Literature DB >> 22621315

Substrate-dependent divergent outcomes from catalytic reactions of silyl-protected enol diazoacetates with nitrile oxides: azabicyclo[3.1.0]hexanes or 5-arylaminofuran-2(3H)-ones.

Xinfang Xu1, Dmitry Shabashov, Peter Y Zavalij, Michael P Doyle.   

Abstract

Dirhodium(II)-catalyzed reactions of silyl-protected enol diazoacetates with nitrile oxides exhibit high nitrile oxide substituent dependence in the production rearrangement products via dipolar cycloaddition and either the Neber rearrangement or the Lossen rearrangement.

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Year:  2012        PMID： 22621315      PMCID： PMC3377374          DOI： 10.1021/jo3006733

Source DB:  PubMed          Journal:  J Org Chem        ISSN： 0022-3263            Impact factor:   4.354


  24 in total

1.  Cascade Processes of Metallo Carbenoids.

Authors:  Albert Padwa; M. David Weingarten
Journal:  Chem Rev       Date:  1996-02-01       Impact factor: 60.622

2.  Highly enantioselective catalytic synthesis of functionalized chiral diazoacetoacetates.

Authors:  Xinfang Xu; Wen-Hao Hu; Michael P Doyle
Journal:  Angew Chem Int Ed Engl       Date:  2011-05-31       Impact factor: 15.336

3.  Continuous flow system with a polymer-supported dirhodium(II) catalyst: application to enantioselective carbonyl ylide cycloaddition reactions.

Authors:  Koji Takeda; Tadashi Oohara; Naoyuki Shimada; Hisanori Nambu; Shunichi Hashimoto
Journal:  Chemistry       Date:  2011-11-17       Impact factor: 5.236

4.  Unexpected catalytic reactions of silyl-protected enol diazoacetates with nitrile oxides that form 5-arylaminofuran-2(3H)-one-4-carboxylates.

Authors:  Xinfang Xu; Dmitry Shabashov; Peter Y Zavalij; Michael P Doyle
Journal:  Org Lett       Date:  2012-01-24       Impact factor: 6.005

5.  Controlling factors for C-H functionalization versus cyclopropanation of dihydronaphthalenes.

Authors:  Etienne Nadeau; Dominic L Ventura; Jonathan A Brekan; Huw M L Davies
Journal:  J Org Chem       Date:  2010-03-19       Impact factor: 4.354

6.  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

7.  Rhodium(II)-catalyzed asymmetric sulfur(VI) reduction of diazo sulfonylamidines.

Authors:  Nicklas Selander; Valery V Fokin
Journal:  J Am Chem Soc       Date:  2012-01-27       Impact factor: 15.419

8.  A strategy to synthesize taxol side chain and (-)-epi cytoxazone via chiral Brønsted acid-Rh(2)(OAc)(4) co-catalyzed enantioselective three-component reactions.

Authors:  Yu Qian; Xinfang Xu; Liqin Jiang; Dipak Prajapati; Wenhao Hu
Journal:  J Org Chem       Date:  2010-11-05       Impact factor: 4.354

9.  Pericyclic reaction of a zwitterionic salt of an enedione-diazoester. A novel strategy for the synthesis of highly functionalized resorcinols.

Authors:  Yu Liu; Kanwarpal Bakshi; Peter Zavalij; Michael P Doyle
Journal:  Org Lett       Date:  2010-10-01       Impact factor: 6.005

10.  Asymmetric [4 + 3] cycloadditions between vinylcarbenoids and dienes: application to the total synthesis of the natural product (-)-5-epi-vibsanin E.

Authors:  Brett D Schwartz; Justin R Denton; Yajing Lian; Huw M L Davies; Craig M Williams
Journal:  J Am Chem Soc       Date:  2009-06-17       Impact factor: 15.419
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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.  Efficient synthesis of oxazoles by dirhodium(II)-catalyzed reactions of styryl diazoacetate with oximes.

Authors:  Xinfang Xu; Peter Y Zavalij; Wenhao Hu; Michael P Doyle
Journal:  Chem Commun (Camb)       Date:  2012-12-07       Impact factor: 6.222

3.  Vinylogous reactivity of enol diazoacetates with donor-acceptor substituted hydrazones. Synthesis of substituted pyrazole derivatives.

Authors:  Xinfang Xu; Peter Y Zavalij; Wenhao Hu; Michael P Doyle
Journal:  J Org Chem       Date:  2013-01-24       Impact factor: 4.354

4.  Dirhodium(II)-Catalyzed Annulation of Enoldiazoacetamides with α-Diazoketones: An Efficient and Highly Selective Approach to Fused and Bridged Ring Systems.

Authors:  Qing-Qing Cheng; Julietta Yedoyan; Hadi Arman; Michael P Doyle
Journal:  Angew Chem Int Ed Engl       Date:  2016-03-23       Impact factor: 15.336

5.  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 in total

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