Literature DB >> 24025195

Rh2(R-TPCP)4-catalyzed enantioselective [3+2]-cycloaddition between nitrones and vinyldiazoacetates.

Changming Qin1, Huw M L Davies.   

Abstract

Rhodium-catalyzed reaction of vinyldiazoacetates with nitrones results in a formal [3+2]-cycloaddition to generate 2,5-dihydroisoxazoles with high levels of asymmetric induction. The cascade reaction begins with a vinylogous addition event, followed by an iminium addition ring-closure/hydride migration/alkene isomerization cascade. Dirhodium tetrakis(triarylcyclopropanecarboxylates) are the optimum catalysts for this process.

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Year:  2013        PMID： 24025195      PMCID： PMC3952076          DOI： 10.1021/ja4069003

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


  25 in total

1.  Highly regio- and stereoselective dirhodium vinylcarbene induced nitrone cycloaddition with subsequent cascade carbenoid aromatic cycloaddition/N-O cleavage and rearrangement.

Authors:  Xiaochen Wang; Quentin M Abrahams; Peter Y Zavalij; Michael P Doyle
Journal:  Angew Chem Int Ed Engl       Date:  2012-04-26       Impact factor: 15.336

2.  On the mechanism and selectivity of the combined C-H activation/Cope rearrangement.

Authors:  Jørn H Hansen; Timothy M Gregg; Stephanie R Ovalles; Yajing Lian; Jochen Autschbach; Huw M L Davies
Journal:  J Am Chem Soc       Date:  2011-03-08       Impact factor: 15.419

3.  Alkynoate synthesis through the vinylogous reactivity of rhodium(II) carbenoids.

Authors:  Damien Valette; Yajing Lian; John P Haydek; Kenneth I Hardcastle; Huw M L Davies
Journal:  Angew Chem Int Ed Engl       Date:  2012-07-16       Impact factor: 15.336

4.  Gold-catalyzed formal [3 + 3] and [4 + 2] cycloaddition reactions of nitrosobenzenes with alkenylgold carbenoids.

Authors:  Vinayak Vishnu Pagar; Appaso Mahadev Jadhav; Rai-Shung Liu
Journal:  J Am Chem Soc       Date:  2011-12-05       Impact factor: 15.419

5.  Enantioselective double C-H activation of dihydronaphthalenes.

Authors:  Huw M L Davies; Qihui Jin
Journal:  Org Lett       Date:  2005-06-09       Impact factor: 6.005

6.  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

7.  Pyridine activation via copper(I)-catalyzed annulation toward indolizines.

Authors:  José Barluenga; Giacomo Lonzi; Lorena Riesgo; Luis A López; Miguel Tomás
Journal:  J Am Chem Soc       Date:  2010-09-29       Impact factor: 15.419

8.  Enantioselective synthesis of 2-arylbicyclo[1.1.0]butane carboxylates.

Authors:  Changming Qin; Huw M L Davies
Journal:  Org Lett       Date:  2013-01-03       Impact factor: 6.005

9.  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

10.  The combined C-H functionalization/Cope rearrangement: discovery and applications in organic synthesis.

Authors:  Huw M L Davies; Yajing Lian
Journal:  Acc Chem Res       Date:  2012-05-11       Impact factor: 22.384
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  11 in total

1.  Reversal of the regiochemistry in the rhodium-catalyzed [4+3] cycloaddition between vinyldiazoacetates and dienes.

Authors:  Pablo E Guzmán; Yajing Lian; Huw M L Davies
Journal:  Angew Chem Int Ed Engl       Date:  2014-09-29       Impact factor: 15.336

Review 2.  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

3.  Enantioselective Dirhodium(II)-Catalyzed Cyclopropanations with Trimethylsilylethyl and Trichloroethyl Aryldiazoacetates.

Authors:  Solymar Negretti; Carolyn M Cohen; Jane J Chang; David M Guptill; Huw M L Davies
Journal:  Tetrahedron       Date:  2015-06-02       Impact factor: 2.457

4.  A Stereoselective [3+1] Ring Expansion for the Synthesis of Highly Substituted Methylene Azetidines.

Authors:  Steven C Schmid; Ilia A Guzei; Jennifer M Schomaker
Journal:  Angew Chem Int Ed Engl       Date:  2017-09-01       Impact factor: 15.336

5.  Aziridinium Ylides: Underutilized Intermediates for Complex Amine Synthesis.

Authors:  Hillary J Dequina; Jennifer M Schomaker
Journal:  Trends Chem       Date:  2020-09-02

Review 6.  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

7.  Silver-catalyzed vinylogous fluorination of vinyl diazoacetates.

Authors:  Changming Qin; Huw M L Davies
Journal:  Org Lett       Date:  2013-11-14       Impact factor: 6.005

8.  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

9.  Synthesis of azasilacyclopentenes and silanols via Huisgen cycloaddition-initiated C-H bond insertion cascades.

Authors:  Jiun-Le Shih; Santa Jansone-Popova; Christopher Huynh; Jeremy A May
Journal:  Chem Sci       Date:  2017-09-04       Impact factor: 9.825

10.  Blue light-promoted photolysis of aryldiazoacetates.

Authors:  Igor D Jurberg; Huw M L Davies
Journal:  Chem Sci       Date:  2018-05-22       Impact factor: 9.825
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