Literature DB >> 14599176

The development of a facile tandem Wolff/Cope rearrangement for the synthesis of fused carbocyclic skeletons.

Richmond Sarpong1, Julius T Su, Brian M Stoltz.   

Abstract

A set of mild processes for the conversion of vinyl cyclopropyl diazo ketones to highly functionalized cycloheptadienones and vinyl cyclopentenones by use of a target-inspired tandem Wolff/Cope rearrangement sequence is described. A divergent reaction course of the vinyl cyclopropyl diazo ketone substrates under sono- or photochemical activation provides good to excellent yields (55-98%) of the product cycloheptadienones and vinyl cyclopentenones.

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Year:  2003        PMID： 14599176     DOI： 10.1021/ja037587c

Source DB:  PubMed          Journal:  J Am Chem Soc        ISSN： 0002-7863            Impact factor:   15.419


  9 in total

1.  Wolff/Cope Approach to the AB Ring of the Sesterterpenoid Variecolin.

Authors:  Michael R Krout; Christopher E Henry; Thomas Jensen; Kun-Liang Wu; Scott C Virgil; Brian M Stoltz
Journal:  J Org Chem       Date:  2018-01-23       Impact factor: 4.354

Review 2.  Toward a symphony of reactivity: cascades involving catalysis and sigmatropic rearrangements.

Authors:  Amanda C Jones; Jeremy A May; Richmond Sarpong; Brian M Stoltz
Journal:  Angew Chem Int Ed Engl       Date:  2014-03-03       Impact factor: 15.336

3.  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

4.  PREPARATION OF ISOPROPYL 2-DIAZOACETYL(PHENYL)CARBAMATE.

Authors:  Hubert Muchalski; Amanda B Doody; Timothy L Troyer; Jeffrey N Johnston
Journal:  Organic Synth       Date:  2011-02-08

5.  Computational Prediction of One-Step Synthesis of Seven-membered Fused Rings by (5+2) Cycloaddition Utilising Cycloalkenes.

Authors:  Chen-Chen Zhou; Xiao-Na Ke; Xiu-Fang Xu
Journal:  Sci Rep       Date:  2015-07-22       Impact factor: 4.379

Review 6.  Recent applications of the divinylcyclopropane-cycloheptadiene rearrangement in organic synthesis.

Authors:  Sebastian Krüger; Tanja Gaich
Journal:  Beilstein J Org Chem       Date:  2014-01-16       Impact factor: 2.883

7.  An unusual stereoretentive 1,3-quaternary carbon shift resulting in an enantioselective RhII-catalyzed formal [4+1]-cycloaddition between diazo compounds and vinyl ketenes.

Authors:  Kevin X Rodriguez; Tara C Pilato; Brandon L Ashfeld
Journal:  Chem Sci       Date:  2018-02-19       Impact factor: 9.825

8.  Synthesis of bicyclo[3.1.0]hexanes by (3 + 2) annulation of cyclopropenes with aminocyclopropanes.

Authors:  Bastian Muriel; Alec Gagnebin; Jerome Waser
Journal:  Chem Sci       Date:  2019-10-08       Impact factor: 9.825

9.  Metal-free tandem carbene N-H insertions and C-C bond cleavages.

Authors:  Pu Chen; Jiang Nan; Yan Hu; Yifan Kang; Bo Wang; Yangmin Ma; Michal Szostak
Journal:  Chem Sci       Date:  2020-11-10       Impact factor: 9.825
  9 in total

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