Literature DB >> 17929826

Asymmetric 1,3-dipolar cycloadditions of nitrones and methacrolein catalyzed by chiral bis-titanium lewis acid: a dramatic effect of N-substituent on nitrone.

Takuya Hashimoto1, Masato Omote, Taichi Kano, Keiji Maruoka.   

Abstract

Highly stereoselective 1,3-dipolar cycloadditions of methacrolein and nitrones could be realized by the use of bis-titanium chiral Lewis acid catalyst. Key to the success is the introduction of bulky N-substituent on nitrone to attenuate the undesired Lewis acid-nitrone complexation.

Entities:  

Year:  2007        PMID: 17929826     DOI: 10.1021/ol702123n

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


  4 in total

1.  Asymmeric formal [3 + 3]-cycloaddition reactions of nitrones with electrophilic vinylcarbene intermediates.

Authors:  Xiaochen Wang; Xinfang Xu; Peter Y Zavalij; Michael P Doyle
Journal:  J Am Chem Soc       Date:  2011-09-27       Impact factor: 15.419

2.  Solvent enhancement of reaction selectivity: a unique property of cationic chiral dirhodium carboxamidates.

Authors:  Xiaochen Wang; Carolin Weigl; Michael P Doyle
Journal:  J Am Chem Soc       Date:  2011-05-27       Impact factor: 15.419

3.  Asymmetric bisboranes as bidentate catalysts for carbonyl substrates.

Authors:  Andrew A Rodriguez; Carrie Zhao; Kenneth J Shea
Journal:  Org Lett       Date:  2009-02-05       Impact factor: 6.005

4.  Catalytic Asymmetric Formal [3+2] Cycloaddition of Azoalkenes with 3-Vinylindoles: Synthesis of 2,3-Dihydropyrroles.

Authors:  Guang-Jian Mei; Wenrui Zheng; Théo P Gonçalves; Xiwen Tang; Kuo-Wei Huang; Yixin Lu
Journal:  iScience       Date:  2020-01-31
  4 in total

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