Literature DB >> 21384818

Microwave assisted synthesis of bridgehead alkenes.

Leah Cleary1, Hoseong Yoo, Kenneth J Shea.   

Abstract

A new, concise method to synthesize triene precursors for the type 2 intramolecular Diels-Alder reaction has been developed. Microwave irradiation of the trienes provides a convenient method for the synthesis of bridgehead alkenes. Higher yields, shorter reaction times, and lower reaction temperatures provide a general and efficient route to this interesting class of molecules.

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Year:  2011        PMID： 21384818      PMCID： PMC3064725          DOI： 10.1021/ol200244p

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


  8 in total

1.  The Type 2 Intramolecular Diels-Alder Reaction: Synthesis and Chemistry of Bridgehead Alkenes.

Authors:  Brian R. Bear; Steven M. Sparks; Kenneth J. Shea
Journal:  Angew Chem Int Ed Engl       Date:  2001-03-02       Impact factor: 15.336

2.  Type 2 intramolecular N-acylazo Diels-Alder reaction: regio- and stereoselective synthesis of bridgehead bicyclic 1,2-diazines.

Authors:  Claudia L Molina; Chun P Chow; Kenneth J Shea
Journal:  J Org Chem       Date:  2007-08-04       Impact factor: 4.354

3.  Bridged to Fused Ring Interchange. Methodology for the Construction of Fused Cycloheptanes and Cyclooctanes. Total Syntheses of Ledol, Ledene, and Compressanolide.

Authors:  S. L. Gwaltney II; S. T. Sakata; K. J. Shea
Journal:  J Org Chem       Date:  1996-10-18       Impact factor: 4.354

4.  An approach to the synthesis of stenine.

Authors:  Liang Zhu; Ryan Lauchli; Mandy Loo; Kenneth J Shea
Journal:  Org Lett       Date:  2007-05-10       Impact factor: 6.005

5.  Dual function catalysts. Dehydrogenation and asymmetric intramolecular Diels-Alder cycloaddition of N-hydroxy formate esters and hydroxamic acids: evidence for a ruthenium-acylnitroso intermediate.

Authors:  Chun P Chow; Kenneth J Shea
Journal:  J Am Chem Soc       Date:  2005-03-23       Impact factor: 15.419

6.  Type 2 intramolecular N-acylnitroso Diels-Alder reaction: scope and application to the synthesis of medium ring lactams.

Authors:  Steven M Sparks; Chun P Chow; Liang Zhu; Kenneth J Shea
Journal:  J Org Chem       Date:  2004-04-30       Impact factor: 4.354

7.  Synthesis of the bicyclic welwitindolinone core via an alkylation/cyclization cascade reaction.

Authors:  John A Brailsford; Ryan Lauchli; Kenneth J Shea
Journal:  Org Lett       Date:  2009-11-19       Impact factor: 6.005

8.  Total synthesis of (+/-)-haouamine A.

Authors:  Phil S Baran; Noah Z Burns
Journal:  J Am Chem Soc       Date:  2006-03-29       Impact factor: 15.419
  8 in total
  1 in total

1.  Design and Synthesis of a New Class of Twin-Chain Amphiphiles for Self-Assembled Monolayer-based Electrochemical Biosensor Applications.

Authors:  Thomas J Fisher; Socrates Jose P Cañete; Rebecca Y Lai; Patrick H Dussault
Journal:  European J Org Chem       Date:  2013-06-01
  1 in total

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