Literature DB >> 23559155

Amide-controlled highly selective catalytic borylcupration of allenes.

Weiming Yuan1, Xue Zhang, Yihua Yu, Shengming Ma.   

Abstract

A novel copper-catalyzed, highly regio- and stereoselective borylcupration of substituted 2,3-allenamides with bis(pinacolato)diboron producing Z-β-borylated β,γ-unsaturated enoamides has been demonstrated. Due to the unique effect of the amide-group, perfect regio- and stereoselectivity and good to excellent yields have been achieved, which were rationalized by a DFT study.
Copyright © 2013 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Year:  2013        PMID: 23559155     DOI: 10.1002/chem.201202835

Source DB:  PubMed          Journal:  Chemistry        ISSN: 0947-6539            Impact factor:   5.236


  8 in total

1.  Enantio- and diastereoselective synthesis of syn-β-hydroxy-α-vinyl carboxylic esters via reductive aldol reactions of ethyl allenecarboxylate with 10-TMS-9-Borabicyclo[3.3.2]decane and DFT analysis of the hydroboration pathway.

Authors:  Jeremy Kister; Daniel H Ess; William R Roush
Journal:  Org Lett       Date:  2013-10-18       Impact factor: 6.005

2.  Palladium-Catalyzed Oxidative Carbocyclization-Borylation of Enallenes to Cyclobutenes.

Authors:  Youai Qiu; Bin Yang; Can Zhu; Jan-E Bäckvall
Journal:  Angew Chem Int Ed Engl       Date:  2016-04-18       Impact factor: 15.336

3.  Enantioselective Generation of Adjacent Stereocenters in a Copper-Catalyzed Three-Component Coupling of Imines, Allenes, and Diboranes.

Authors:  Kay Yeung; Rebecca E Ruscoe; James Rae; Alexander P Pulis; David J Procter
Journal:  Angew Chem Int Ed Engl       Date:  2016-08-19       Impact factor: 15.336

Review 4.  Enantioselective copper catalysed, direct functionalisation of allenes via allyl copper intermediates.

Authors:  Alexander P Pulis; Kay Yeung; David J Procter
Journal:  Chem Sci       Date:  2017-06-08       Impact factor: 9.825

5.  Ru-catalyzed isomerization of ω-alkenylboronates towards stereoselective synthesis of vinylboronates with subsequent in situ functionalization.

Authors:  Guo-Ming Ho; Lucas Segura; Ilan Marek
Journal:  Chem Sci       Date:  2020-05-26       Impact factor: 9.825

6.  Catalytic Borylative Opening of Propargyl Cyclopropane, Epoxide, Aziridine, and Oxetane Substrates: Ligand Controlled Synthesis of Allenyl Boronates and Alkenyl Diboronates.

Authors:  Jian Zhao; Kálmán J Szabó
Journal:  Angew Chem Int Ed Engl       Date:  2015-12-11       Impact factor: 15.336

7.  Copper-Catalyzed Borylative Cross-Coupling of Allenes and Imines: Selective Three-Component Assembly of Branched Homoallyl Amines.

Authors:  James Rae; Kay Yeung; Joseph J W McDouall; David J Procter
Journal:  Angew Chem Int Ed Engl       Date:  2015-12-03       Impact factor: 15.336

8.  Cu-catalyzed C-C bond formation of vinylidene cyclopropanes with carbon nucleophiles.

Authors:  Jichao Chen; Shang Gao; Ming Chen
Journal:  Chem Sci       Date:  2019-10-09       Impact factor: 9.825

  8 in total

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