Literature DB >> 16802803

A highly efficient preparative method of alpha-ylidene-beta-diketones via Au(III)-catalyzed acyl migration of propargylic esters.

Shaozhong Wang1, Liming Zhang.   

Abstract

A highly efficient synthesis of alpha-alkylidene or benzylidene-beta-diketones from readily available propargylic esters has been developed. The proposed key transformation is a novel intramolecular acyl migration to nucleophilic AuIII-C(sp2) bonds. Noteworthy features of this method are its efficiency and stereoselectivity. The yields of this reaction were mostly close to quantitative, and high to excellent stereoselectivities were observed in the cases of dienyl beta-diketones.

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Year:  2006        PMID： 16802803     DOI： 10.1021/ja062777j

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


  23 in total

1.  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.

Authors:  Yanzhao Wang; Biao Lu; Liming Zhang
Journal:  Chem Commun (Camb)       Date:  2010-10-29       Impact factor: 6.222

Review 2.  Toward a symphony of reactivity: cascades involving catalysis and sigmatropic rearrangements.

Authors:  Amanda C Jones; Jeremy A May; Richmond Sarpong; Brian M Stoltz
Journal:  Angew Chem Int Ed Engl       Date:  2014-03-03       Impact factor: 15.336

Review 3.  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

4.  Substituent Effect on the Formation and Their Reactivity of Platinum Carbenoids.

Authors:  Eun Jin Cho; Daesung Lee
Journal:  Adv Synth Catal       Date:  2008-11-17       Impact factor: 5.837

5.  Synthesis of highly functionalized cyclohexenone rings: rhodium-catalyzed 1,3-acyloxy migration and subsequent [5+1] cycloaddition.

Authors:  Dongxu Shu; Xiaoxun Li; Min Zhang; Patrick J Robichaux; Weiping Tang
Journal:  Angew Chem Int Ed Engl       Date:  2010-12-29       Impact factor: 15.336

Review 6.  Metal-catalyzed double migratory cascade reactions of propargylic esters and phosphates.

Authors:  Roohollah Kazem Shiroodi; Vladimir Gevorgyan
Journal:  Chem Soc Rev       Date:  2013-06-21       Impact factor: 54.564

7.  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

8.  Mechanistically diverse copper-, silver-, and gold-catalyzed acyloxy and phosphatyloxy migrations: efficient synthesis of heterocycles via cascade migration/cycloisomerization approach.

Authors:  Todd Schwier; Anna W Sromek; Dahrika M L Yap; Dmitri Chernyak; Vladimir Gevorgyan
Journal:  J Am Chem Soc       Date:  2007-07-21       Impact factor: 15.419

9.  Mechanistic insights into the gold-catalyzed cycloisomerization of bromoallenyl ketones: ligand-controlled regioselectivity.

Authors:  Yuanzhi Xia; Alexander S Dudnik; Vladimir Gevorgyan; Yahong Li
Journal:  J Am Chem Soc       Date:  2008-05-08       Impact factor: 15.419

10.  Gold-catalyzed double migration-benzannulation cascade toward naphthalenes.

Authors:  Alexander S Dudnik; Todd Schwier; Vladimir Gevorgyan
Journal:  Org Lett       Date:  2008-03-01       Impact factor: 6.005
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