Literature DB >> 15673246

Synthesis of highly functionalized furanones via aldol reaction of 3-silyloxyfurans.

Jeffrey D Winkler1, Kyungsoo Oh, Sylvie M Asselin.   

Abstract

[reaction: see text] The stereoselective aldol reaction of 3-silyloxyfurans with aldehydes in the presence of a Lewis acid is described. N-Bromosuccinimide (NBS)-mediated cyclization of the aldol product leads to the formation of the 2,7-dioxa-bicyclo[2.2.1]heptan-3-one ring system, which represents the formal product of hetero Diels-Alder reaction of the furan with the aldehyde.

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Year:  2005        PMID： 15673246     DOI： 10.1021/ol047810q

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


  3 in total

1.  Pt-catalyzed cyclization/migration of propargylic alcohols for the synthesis of 3(2H)-furanones, pyrrolones, indolizines, and indolizinones.

Authors:  Eric M Bunnelle; Cameron R Smith; Sharon K Lee; Surendra W Singaram; Allison J Rhodes; Richmond Sarpong
Journal:  Tetrahedron       Date:  2008-02-28       Impact factor: 2.457

2.  A tandem Mannich addition-palladium catalyzed ring-closing route toward 4-substituted-3(2H)-furanones.

Authors:  Jubi John; Eliza Târcoveanu; Peter G Jones; Henning Hopf
Journal:  Beilstein J Org Chem       Date:  2014-06-27       Impact factor: 2.883

3.  Side-chain modifications of highly functionalized 3(2H)-furanones.

Authors:  Viviani Nardini; Shirley Muniz Machado Rodrigues; Maurício Gomes Constantino; Gil Valdo José da Silva
Journal:  Molecules       Date:  2012-10-16       Impact factor: 4.411
  3 in total

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