Literature DB >> 25533025

Experimental and computational study of the catalytic asymmetric 4π-electrocyclization of N-heterocycles.

Sadiya Raja1, Masaki Nakajima, Magnus Rueping.   

Abstract

The first asymmetric metal-catalyzed Nazarov cyclization of N-heterocycles has been developed. The use of a chiral catalyst allows the enantioselective electrocyclization of N-heterocycles under mild conditions and the corresponding products are obtained in good yields with excellent enantio- and diastereoselectivity. The reaction mechanism and the absolute configuration of the obtained products are explained by means of computational studies.
© 2015 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  Lewis acid catalysis; Nazarov reaction; electrocyclization; indole alkaloids

Mesh:

Substances:

Year:  2014        PMID: 25533025     DOI: 10.1002/anie.201408020

Source DB:  PubMed          Journal:  Angew Chem Int Ed Engl        ISSN: 1433-7851            Impact factor:   15.336


  6 in total

Review 1.  Recent metal-catalysed approaches for the synthesis of cyclopenta[b]indoles.

Authors:  Thavaraj Vivekanand; Bishnupada Satpathi; Siddheshwar K Bankar; S S V Ramasastry
Journal:  RSC Adv       Date:  2018-05-22       Impact factor: 4.036

2.  Enantioselective Nazarov cyclization of indole enones cooperatively catalyzed by Lewis acids and chiral Brønsted acids.

Authors:  Guo-Peng Wang; Meng-Qing Chen; Shou-Fei Zhu; Qi-Lin Zhou
Journal:  Chem Sci       Date:  2017-08-29       Impact factor: 9.825

3.  Asymmetric Gold(I)-Catalyzed Tandem Hydroarylation-Nazarov Cyclization: Enantioselective Access to Cyclopentenones.

Authors:  Marta Solas; Samuel Suárez-Pantiga; Roberto Sanz
Journal:  Angew Chem Int Ed Engl       Date:  2022-07-18       Impact factor: 16.823

4.  Chiral cis-iron(ii) complexes with metal- and ligand-centered chirality for highly regio- and enantioselective alkylation of N-heteroaromatics.

Authors:  Jinhu Wei; Bei Cao; Chun-Wai Tse; Xiao-Yong Chang; Cong-Ying Zhou; Chi-Ming Che
Journal:  Chem Sci       Date:  2019-11-25       Impact factor: 9.825

5.  Enantioselective Synthesis of Chiral Cyclopent-2-enones by Nickel-Catalyzed Desymmetrization of Malonate Esters.

Authors:  Somnath Narayan Karad; Heena Panchal; Christopher Clarke; William Lewis; Hon Wai Lam
Journal:  Angew Chem Int Ed Engl       Date:  2018-06-19       Impact factor: 15.336

6.  Bis-Cyclometalated Indazole and Benzimidazole Chiral-at-Iridium Complexes: Synthesis and Asymmetric Catalysis.

Authors:  Sebastian Brunen; Yvonne Grell; Philipp S Steinlandt; Klaus Harms; Eric Meggers
Journal:  Molecules       Date:  2021-03-24       Impact factor: 4.411

  6 in total

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