Literature DB >> 18980330

Convenient access to bicyclic and tricyclic diazenes.

Douglass F Taber1, Pengfei Guo.   

Abstract

Heating the tosylhydrazone of an omega-alkenyl ketone or aldehyde to reflux in toluene in the presence of K(2)CO(3) delivered the bicyclic diazene. Irradiation of the diazene converted it to the cyclopropane. This appears to be a generally useful method for the construction of substituted cyclopentanes and cyclohexanes.

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Year:  2008        PMID： 18980330      PMCID： PMC2765546          DOI： 10.1021/jo8017704

Source DB:  PubMed          Journal:  J Org Chem        ISSN： 0022-3263            Impact factor:   4.354


  8 in total

1.  Diastereoselective cyclopentane construction

Authors: 
Journal:  J Org Chem       Date:  2000-06-16       Impact factor: 4.354

2.  Highly efficient synthesis of tricyclic amines by a cyclization/cycloaddition cascade: total syntheses of aspidospermine, aspidospermidine, and quebrachamine.

Authors:  Iain Coldham; Adam J M Burrell; Laura E White; Harry Adams; Niall Oram
Journal:  Angew Chem Int Ed Engl       Date:  2007       Impact factor: 15.336

3.  Use of optically active cyclic N,N-dialkyl aminals in asymmetric induction.

Authors:  M E Jung; A Huang
Journal:  Org Lett       Date:  2000-08-24       Impact factor: 6.005

4.  A simple and general chiral silicon Lewis acid for asymmetric synthesis: highly enantioselective [3+2] acylhydrazone-enol ether cycloadditions.

Authors:  Seiji Shirakawa; Pamela J Lombardi; James L Leighton
Journal:  J Am Chem Soc       Date:  2005-07-20       Impact factor: 15.419

5.  Two-step formal [3+2] cycloaddition of enones/enals and allenyl MOM ether: gold-catalyzed highly diastereoselective synthesis of cyclopentanone enol ether containing an all-carbon quaternary center.

Authors:  Xiaogen Huang; Liming Zhang
Journal:  J Am Chem Soc       Date:  2007-05-02       Impact factor: 15.419

6.  Enantioselective total synthesis of pyrinodemin A.

Authors:  Annie Pouilhès; Anel Florès Amado; Anne Vidal; Yves Langlois; Cyrille Kouklovsky
Journal:  Org Biomol Chem       Date:  2008-03-10       Impact factor: 3.876

7.  Effect of substitution on the intramolecular 1,3-dipolar cycloaddition of alkene tethered münchnones.

Authors:  Guillaume Bélanger; Myriam April; Etienne Dauphin; Stéphanie Roy
Journal:  J Org Chem       Date:  2007-02-16       Impact factor: 4.354

8.  A convenient synthesis of substituted pyrazolidines and azaproline derivatives through highly regio- and diastereoselective reduction of 2-pyrazolines.

Authors:  Jesús M de Los Santos; Yago López; Domitila Aparicio; Francisco Palacios
Journal:  J Org Chem       Date:  2007-12-18       Impact factor: 4.354
  8 in total
  3 in total

1.  Intramolecular [1 + 4 + 1] cycloaddition: establishment of the method.

Authors:  Douglass F Taber; Pengfei Guo; Na Guo
Journal:  J Am Chem Soc       Date:  2010-08-18       Impact factor: 15.419

2.  Formal and total synthesis of (±)-cycloclavine.

Authors:  Nitinkumar D Jabre; Teruki Watanabe; Matthias Brewer
Journal:  Tetrahedron Lett       Date:  2014-01-01       Impact factor: 2.415

3.  Construction of NH-Unprotected Spiropyrrolidines and Spiroisoindolines by [4+1] Cyclizations of γ-Azidoboronic Acids with Cyclic N-Sulfonylhydrazones.

Authors:  Lucía López; María-Paz Cabal; Carlos Valdés
Journal:  Angew Chem Int Ed Engl       Date:  2021-11-25       Impact factor: 16.823
  3 in total

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