Literature DB >> 19624120

Nickel-catalyzed borylative ring opening of vinyl epoxides and aziridines.

Stefano Crotti1, Ferruccio Bertolini, Franco Macchia, Mauro Pineschi.   

Abstract

A mild ring opening of vinyl epoxides and aziridines with B(2)Pin(2) catalyzed by Ni(0)-Binap affords new functionalized allylic boron derivatives which undergo sequential transformations. The uncatalyzed allylation of aldehydes allows obtaining challenging bishomoallylic alicyclic 1,3-diols and 1,3-amino alcohols with remarkably high stereoselectivities. Valuable trans-bisallylic 1,4-amino alcohols can be obtained by a simple oxidation.

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Year:  2009        PMID： 19624120     DOI： 10.1021/ol901429g

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


  9 in total

1.  Nickel-catalyzed allylic substitution of simple alkenes.

Authors:  Ryosuke Matsubara; Timothy F Jamison
Journal:  Chem Asian J       Date:  2011-03-08

2.  Ni- and Pd-catalyzed synthesis of substituted and functionalized allylic boronates.

Authors:  Ping Zhang; Ian A Roundtree; James P Morken
Journal:  Org Lett       Date:  2012-02-29       Impact factor: 6.005

3.  Nickel-Catalyzed Stereoselective Arylboration of Unactivated Alkenes.

Authors:  Kaitlyn M Logan; Stephen R Sardini; Sean D White; M Kevin Brown
Journal:  J Am Chem Soc       Date:  2017-12-22       Impact factor: 15.419

4.  Ni-Catalyzed Arylboration of Unactivated Alkenes: Scope and Mechanistic Studies.

Authors:  Stephen R Sardini; Alison L Lambright; Grace L Trammel; Humair M Omer; Peng Liu; M Kevin Brown
Journal:  J Am Chem Soc       Date:  2019-06-04       Impact factor: 15.419

5.  Diastereo- and Enantioselective Iridium Catalyzed Coupling of Vinyl Aziridines with Alcohols: Site-Selective Modification of Unprotected Diols and Synthesis of Substituted Piperidines.

Authors:  Gang Wang; Jana Franke; Chinh Q Ngo; Michael J Krische
Journal:  J Am Chem Soc       Date:  2015-06-15       Impact factor: 15.419

6.  Photoredox/Nickel-Catalyzed Single-Electron Tsuji-Trost Reaction: Development and Mechanistic Insights.

Authors:  Jennifer K Matsui; Álvaro Gutiérrez-Bonet; Madeline Rotella; Rauful Alam; Osvaldo Gutierrez; Gary A Molander
Journal:  Angew Chem Int Ed Engl       Date:  2018-11-07       Impact factor: 15.336

7.  Synthesis of novel 5-alkyl/aryl/heteroaryl substituted diethyl 3,4-dihydro-2H-pyrrole-4,4-dicarboxylates by aziridine ring expansion of 2-[(aziridin-1-yl)-1-alkyl/aryl/heteroaryl-methylene]malonic acid diethyl esters.

Authors:  Satish S More; T Krishna Mohan; Y Sateesh Kumar; U K Syam Kumar; Navin B Patel
Journal:  Beilstein J Org Chem       Date:  2011-06-20       Impact factor: 2.883

8.  Copper-Catalyzed Ring-Opening Reactions of Alkyl Aziridines with B2pin2: Experimental and Computational Studies.

Authors:  Lucilla Favero; Andrea Menichetti; Cosimo Boldrini; Lucrezia Margherita Comparini; Valeria Di Bussolo; Sebastiano Di Pietro; Mauro Pineschi
Journal:  Molecules       Date:  2021-12-06       Impact factor: 4.411

9.  Redox-triggered C-C coupling of alcohols and vinyl epoxides: diastereo- and enantioselective formation of all-carbon quaternary centers via tert-(hydroxy)-prenylation.

Authors:  Jiajie Feng; Victoria J Garza; Michael J Krische
Journal:  J Am Chem Soc       Date:  2014-06-10       Impact factor: 15.419
  9 in total

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