Literature DB >> 24446318

Atom-economic, regiodivergent, and stereoselective coupling of imidazole derivatives with terminal allenes.

Kun Xu1, Niels Thieme, Bernhard Breit.   

Abstract

New Rh- and Pd-catalyzed regiodivergent and stereoselective intermolecular coupling reactions of imidazole derivatives with mono-substituted allenes are herein reported. Using a Rh(I)/Josiphos system, perfect regioselectivities and high enantiomeric excess were obtained, while a Pd(II)/dppf system gave linear products with high regioselectivities and high E/Z selectivities. This method permits the atom economic synthesis of valuable branched and linear allylic imidazole derivatives.
Copyright © 2014 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  allenes; allylic compounds; asymmetric catalysis; heterocycles; rhodium

Mesh:

Substances:

Year:  2014        PMID: 24446318     DOI: 10.1002/anie.201309126

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


  7 in total

1.  Rhodium-Catalyzed Enantioselective Hydroamination of Alkynes with Indolines.

Authors:  Qing-An Chen; Zhiwei Chen; Vy M Dong
Journal:  J Am Chem Soc       Date:  2015-06-29       Impact factor: 15.419

2.  Preparation of Chiral Allenes through Pd-Catalyzed Intermolecular Hydroamination of Conjugated Enynes: Enantioselective Synthesis Enabled by Catalyst Design.

Authors:  Nathan J Adamson; Haleh Jeddi; Steven J Malcolmson
Journal:  J Am Chem Soc       Date:  2019-05-15       Impact factor: 15.419

3.  Ligand-Controlled Regioselective Copper-Catalyzed Trifluoromethylation To Generate (Trifluoromethyl)allenes.

Authors:  Brett R Ambler; Santosh Peddi; Ryan A Altman
Journal:  Org Lett       Date:  2015-04-24       Impact factor: 6.005

4.  Enantioselective C2-Allylation of Benzimidazoles Using 1,3-Diene Pronucleophiles.

Authors:  James Levi Knippel; Yuxuan Ye; Stephen L Buchwald
Journal:  Org Lett       Date:  2021-03-01       Impact factor: 6.005

5.  Regiocontrol in catalytic reductive couplings through alterations of silane rate dependence.

Authors:  Evan P Jackson; John Montgomery
Journal:  J Am Chem Soc       Date:  2015-01-05       Impact factor: 15.419

6.  Non-bonding 1,5-S···O interactions govern chemo- and enantioselectivity in isothiourea-catalyzed annulations of benzazoles.

Authors:  Emily R T Robinson; Daniel M Walden; Charlene Fallan; Mark D Greenhalgh; Paul Ha-Yeon Cheong; Andrew D Smith
Journal:  Chem Sci       Date:  2016-07-04       Impact factor: 9.825

7.  Asymmetric synthesis of allylic amines via hydroamination of allenes with benzophenone imine.

Authors:  Kun Xu; Yu-Hsuan Wang; Vahid Khakyzadeh; Bernhard Breit
Journal:  Chem Sci       Date:  2016-02-09       Impact factor: 9.825

  7 in total

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