Literature DB >> 19283501

Synthesis and palladium-catalysed isomerisation of fused polycyclic tetrahydrofurans: efficient and stereoselective one-pot domino construction of functionalised bridged bicyclo[n.2.1] ring systems.

Pierre-Yves Roger1, Fabien Blondeau, David Bensa, Thierry Constantieux, Jean Rodriguez.   

Abstract

A new one-pot domino reaction for a general entry to functionalised bridged bicyclo[n.2.1] ring systems from alpha, alpha'-diactivated cyclic ketones and trans-1,4-dihalides is described. The sequence combines a base promoted C-O cycloalkylation reaction leading to fused polycyclic enol ethers and their in situ palladium-catalysed isomerisation.

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Year:  2009        PMID： 19283501     DOI： 10.1007/s11030-009-9131-2

Source DB:  PubMed          Journal:  Mol Divers        ISSN： 1381-1991            Impact factor:   2.943


  13 in total

1.  C-C versus C-O anionic domino cycloalkylation of stabilized carbanions: facile one-pot stereoselective preparation of functionalized bridged bicycloalkanones and cyclic enol ethers.

Authors:  T Lavoisier-Gallo; E Charonnet; J M Pons; M Rajzman; R Faure; J Rodriguez
Journal:  Chemistry       Date:  2001-03-02       Impact factor: 5.236

Review 2.  Target-oriented and diversity-oriented organic synthesis in drug discovery.

Authors:  S L Schreiber
Journal:  Science       Date:  2000-03-17       Impact factor: 47.728

3.  Synthesis of Functionalized Bicyclo[3.2.1]octanes and Their Multiple Uses in Organic Chemistry.

Authors:  Marie-Hélène Filippini; Jean Rodriguez
Journal:  Chem Rev       Date:  1999-01-13       Impact factor: 60.622

Review 4.  On inventing reactions for atom economy.

Authors:  Barry M Trost
Journal:  Acc Chem Res       Date:  2002-09       Impact factor: 22.384

5.  Cyclization reactions of dianions in organic synthesis.

Authors:  Peter Langer; Walter Freiberg
Journal:  Chem Rev       Date:  2004-09       Impact factor: 60.622

6.  The atom economy--a search for synthetic efficiency.

Authors:  B M Trost
Journal:  Science       Date:  1991-12-06       Impact factor: 47.728

7.  Efficient and stereoselective synthesis of bicyclo[3.2.1]octan-8-ones: synthesis and palladium-catalyzed isomerization of functionalized 2-vinyl-2,3,3a,4,5,6-hexahydro-2,3-benzofurans.

Authors:  Peter Langer; Edith Holtz; Nehad N R Saleh
Journal:  Chemistry       Date:  2002-02-15       Impact factor: 5.236

8.  Multicomponent synthesis of dihydropyrimidines and thiazines.

Authors:  Danielle J Vugts; Manoe M Koningstein; Rob F Schmitz; Frans J J de Kanter; Marinus B Groen; Romano V A Orru
Journal:  Chemistry       Date:  2006-09-18       Impact factor: 5.236

9.  Multicomponent cycloadditions: the four-component [5+1+2+1] cycloaddition of vinylcyclopropanes, alkynes, and CO.

Authors:  Paul A Wender; Gabriel G Gamber; Robert D Hubbard; Son M Pham; Lei Zhang
Journal:  J Am Chem Soc       Date:  2005-03-09       Impact factor: 15.419

Review 10.  Towards the optimal screening collection: a synthesis strategy.

Authors:  Thomas E Nielsen; Stuart L Schreiber
Journal:  Angew Chem Int Ed Engl       Date:  2008       Impact factor: 15.336
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