Literature DB >> 17465562

Gold-catalyzed cyclization of allene-substituted malonate esters: synthesis of beta,gamma-unsaturated delta-lactones.

Julio Piera1, Patrik Krumlinde, Dirk Strübing, Jan-E Bäckvall.   

Abstract

An efficient method for the preparation of beta,gamma-unsaturated delta-lactones has been developed. The starting materials for the synthesis of these compounds are allene-substituted malonates which undergo gold-catalyzed cyclization by means of nucleophilic attack of the ester moiety on the allene. It is worth mentioning that this is the first example where an ester group attacks as a nucleophile in a gold-catalyzed transformation of allenes.

Entities:  

Year:  2007        PMID: 17465562     DOI: 10.1021/ol070793v

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


  3 in total

1.  Mechanistic study of gold(I)-catalyzed intermolecular hydroamination of allenes.

Authors:  Z Jane Wang; Diego Benitez; Ekaterina Tkatchouk; William A Goddard; F Dean Toste
Journal:  J Am Chem Soc       Date:  2010-09-22       Impact factor: 15.419

2.  Mechanistic studies on Au(I)-catalyzed [3,3]-sigmatropic rearrangements using cyclopropane probes.

Authors:  Pablo Mauleón; Jamin L Krinsky; F Dean Toste
Journal:  J Am Chem Soc       Date:  2009-04-01       Impact factor: 15.419

Review 3.  Ligand effects in homogeneous Au catalysis.

Authors:  David J Gorin; Benjamin D Sherry; F Dean Toste
Journal:  Chem Rev       Date:  2008-07-25       Impact factor: 60.622

  3 in total

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