Literature DB >> 27459685

The B(C6F5)3-Catalyzed Tandem Meinwald Rearrangement-Reductive Amination.

Martine R Tiddens1, Robertus J M Klein Gebbink1, Matthias Otte1.   

Abstract

A system of three coupled catalytic cycles enabling the one-pot transformation of epoxides to amines via Meinwald rearrangement, imine condensation, and imine reduction is described. This assisted tandem catalysis is catalyzed by B(C6F5)3 resulting in the first tandem Meinwald rearrangement-reductive amination protocol. The reaction proceeds in nondried solvents and yields β-functionalized amines. In particular, β-diarylamines are obtained in high yields.

Entities:  

Year:  2016        PMID: 27459685     DOI: 10.1021/acs.orglett.6b01744

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


  3 in total

1.  Late-stage chemoselective functional-group manipulation of bioactive natural products with super-electrophilic silylium ions.

Authors:  Trandon A Bender; Philippa R Payne; Michel R Gagné
Journal:  Nat Chem       Date:  2017-09-18       Impact factor: 24.427

2.  Expanding Water/Base Tolerant Frustrated Lewis Pair Chemistry to Alkylamines Enables Broad Scope Reductive Aminations.

Authors:  Valerio Fasano; Michael J Ingleson
Journal:  Chemistry       Date:  2017-01-18       Impact factor: 5.236

3.  Acid-Catalyzed Rearrangements of 3-Aryloxirane-2-Carboxamides: Novel DFT Mechanistic Insights.

Authors:  Zheng-Wang Qu; Hui Zhu; Sergey A Katsyuba; Vera L Mamedova; Vakhid A Mamedov; Stefan Grimme
Journal:  ChemistryOpen       Date:  2020-07-01       Impact factor: 2.911

  3 in total

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