Literature DB >> 12703783

Regiocontrolled Ru-catalyzed addition of carboxylic acids to alkynes: practical protocols for the synthesis of vinyl esters.

Lukas J Goossen1, Jens Paetzold, Debasis Koley.   

Abstract

The catalytic activity of commercially available, air and water stable ruthenium complexes in the addition of carboxylic acids to terminal alkynes was found to be drastically enhanced by the addition of small quantities of base. Moreover, the regioselectivity of the reaction can be controlled by the choice of the base so that both the Markovnikov (Na2CO3) and the anti-Markovnikov products (DMAP) are now easily accessible in excellent selectivities.

Entities:  

Year:  2003        PMID： 12703783

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


  15 in total

1.  Recent advances in the synthetic and mechanistic aspects of the ruthenium-catalyzed carbon-heteroatom bond forming reactions of alkenes and alkynes.

Authors:  Chae S Yi
Journal:  J Organomet Chem       Date:  2011-01-01       Impact factor: 2.369

2.  Stereoselective synthesis of tertiary ethers through geometric control of highly substituted oxocarbenium ions.

Authors:  Lei Liu; Paul E Floreancig
Journal:  Angew Chem Int Ed Engl       Date:  2010-08-09       Impact factor: 15.336

3.  Depolymerizable Poly(O-vinyl carbamate-alt-sulfones) as Customizable Macromolecular Scaffolds for Mucosal Drug Delivery.

Authors:  Kaushlendra Kumar; Eduard Jimenez Castaño; Andrew R Weidner; Adem Yildirim; Andrew P Goodwin
Journal:  ACS Macro Lett       Date:  2016-05-04       Impact factor: 6.903

4.  Total synthesis of neopeltolide and analogs.

Authors:  Yubo Cui; Wangyang Tu; Paul E Floreancig
Journal:  Tetrahedron       Date:  2010-06-26       Impact factor: 2.457

5.  Cyclopropane compatibility with oxidative carbocation formation: total synthesis of clavosolide A.

Authors:  GuangRong Peh; Paul E Floreancig
Journal:  Org Lett       Date:  2012-10-24       Impact factor: 6.005

6.  Oxidative carbocation formation in macrocycles: synthesis of the neopeltolide macrocycle.

Authors:  Wangyang Tu; Paul E Floreancig
Journal:  Angew Chem Int Ed Engl       Date:  2009       Impact factor: 15.336

Review 7.  Metal vinylidenes as catalytic species in organic reactions.

Authors:  Barry M Trost; Andrew McClory
Journal:  Chem Asian J       Date:  2008-02-01

8.  Dinuclear zinc-catalyzed asymmetric desymmetrization of acyclic 2-substituted-1,3-propanediols: a powerful entry into chiral building blocks.

Authors:  Barry M Trost; Sushant Malhotra; Takashi Mino; Naomi S Rajapaksa
Journal:  Chemistry       Date:  2008       Impact factor: 5.236

9.  A general ligand design for gold catalysis allowing ligand-directed anti-nucleophilic attack of alkynes.

Authors:  Yanzhao Wang; Zhixun Wang; Yuxue Li; Gongde Wu; Zheng Cao; Liming Zhang
Journal:  Nat Commun       Date:  2014-04-07       Impact factor: 14.919

Review 10.  Contemporary Strategies for the Synthesis of Tetrahydropyran Derivatives: Application to Total Synthesis of Neopeltolide, a Marine Macrolide Natural Product.

Authors:  Haruhiko Fuwa
Journal:  Mar Drugs       Date:  2016-03-25       Impact factor: 5.118
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