Literature DB >> 15548093

Utility of the iridium complex of the pybox ligand in regio- and enantioselective allylic substitution.

Hideto Miyabe1, Akira Matsumura, Katsuhiko Moriyama, Yoshiji Takemoto.   

Abstract

The viability of the iridium complex of pybox as chiral catalyst in allylic substitutions and the enantioselective synthesis of branched products was studied. Among several chiral ligands evaluated, the iridium complex of pybox having a phenyl group catalyzed the reaction with high activity to form the branched amines with good enantioselectivities when hydroxylamine, amine, and aniline were employed as a nucleophile. The allylic substitution with oximes proceeded smoothly to give the branched oxime ethers with good enantioselectivities. [reaction: see text]

Entities:  

Year:  2004        PMID: 15548093     DOI: 10.1021/ol047915t

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


  8 in total

1.  Primary tert- and sec-allylamines via palladium-catalyzed hydroamination and allylic substitution with hydrazine and hydroxylamine derivatives.

Authors:  Adam M Johns; Zhijian Liu; John F Hartwig
Journal:  Angew Chem Int Ed Engl       Date:  2007       Impact factor: 15.336

2.  Direct, iridium-catalyzed enantioselective and regioselective allylic etherification with aliphatic alcohols.

Authors:  Satoshi Ueno; John F Hartwig
Journal:  Angew Chem Int Ed Engl       Date:  2008       Impact factor: 15.336

3.  TPGS-750-M: a second-generation amphiphile for metal-catalyzed cross-couplings in water at room temperature.

Authors:  Bruce H Lipshutz; Subir Ghorai; Alexander R Abela; Ralph Moser; Takashi Nishikata; Christophe Duplais; Arkady Krasovskiy; Ricky D Gaston; Robert C Gadwood
Journal:  J Org Chem       Date:  2011-05-09       Impact factor: 4.354

4.  Iridium-catalyzed, regio- and enantioselective allylic substitution with aromatic and aliphatic sulfinates.

Authors:  Mitsuhiro Ueda; John F Hartwig
Journal:  Org Lett       Date:  2010-01-01       Impact factor: 6.005

5.  Regio- and enantioselective N-allylations of imidazole, benzimidazole, and purine heterocycles catalyzed by single-component metallacyclic iridium complexes.

Authors:  Levi M Stanley; John F Hartwig
Journal:  J Am Chem Soc       Date:  2009-07-01       Impact factor: 15.419

6.  Synthesis of Benzannulated Medium-ring Lactams via a Tandem Oxidative Dearomatization-Ring Expansion Reaction.

Authors:  Tezcan Guney; Todd A Wenderski; Matthew W Boudreau; Derek S Tan
Journal:  Chemistry       Date:  2018-08-02       Impact factor: 5.236

7.  Enantioselective construction of C-chiral allylic sulfilimines via the iridium-catalyzed allylic amination with S,S-diphenylsulfilimine: asymmetric synthesis of primary allylic amines.

Authors:  Rebecca L Grange; Elizabeth A Clizbe; Emma J Counsell; P Andrew Evans
Journal:  Chem Sci       Date:  2014-09-08       Impact factor: 9.825

8.  Tuning the Reactivity of Radical through a Triplet Diradical Cu(II) Intermediate in Radical Oxidative Cross-Coupling.

Authors:  Liangliang Zhou; Hong Yi; Lei Zhu; Xiaotian Qi; Hanpeng Jiang; Chao Liu; Yuqi Feng; Yu Lan; Aiwen Lei
Journal:  Sci Rep       Date:  2015-11-03       Impact factor: 4.379

  8 in total

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