Literature DB >> 19072074

Stereoselective synthesis of dienes from N-allylhydrazones.

Devon A Mundal1, Kelly E Lutz, Regan J Thomson.   

Abstract

A new method for the stereoselective synthesis of dienes from aldehydes and N-allylhydrazine derivatives has been developed. High levels of (E)-stereoselectivity are obtained for a variety of substrates. Addition of a dienophile to the reaction mixture allows a one-flask diene synthesis-cycloaddition sequence.

Entities:  

Year:  2009        PMID： 19072074     DOI： 10.1021/ol802585r

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


  6 in total

1.  Synthetic strategy: without a trace.

Authors:  Sarah E Steinhardt; Christopher D Vanderwal
Journal:  Nat Chem       Date:  2010-04       Impact factor: 24.427

2.  Nickel-catalyzed allylic substitution of simple alkenes.

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

3.  Triflimide-catalysed sigmatropic rearrangement of N-allylhydrazones as an example of a traceless bond construction.

Authors:  Devon A Mundal; Christopher T Avetta; Regan J Thomson
Journal:  Nat Chem       Date:  2010-02-28       Impact factor: 24.427

4.  Intramolecular polar [4(⊕)+2] cycloadditions of aryl-1-aza-2-azoniaallene salts: unprecedented reactivity leading to polycyclic protonated azomethine imines.

Authors:  Daniel A Bercovici; Jodi M Ogilvie; Nikolay Tsvetkov; Matthias Brewer
Journal:  Angew Chem Int Ed Engl       Date:  2013-11-11       Impact factor: 15.336

5.  A Diverted Aerobic Heck Reaction Enables Selective 1,3-Diene and 1,3,5-Triene Synthesis through C-C Bond Scission.

Authors:  Neil J McAlpine; Long Wang; Brad P Carrow
Journal:  J Am Chem Soc       Date:  2018-10-15       Impact factor: 15.419

6.  Catalytic 1,2-dihydronaphthalene and E-aryl-diene synthesis via CoIII-Carbene radical and o-quinodimethane intermediates.

Authors:  Colet Te Grotenhuis; Braja G Das; Petrus F Kuijpers; Wouter Hageman; Mees Trouwborst; Bas de Bruin
Journal:  Chem Sci       Date:  2017-10-12       Impact factor: 9.825
  6 in total

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