Literature DB >> 12696871

Highly selective catalyst-directed pathways to dihydropyrroles from vinyldiazoacetates and imines.

Michael P Doyle1, Ming Yan, Wenhao Hu, Luisa S Gronenberg.   

Abstract

Copper-catalyzed reactions of vinyldiazoacetates with imines occur via a pathway in which the activated imine undergoes electrophilic addition to the vinyldiazo compound, whereas reactions catalyzed by rhodium(II) proceed through a metal carbene to an intermediate iminiumylide. Both pathways exhibit high stereoselectivities.

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Year:  2003        PMID： 12696871     DOI： 10.1021/ja029745q

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


  11 in total

Review 1.  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

2.  A Reactivity-Driven Approach to the Discovery and Development of Gold-Catalyzed Organic Reactions.

Authors:  Nathan D Shapiro; F Dean Toste
Journal:  Synlett       Date:  2010-03-01       Impact factor: 2.454

3.  Catalytic Enantio- and Diastereoselective Cyclopropanation of 2-Azadienes for the Synthesis of Aminocyclopropanes Bearing Quaternary Carbon Stereogenic Centers.

Authors:  Xinxin Shao; Steven J Malcolmson
Journal:  Org Lett       Date:  2019-08-29       Impact factor: 6.005

4.  Vinyldiazolactone as a vinylcarbene precursor: Highly selective C-H insertion and cyclopropanation reactions.

Authors:  Darren Bykowski; Kou-Hui Wu; Michael P Doyle
Journal:  J Am Chem Soc       Date:  2006-12-20       Impact factor: 15.419

Review 5.  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

6.  Rhodium-catalyzed enantioselective vinylogous addition of enol ethers to vinyldiazoacetates.

Authors:  Austin G Smith; Huw M L Davies
Journal:  J Am Chem Soc       Date:  2012-10-29       Impact factor: 15.419

7.  Lewis acid catalyzed indole synthesis via intramolecular nucleophilic attack of phenyldiazoacetates to iminium ions.

Authors:  Lei Zhou; Michael P Doyle
Journal:  J Org Chem       Date:  2009-12-04       Impact factor: 4.354

8.  Divergent outcomes of carbene transfer reactions from dirhodium- and copper-based catalysts separately or in combination.

Authors:  Xinfang Xu; Wen-Hao Hu; Peter Y Zavalij; Michael P Doyle
Journal:  Angew Chem Int Ed Engl       Date:  2011-10-06       Impact factor: 15.336

9.  Synthesis of azepines by a gold-catalyzed intermolecular [4 + 3]-annulation.

Authors:  Nathan D Shapiro; F Dean Toste
Journal:  J Am Chem Soc       Date:  2008-06-25       Impact factor: 15.419

Review 10.  Recent applications of the divinylcyclopropane-cycloheptadiene rearrangement in organic synthesis.

Authors:  Sebastian Krüger; Tanja Gaich
Journal:  Beilstein J Org Chem       Date:  2014-01-16       Impact factor: 2.883
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