       Date:  2013-10-21       Impact factor: 15.336

3.  Radical [3 + 2]-annulation of divinylcyclopropanes: rapid synthesis of complex meloscine analogs.

Authors:  Hanmo Zhang; Kyu Ok Jeon; E Ben Hay; Steven J Geib; Dennis P Curran; Matthew G LaPorte
Journal:  Org Lett       Date:  2013-12-06       Impact factor: 6.005

4.  [3+2] cycloadditions of aryl cyclopropyl ketones by visible light photocatalysis.

Authors:  Zhan Lu; Meihua Shen; Tehshik P Yoon
Journal:  J Am Chem Soc       Date:  2011-01-07       Impact factor: 15.419

5.  Palladium-catalyzed diastereo- and enantioselective formal [3 + 2]-cycloadditions of substituted vinylcyclopropanes.

Authors:  Barry M Trost; Patrick J Morris; Simon J Sprague
Journal:  J Am Chem Soc       Date:  2012-10-10       Impact factor: 15.419

6.  "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

7.  Rh-catalyzed (5+2) cycloadditions of 3-acyloxy-1,4-enynes and alkynes: computational study of mechanism, reactivity, and regioselectivity.

Authors:  Xiufang Xu; Peng Liu; Xing-zhong Shu; Weiping Tang; K N Houk
Journal:  J Am Chem Soc       Date:  2013-06-14       Impact factor: 15.419

8.  3-Acyloxy-1,4-enyne: a New Five-carbon Synthon for Rhodium-Catalyzed (5+2) Cycloadditions.

Authors:  Casi M Schienebeck; Xiaoxun Li; Xing-Zhong Shu; Weiping Tang
Journal:  Pure Appl Chem       Date:  2014-03-01       Impact factor: 2.453

9.  An umpolung reaction of α-iminothioesters possessing a cyclopropyl group.

Authors:  Makoto Shimizu; Takayoshi Morimoto; Yusuke Yanagi; Isao Mizota; Yusong Zhu
Journal:  RSC Adv       Date:  2020-03-10       Impact factor: 4.036

10.  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
  10 in total

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