Literature DB >> 17880234

Dipole-LUMO/dipolarophile-HOMO controlled asymmetric cycloadditions of carbonyl ylides catalyzed by chiral Lewis acids.

Hiroyuki Suga1, Daisuke Ishimoto, Satoshi Higuchi, Motoo Ohtsuka, Tadashi Arikawa, Teruko Tsuchida, Akikazu Kakehi, Toshihide Baba.   

Abstract

We have found the first successful example of reverse-electron-demand dipole-LUMO/dipolarophile-HOMO controlled cycloaddition reactions between carbonyl ylides, which were generated from o-methoxycarbonyl-alpha-diazoacetophenone and their acyl derivatives as precursors, and vinyl ether derivatives with high levels of asymmetric induction (97-77% ee) using chiral 2,6-(oxazolinyl)pyridine-Eu(III) or binaphthyldiimine-Ni(II) complexes as chiral Lewis acid catalysts.

Entities:  

Year:  2007        PMID： 17880234     DOI： 10.1021/ol701936b

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


  3 in total

1.  Enantioselective Photocatalytic [3 + 2] Cycloadditions of Aryl Cyclopropyl Ketones.

Authors:  Adrian G Amador; Evan M Sherbrook; Tehshik P Yoon
Journal:  J Am Chem Soc       Date:  2016-03-29       Impact factor: 15.419

2.  Synthesis, crystal structure and Hirshfeld surface analysis of dimethyl 3-(3-bromo-phen-yl)-6-methyl-7-oxo-3,5,6,7-tetra-hydro-pyrazolo-[1,2-a]pyrazole-1,2-di-carboxyl-ate.

Authors:  Rahhal El Ajlaoui; Yassine Hakmaoui; El Mostapha Rakib; El Mostafa Ketatni; Mohamed Saadi; Lahcen El Ammari
Journal:  Acta Crystallogr E Crystallogr Commun       Date:  2022-01-07

3.  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
  3 in total

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