Literature DB >> 22272728

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

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

Abstract

Silyl-protected enol diazoacetates undergo dirhodium(II)-catalyzed reactions with nitrile oxides to form acid-labile ketenimines via dipolar cycloaddition of nitrile oxides to a donor/acceptor cyclopropene and Lossen rearrangement of the dipolar adduct; acid catalysis converts the ketenimine to the furan product.
© 2012 American Chemical Society

Entities:  

Mesh：

Substances：

Year:  2012        PMID： 22272728      PMCID： PMC3273040          DOI： 10.1021/ol203331r

Source DB:  PubMed          Journal:  Org Lett        ISSN： 1523-7052            Impact factor:   6.005


  26 in total

1.  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

2.  A divergent mechanistic course of Pd(0)-catalyzed aza-Claisen rearrangement and aza-Rautenstrauch-type cyclization of N-allyl ynamides.

Authors:  Kyle A Dekorver; Richard P Hsung; Andrew G Lohse; Yu Zhang
Journal:  Org Lett       Date:  2010-04-16       Impact factor: 6.005

3.  N-allyl-N-sulfonyl ynamides as synthetic precursors to amidines and vinylogous amidines. An unexpected N-to-C 1,3-sulfonyl shift in nitrile synthesis.

Authors:  Kyle A DeKorver; Whitney L Johnson; Yu Zhang; Richard P Hsung; Huifang Dai; Jun Deng; Andrew G Lohse; Yan-Shi Zhang
Journal:  J Org Chem       Date:  2011-05-24       Impact factor: 4.354

4.  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

5.  D2-symmetric dirhodium catalyst derived from a 1,2,2-triarylcyclopropanecarboxylate ligand: design, synthesis and application.

Authors:  Changming Qin; Vyacheslav Boyarskikh; Jørn H Hansen; Kenneth I Hardcastle; Djamaladdin G Musaev; Huw M L Davies
Journal:  J Am Chem Soc       Date:  2011-11-02       Impact factor: 15.419

6.  Nitrenes, carbenes, diradicals, and ylides. Interconversions of reactive intermediates.

Authors:  Curt Wentrup
Journal:  Acc Chem Res       Date:  2011-03-31       Impact factor: 22.384

7.  Three-component reaction of N'-(2-alkynylbenzylidene)hydrazide, alkyne, with sulfonyl azide via a multicatalytic process: a novel and concise approach to 2-amino-H-pyrazolo[5,1-a]isoquinolines.

Authors:  Shaoyu Li; Yong Luo; Jie Wu
Journal:  Org Lett       Date:  2011-07-26       Impact factor: 6.005

8.  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

9.  Copper(I)-catalyzed three component reaction of sulfonyl azide, alkyne, and nitrone cycloaddition/rearrangement cascades: a novel one-step synthesis of imidazolidin-4-ones.

Authors:  Kayambu Namitharan; Kasi Pitchumani
Journal:  Org Lett       Date:  2011-10-12       Impact factor: 6.005

10.  Carbonyldiimidazole-mediated Lossen rearrangement.

Authors:  Pascal Dubé; Noah F Fine Nathel; Michael Vetelino; Michel Couturier; Claude Larrivée Aboussafy; Simon Pichette; Matthew L Jorgensen; Mark Hardink
Journal:  Org Lett       Date:  2009-12-17       Impact factor: 6.005
View more
  7 in total

1.  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

2.  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.

Authors:  Xinfang Xu; Dmitry Shabashov; Peter Y Zavalij; Michael P Doyle
Journal:  J Org Chem       Date:  2012-06-04       Impact factor: 4.354

Review 3.  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

4.  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

5.  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

6.  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

7.  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
  7 in total

北京卡尤迪生物科技股份有限公司 © 2022-2023.