Literature DB >> 35274165

Enantioselective Allylic C-H Bond Oxidation of Olefins Using Copper Complexes of Chiral Oxazoline Based Ligands.

Saadi Samadi1, Hamid Arvinnezhad2, Saber Nazari2, Shiva Majidian2.   

Abstract

This review article discusses historical and contemporary research studies of asymmetric allylic oxidation of olefins using homogeneous and heterogeneous copper complexes of various kinds of oxazoline-based ligands, until the end of 2021. It is revealed that this strategy is a powerful method to form a new stereogenic center bearing an oxygen substituent adjacent to an unchanged C=C bond. Enantioselectivities as well as chemical yields, and also the reactivity, are strongly dependent on the type of substrate, oxidant, the copper salt and its oxidation state, ligand structure, temperature, nature of the solvent, and additives such as phenylhydrazine and porous materials.
© 2022. The Author(s), under exclusive licence to Springer Nature Switzerland AG.

Entities:  

Keywords:  Allylic ester; Asymmetric allylic C–H bond oxidation; Copper complexes of chiral oxazoline ligands; Olefin; Perester

Mesh:

Substances:

Year:  2022        PMID: 35274165     DOI: 10.1007/s41061-022-00375-9

Source DB:  PubMed          Journal:  Top Curr Chem (Cham)        ISSN: 2364-8961


  19 in total

1.  The synthesis of oxazolines using the vilsmeier reagent

Authors: 
Journal:  J Org Chem       Date:  2000-12-29       Impact factor: 4.354

2.  Novel metal complexes containing a chiral trinitrogen isoindoline-based pincer ligand: in situ synthesis and structural characterization.

Authors:  Jessica L Cryder; Andrew J Killgore; Curtis Moore; James A Golen; Arnold L Rheingold; Christopher J A Daley
Journal:  Dalton Trans       Date:  2010-10-06       Impact factor: 4.390

3.  Update 1 of: C2-symmetric chiral bis(oxazoline) ligands in asymmetric catalysis.

Authors:  Giovanni Desimoni; Giuseppe Faita; Karl Anker Jørgensen
Journal:  Chem Rev       Date:  2011-11-09       Impact factor: 60.622

Review 4.  C(2)-symmetric chiral bis(oxazoline) ligands in asymmetric catalysis.

Authors:  Giovanni Desimoni; Giuseppe Faita; Karl Anker Jørgensen
Journal:  Chem Rev       Date:  2006-09       Impact factor: 60.622

5.  Enantioselective Three-Step Synthesis of Homo-β-proline: A Donor-Acceptor Cyclopropane as Key Intermediate.

Authors:  Ludwig K A Pilsl; Thomas Ertl; Oliver Reiser
Journal:  Org Lett       Date:  2017-05-09       Impact factor: 6.005

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Authors:  Anja Gissibl; M G Finn; Oliver Reiser
Journal:  Org Lett       Date:  2005-06-09       Impact factor: 6.005

7.  Studies on enantioselective allylic oxidation of olefins using peresters catalyzed by Cu(I)-complexes of chiral pybox ligands.

Authors:  Sandeep K Ginotra; Vinod K Singh
Journal:  Org Biomol Chem       Date:  2006-10-24       Impact factor: 3.876

8.  Development of bifunctional aza-bis(oxazoline) copper catalysts for enantioselective Henry reaction.

Authors:  Kai Lang; Jongwoo Park; Sukwon Hong
Journal:  J Org Chem       Date:  2010-10-01       Impact factor: 4.354

9.  The role of binding constants in the efficiency of chiral catalysts immobilized by electrostatic interactions: the case of azabis(oxazoline)-copper complexes.

Authors:  José M Fraile; José I García; Clara I Herrerías; José A Mayoral; Oliver Reiser; Antonio Socuéllamos; Heiko Werner
Journal:  Chemistry       Date:  2004-06-21       Impact factor: 5.236

10.  Theoretical insights into enantioselective catalysis: the mechanism of the Kharasch-Sosnovsky reaction.

Authors:  José Antonio Mayoral; Sergio Rodríguez-Rodríguez; Luis Salvatella
Journal:  Chemistry       Date:  2008       Impact factor: 5.236

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  1 in total

1.  Preparation and DFT studies of chiral Cu (I)-complexes of biphenyl bisoxazolines and their application in enantioselective Kharasch-Sosnovsky reaction.

Authors:  Saadi Samadi; Hamid Arvinnezhad; Sirwan Mansoori; Hadi Parsa
Journal:  Sci Rep       Date:  2022-09-03       Impact factor: 4.996

  1 in total

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