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Literature DB >> 21038044

The use of Br/Cl to promote regioselective gold-catalyzed rearrangement of propargylic carboxylates: an efficient synthesis of (1Z, 3E)-1-bromo/chloro-2-carboxy-1,3-dienes.

Abstract

A gold-catalyzed synthesis of 1-bromo/chloro-2-carboxy-1,3-dienes is developed using propargylic carboxylates containing halogenated alkynes as substrates. The reaction is highly diastereoselective, and the halogen atom at the alkyne terminus selectively promotes a 1,2-acyloxy migration. The diene products participate in the Diels-Alder and cross-coupling reactions.

Entities: Chemical Gene

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Year: 2010 PMID： 21038044 PMCID： PMC3160769 DOI： 10.1039/c0cc03669b

Source DB: PubMed Journal: Chem Commun (Camb) ISSN： 1359-7345 Impact factor: 6.222

25 in total

1. Golden carousel in catalysis: the cationic gold/propargylic ester cycle.

Authors: Andrea Correa; Nicolas Marion; Louis Fensterbank; Max Malacria; Steven P Nolan; Luigi Cavallo
Journal: Angew Chem Int Ed Engl Date: 2008 Impact factor: 15.336

2. Gold-catalyzed organic reactions.

Authors: A Stephen K Hashmi
Journal: Chem Rev Date: 2007-06-20 Impact factor: 60.622

Review 3. Coinage metal-assisted synthesis of heterocycles.

Authors: Nitin T Patil; Yoshinori Yamamoto
Journal: Chem Rev Date: 2008-07-09 Impact factor: 60.622

Review 4. Gold-catalyzed organic transformations.

Authors: Zigang Li; Chad Brouwer; Chuan He
Journal: Chem Rev Date: 2008-07-10 Impact factor: 60.622

5. Gold(I)-catalyzed stereoselective olefin cyclopropanation.

Authors: Magnus J Johansson; David J Gorin; Steven T Staben; F Dean Toste
Journal: J Am Chem Soc Date: 2005-12-28 Impact factor: 15.419

6. Pt-catalyzed pentannulations from in situ generated metallo-carbenoids utilizing propargylic esters.

Authors: B A Bhanu Prasad; Francis K Yoshimoto; Richmond Sarpong
Journal: J Am Chem Soc Date: 2005-09-14 Impact factor: 15.419

7. Gold(I)-catalyzed synthesis of (1E,3E)-dienes from propargylic esters.

Authors: Alexander S Dudnik; Todd Schwier; Vladimir Gevorgyan
Journal: J Organomet Chem Date: 2009-02-15 Impact factor: 2.369

8. 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

9. Ruthenium-catalyzed cyclopropanation of alkenes using propargylic carboxylates as precursors of vinylcarbenoids.

Authors: Koji Miki; Kouichi Ohe; Sakae Uemura
Journal: J Org Chem Date: 2003-10-31 Impact factor: 4.354

Review 10. 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

5 in total

1. Rhodium-catalyzed intra- and intermolecular [5 + 2] cycloaddition of 3-acyloxy-1,4-enyne and alkyne with concomitant 1,2-acyloxy migration.

Authors: Xing-Zhong Shu; Xiaoxun Li; Dongxu Shu; Suyu Huang; Casi M Schienebeck; Xin Zhou; Patrick J Robichaux; Weiping Tang
Journal: J Am Chem Soc Date: 2012-03-12 Impact factor: 15.419

Review 2. Rhodium-catalyzed acyloxy migration of propargylic esters in cycloadditions, inspiration from the recent "gold rush".

Authors: Xing-Zhong Shu; Dongxu Shu; Casi M Schienebeck; Weiping Tang
Journal: Chem Soc Rev Date: 2012-12-07 Impact factor: 54.564