Literature DB >> 19645449

Gold-catalyzed [3+3]-annulation of azomethine imines with propargyl esters.

Nathan D Shapiro1, Yun Shi, F Dean Toste.   

Abstract

The gold-catalyzed [3+3]-cycloaddition reaction of propargyl esters and azomethine imines has been developed. The reaction provides a rapid entry into a wide range of substituted tetrahydropyridazine derivatives from simple starting materials. A stepwise mechanism involving addition of the 1,3-dipole to a gold-carbenoid intermediate is proposed.

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Year:  2009        PMID： 19645449      PMCID： PMC2763378          DOI： 10.1021/ja903863b

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


  21 in total

1.  Gold(I)-catalyzed oxidative rearrangements.

Authors:  Cole A Witham; Pablo Mauleón; Nathan D Shapiro; Benjamin D Sherry; F Dean Toste
Journal:  J Am Chem Soc       Date:  2007-04-14       Impact factor: 15.419

Review 2.  Relativistic effects in homogeneous gold catalysis.

Authors:  David J Gorin; F Dean Toste
Journal:  Nature       Date:  2007-03-22       Impact factor: 49.962

3.  Gold-catalyzed organic reactions.

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

4.  Au-containing all-carbon 1,4-dipoles: generation and [4 + 2] annulation in the formation of carbo-/heterocycles.

Authors:  Guozhu Zhang; Xiaogen Huang; Guotao Li; Liming Zhang
Journal:  J Am Chem Soc       Date:  2008-01-19       Impact factor: 15.419

Review 5.  Gold-catalyzed cycloisomerizations of enynes: a mechanistic perspective.

Authors:  Eloísa Jiménez-Núñez; Antonio M Echavarren
Journal:  Chem Rev       Date:  2008-07-18       Impact factor: 60.622

6.  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

7.  Pt(II)- or Au(III)-catalyzed [3+2] cycloaddition of metal-containing azomethine ylides: highly efficient synthesis of the mitosene skeleton.

Authors:  Hiroyuki Kusama; Yuichi Miyashita; Jun Takaya; Nobuharu Iwasawa
Journal:  Org Lett       Date:  2006-01-19       Impact factor: 6.005

8.  AuCl(3)-catalyzed benzannulation: synthesis of naphthyl ketone derivatives from o-alkynylbenzaldehydes with alkynes.

Authors:  Naoki Asao; Kumiko Takahashi; Sunyoung Lee; Taisuke Kasahara; Yoshinori Yamamoto
Journal:  J Am Chem Soc       Date:  2002-10-30       Impact factor: 15.419

9.  Au-containing all-carbon 1,3-dipoles: generation and [3+2] cycloaddition reactions.

Authors:  Guozhu Zhang; Liming Zhang
Journal:  J Am Chem Soc       Date:  2008-08-28       Impact factor: 15.419

10.  Fluorenes and styrenes by Au(I)-catalyzed annulation of enynes and alkynes.

Authors:  David J Gorin; Iain D G Watson; F Dean Toste
Journal:  J Am Chem Soc       Date:  2008-03-06       Impact factor: 15.419
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  24 in total

1.  Asymmeric formal [3 + 3]-cycloaddition reactions of nitrones with electrophilic vinylcarbene intermediates.

Authors:  Xiaochen Wang; Xinfang Xu; Peter Y Zavalij; Michael P Doyle
Journal:  J Am Chem Soc       Date:  2011-09-27       Impact factor: 15.419

2.  Gold(I)-catalyzed enantioselective [3+2] and [3+3] cycloaddition reactions of propargyl acetals/ketals.

Authors:  Cristina Navarro; Nathan D Shapiro; Maurizio Bernasconi; Takahiro Horibe; F Dean Toste
Journal:  Tetrahedron       Date:  2015-09-02       Impact factor: 2.457

3.  Phosphine-catalyzed annulations of azomethine imines: allene-dependent [3 + 2], [3 + 3], [4 + 3], and [3 + 2 + 3] pathways.

Authors:  Risong Na; Chengfeng Jing; Qihai Xu; Hui Jiang; Xi Wu; Jiayan Shi; Jiangchun Zhong; Min Wang; Diego Benitez; Ekaterina Tkatchouk; William A Goddard; Hongchao Guo; Ohyun Kwon
Journal:  J Am Chem Soc       Date:  2011-08-03       Impact factor: 15.419

4.  Highly enantioselective dearomatizing formal [3+3] cycloaddition reactions of N-acyliminopyridinium ylides with electrophilic enol carbene intermediates.

Authors:  Xinfang Xu; Peter Y Zavalij; Michael P Doyle
Journal:  Angew Chem Int Ed Engl       Date:  2013-10-02       Impact factor: 15.336

Review 5.  Catalytic asymmetric cycloaddition reactions of enoldiazo compounds.

Authors:  Kostiantyn O Marichev; Michael P Doyle
Journal:  Org Biomol Chem       Date:  2019-04-24       Impact factor: 3.876

6.  Gold(I)-catalyzed diastereo- and enantioselective 1,3-dipolar cycloaddition and Mannich reactions of azlactones.

Authors:  Asa D Melhado; Giovanni W Amarante; Z Jane Wang; Marco Luparia; F Dean Toste
Journal:  J Am Chem Soc       Date:  2011-02-22       Impact factor: 15.419

Review 7.  Cycloaddition reactions of enoldiazo compounds.

Authors:  Qing-Qing Cheng; Yongming Deng; Marianne Lankelma; Michael P Doyle
Journal:  Chem Soc Rev       Date:  2017-08-29       Impact factor: 54.564

8.  Dirhodium(II)-catalyzed formal [3+2+1]-annulation of azomethine imines with two molecules of a diazo ketone.

Authors:  Xinfang Xu; Xichen Xu; Peter Y Zavalij; Michael P Doyle
Journal:  Chem Commun (Camb)       Date:  2013-04-07       Impact factor: 6.222

9.  Highly selective catalyst-dependent competitive 1,2-C→C, -O→C, and -N→C migrations from β-methylene-β-silyloxy-β-amido-α-diazoacetates.

Authors:  Xichen Xu; Yu Qian; Peter Y Zavalij; Michael P Doyle
Journal:  J Am Chem Soc       Date:  2013-01-17       Impact factor: 15.419

10.  Bicyclic pyrazolidinone derivatives from diastereoselective catalytic [3 + 3]-cycloaddition reactions of enoldiazoacetates with azomethine imines.

Authors:  Yu Qian; Peter J Zavalij; Wenhao Hu; Michael P Doyle
Journal:  Org Lett       Date:  2013-03-11       Impact factor: 6.005
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