Literature DB >> 16146369

Unusual gold(I)-catalyzed isomerization of 3-hydroxylated 1,5-enynes: highly substrate-dependent reaction manifolds.

Fabien Gagosz1.   

Abstract

[reaction: see text] The gold(I) isomerization of diversely substituted 3-hydroxylated enynes has led to the discovery of three new unreported skeletal rearrangements furnishing structures such as alkylidene-cyclopentenes, cyclohexadienes or alpha,beta-unsaturated aldehydes under very mild conditions.

Entities:  

Year:  2005        PMID： 16146369     DOI： 10.1021/ol051397k

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


  7 in total

1.  Gold-catalyzed cycloisomerization of 1,5-allenynes via dual activation of an ene reaction.

Authors:  Paul Ha-Yeon Cheong; Philip Morganelli; Michael R Luzung; K N Houk; F Dean Toste
Journal:  J Am Chem Soc       Date:  2008-03-08       Impact factor: 15.419

2.  Asymmetric Au-catalyzed cycloisomerization of 1,6-enynes: An entry to bicyclo[4.1.0]heptene.

Authors:  Alexandre Pradal; Chung-Meng Chao; Patrick Y Toullec; Véronique Michelet
Journal:  Beilstein J Org Chem       Date:  2011-07-26       Impact factor: 2.883

3.  When gold can do what iodine cannot do: A critical comparison.

Authors:  Sara Hummel; Stefan F Kirsch
Journal:  Beilstein J Org Chem       Date:  2011-06-22       Impact factor: 2.883

4.  Gold(I)-Catalyzed Activation of Alkynes for the Construction of Molecular Complexity.

Authors:  Ruth Dorel; Antonio M Echavarren
Journal:  Chem Rev       Date:  2015-04-06       Impact factor: 60.622

Review 5.  Gold-catalyzed cyclizations of alkynol-based compounds: synthesis of natural products and derivatives.

Authors:  Benito Alcaide; Pedro Almendros; José M Alonso
Journal:  Molecules       Date:  2011-09-13       Impact factor: 4.411

6.  Divergent reaction pathways in gold-catalyzed cycloisomerization of 1,5-enynes containing a cyclopropane ring: dramatic ortho substituent and temperature effects.

Authors:  Gen-Qiang Chen; Wei Fang; Yin Wei; Xiang-Ying Tang; Min Shi
Journal:  Chem Sci       Date:  2016-03-04       Impact factor: 9.825

7.  Use of N-methylformamide as a solvent in indium-promoted Barbier reactions en route to enediyne and epoxy diyne formation: comparison of rate and stereoselectivity in C-C bond-forming reactions with water.

Authors:  Kwame Frimpong; Joseph Wzorek; Claire Lawlor; Katharine Spencer; Thomas Mitzel
Journal:  J Org Chem       Date:  2009-08-21       Impact factor: 4.354
  7 in total

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