Literature DB >> 16522069

Room temperature Au(I)-catalyzed exo-selective cycloisomerization of acetylenic acids: an entry to functionalized gamma-lactones.

Emilie Genin1, Patrick Yves Toullec, Sylvain Antoniotti, Célia Brancour, Jean-Pierre Genêt, Véronique Michelet.   

Abstract

A highly efficient gold-catalyzed cyclization reaction of various functionalized acetylenic acids is described. The cyclizations are conducted in the presence of Au(I) catalyst in acetonitrile at room temperature in a short reaction time. The reaction conditions are compatible with several functional groups, such as ester, alkene, alkyne, chloro, and free or protected alcohol, and lead to original gamma-lactones in good to excellent yields.

Entities:  

Year:  2006        PMID： 16522069     DOI： 10.1021/ja056857j

Source DB:  PubMed          Journal:  J Am Chem Soc        ISSN： 0002-7863            Impact factor:   15.419


  15 in total

1.  Recent Advances in Transition Metal-Catalyzed Glycosylation.

Authors:  Matthew J McKay; Hien M Nguyen
Journal:  ACS Catal       Date:  2012-06-14       Impact factor: 13.084

2.  Gold(III)- versus gold(I)-induced cyclization: synthesis of six-membered mesoionic carbene and acyclic (aryl)(heteroaryl) carbene complexes.

Authors:  Gaël Ung; Michele Soleilhavoup; Guy Bertrand
Journal:  Angew Chem Int Ed Engl       Date:  2012-11-21       Impact factor: 15.336

3.  Self-assembled nanospheres with multiple endohedral binding sites pre-organize catalysts and substrates for highly efficient reactions.

Authors:  Qi-Qiang Wang; Sergio Gonell; Stefan H A M Leenders; Maximilian Dürr; Ivana Ivanović-Burmazović; Joost N H Reek
Journal:  Nat Chem       Date:  2016-01-11       Impact factor: 24.427

4.  Development of a Modular Synthetic Route to (+)-Pleuromutilin, (+)-12-epi-Mutilins, and Related Structures.

Authors:  Mingshuo Zeng; Stephen K Murphy; Seth B Herzon
Journal:  J Am Chem Soc       Date:  2017-11-02       Impact factor: 15.419

5.  Enantioselective synthesis of alkyne-substituted quaternary carbon stereogenic centers through NHC-Cu-catalyzed allylic substitution reactions with (i-Bu)2(alkynyl)aluminum reagents.

Authors:  Jennifer A Dabrowski; Fang Gao; Amir H Hoveyda
Journal:  J Am Chem Soc       Date:  2011-03-08       Impact factor: 15.419

6.  Au-Cavitands: Size governed arene-alkyne cycloisomerization.

Authors:  Lisa E Rusali; Michael P Schramm
Journal:  Tetrahedron Lett       Date:  2020-08-16       Impact factor: 2.415

7.  Assembly of four diverse heterocyclic libraries enabled by Prins cyclization, Au-catalyzed enyne cycloisomerization, and automated amide synthesis.

Authors:  Jiayue Cui; David I Chai; Christopher Miller; Jason Hao; Christopher Thomas; JingQi Wang; Karl A Scheidt; Sergey A Kozmin
Journal:  J Org Chem       Date:  2012-08-16       Impact factor: 4.354

8.  A biosynthetically inspired synthesis of (-)-berkelic acid and analogs.

Authors:  Christopher F Bender; Christopher L Paradise; Vincent M Lynch; Francis K Yoshimoto; Jef K De Brabander
Journal:  Tetrahedron       Date:  2018-01-12       Impact factor: 2.457

9.  Regioselectivity Influences in Platinum-Catalyzed Intramolecular Alkyne O-H and N-H Additions.

Authors:  Jeff P Costello; Eric M Ferreira
Journal:  Org Lett       Date:  2019-12-09       Impact factor: 6.072

10.  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
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