Literature DB >> 23317097

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

Xichen Xu1, Yu Qian, Peter Y Zavalij, Michael P Doyle.   

Abstract

Transition-metal catalysts direct 1,2-C→C, -O→C, and -N→C migrations from β-methylene-β-silyloxy-β-amido-α-diazoacetates with high selectivity. The key to achieving this unique display of differential selectivities relies on steric and stereoelectronic control by their catalytically generated metal carbenes.

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Year:  2013        PMID： 23317097      PMCID： PMC3572838          DOI： 10.1021/ja311392m

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


  51 in total

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Authors:  B M Trost; T Yasukata
Journal:  J Am Chem Soc       Date:  2001-07-25       Impact factor: 15.419

2.  Metal-catalyzed [1,2]-alkyl shift in allenyl ketones: synthesis of multisubstituted furans.

Authors:  Alexander S Dudnik; Vladimir Gevorgyan
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3.  Heterocycles from gold catalysis.

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Journal:  Org Lett       Date:  2007-01-04       Impact factor: 6.005

5.  Multifunctionalized 3-hydroxypyrroles in a three-step, one-pot cascade process from methyl 3-TBSO-2-diazo-3-butenoate and nitrones.

Authors:  Xinfang Xu; Maxim O Ratnikov; Peter Y Zavalij; Michael P Doyle
Journal:  Org Lett       Date:  2011-10-27       Impact factor: 6.005

6.  Rearrangement pathways of 2-hydroxy-2-methylpropylidene: an experimental and computational study.

Authors:  Robin A Farlow; Dasan M Thamattoor; R B Sunoj; Christopher M Hadad
Journal:  J Org Chem       Date:  2002-05-17       Impact factor: 4.354

7.  Catalytic enantioselective 1,3-dipolar cycloaddition of C,N-cyclic azomethine imines with alpha,beta-unsaturated aldehydes.

Authors:  Takuya Hashimoto; Yuko Maeda; Masato Omote; Hiroki Nakatsu; Keiji Maruoka
Journal:  J Am Chem Soc       Date:  2010-03-31       Impact factor: 15.419

8.  Metal-catalyzed 1,2-shift of diverse migrating groups in allenyl systems as a new paradigm toward densely functionalized heterocycles.

Authors:  Alexander S Dudnik; Anna W Sromek; Marina Rubina; Joseph T Kim; Alexander V Kel'in; Vladimir Gevorgyan
Journal:  J Am Chem Soc       Date:  2008-01-04       Impact factor: 15.419

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

Authors:  Nathan D Shapiro; Yun Shi; F Dean Toste
Journal:  J Am Chem Soc       Date:  2009-08-26       Impact factor: 15.419

10.  Rhodium(II)- and copper(II)-catalyzed reactions of enol diazoacetates with nitrones: metal carbene versus Lewis acid directed pathways.

Authors:  Yu Qian; Xinfang Xu; Xiaochen Wang; Peter J Zavalij; Wenhao Hu; Michael P Doyle
Journal:  Angew Chem Int Ed Engl       Date:  2012-05-04       Impact factor: 15.336
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  5 in total

Review 1.  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

2.  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

3.  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

4.  The [3 + 3]-cycloaddition alternative for heterocycle syntheses: catalytically generated metalloenolcarbenes as dipolar adducts.

Authors:  Xinfang Xu; Michael P Doyle
Journal:  Acc Chem Res       Date:  2014-03-20       Impact factor: 22.384

5.  1,2-N-migration in a gold-catalysed synthesis of functionalised indenes by the 1,1-carboalkoxylation of ynamides.

Authors:  Holly V Adcock; Thomas Langer; Paul W Davies
Journal:  Chemistry       Date:  2014-05-14       Impact factor: 5.236
  5 in total

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