Literature DB >> 28090124

Practical Synthetic Procedures for the Iron-Catalyzed Intermolecular Olefin Aminohydroxylation Using Functionalized Hydroxylamines.

Cheng-Liang Zhu1, Deng-Fu Lu1, Jeffrey D Sears1, Zhen-Xin Jia1, Hao Xu1.   

Abstract

A set of practical synthetic procedures for the iron-catalyzed intermolecular olefin aminohydroxylation reactions in gram scale is reported. In these transformations, a bench-stable functionalized hydroxylamine is applied as the amination reagent. This method is compatible with a broad range of synthetically valuable olefins including those that are incompatible with the existing aminohydroxylation methods. It also provides valuable amino alcohol building blocks with regio- and stereo-chemical arrays that are complementary to known methods.

Entities:  

Keywords:  alkenes; amination; asymmetric catalysis; iron; oxidation

Year:  2016        PMID: 28090124      PMCID: PMC5226647          DOI: 10.1055/s-0035-1562515

Source DB:  PubMed          Journal:  Synthesis (Stuttg)        ISSN: 0039-7881            Impact factor:   3.157


  16 in total

1.  Copper(II)-catalyzed aminohydroxylation of olefins.

Authors:  David J Michaelis; Christopher J Shaffer; Tehshik P Yoon
Journal:  J Am Chem Soc       Date:  2007-01-30       Impact factor: 15.419

2.  Pd-catalyzed intermolecular ortho-C-H amidation of anilides by N-nosyloxycarbamate.

Authors:  Ka-Ho Ng; Albert S C Chan; Wing-Yiu Yu
Journal:  J Am Chem Soc       Date:  2010-09-22       Impact factor: 15.419

3.  Copper catalyzed enantioselective intramolecular aminooxygenation of alkenes.

Authors:  Peter H Fuller; Jin-Woo Kim; Sherry R Chemler
Journal:  J Am Chem Soc       Date:  2008-12-31       Impact factor: 15.419

4.  Osmium-catalyzed vicinal oxyamination of alkenes by N-(4-toluenesulfonyloxy)carbamates.

Authors:  Anthony C Willis; Malcolm D McLeod
Journal:  J Org Chem       Date:  2012-09-24       Impact factor: 4.354

5.  Synthesis of 7-azabicyclo[2.2.1]heptane and 2-oxa-4-azabicyclo[3.3.1]non-3-ene derivatives by base-promoted heterocyclization of alkyl N-(cis(trans)-3,trans(cis)-4-dibromocyclohex-1-yl)carbamates and N-(cis(trans)-3,trans(cis)-4-dibromocyclohex-1-yl)-2,2,2-trifluoroacetamides.

Authors:  Elena Gómez-Sanchez; Elena Soriano; José Marco-Contelles
Journal:  J Org Chem       Date:  2007-10-10       Impact factor: 4.354

6.  Iron(II)-catalyzed asymmetric intramolecular aminohydroxylation of indoles.

Authors:  Yong-Qiang Zhang; Yong-An Yuan; Guan-Sai Liu; Hao Xu
Journal:  Org Lett       Date:  2013-07-22       Impact factor: 6.005

7.  Iron(II)-catalyzed intramolecular aminohydroxylation of olefins with functionalized hydroxylamines.

Authors:  Guan-Sai Liu; Yong-Qiang Zhang; Yong-An Yuan; Hao Xu
Journal:  J Am Chem Soc       Date:  2013-02-20       Impact factor: 15.419

8.  Iron-Catalyzed Diastereoselective Intramolecular Olefin Aminobromination with Bromide Ion.

Authors:  Jun-Shan Tian; Cheng-Liang Zhu; Yun-Rong Chen; Hao Xu
Journal:  Synthesis (Stuttg)       Date:  2015-06       Impact factor: 3.157

9.  Stereoselective radical azidooxygenation of alkenes.

Authors:  Bo Zhang; Armido Studer
Journal:  Org Lett       Date:  2013-08-09       Impact factor: 6.005

10.  Iron(II)-catalyzed intramolecular olefin aminofluorination.

Authors:  Deng-Fu Lu; Guan-Sai Liu; Cheng-Liang Zhu; Bo Yuan; Hao Xu
Journal:  Org Lett       Date:  2014-05-14       Impact factor: 6.005

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