Literature DB >> 18547051

Rh-catalyzed intermolecular cyclopropanation with alpha-alkyl-alpha-diazoesters: catalyst-dependent chemo- and diastereoselectivity.

Patricia Panne1, Andrew DeAngelis, Joseph M Fox.   

Abstract

A Rh-catalyzed procedure for the cyclopropanation of alkenes with alpha-alkyl-alpha-diazoesters is described. With dirhodium tetraoctanoate, the predominant pathway is beta-hydride elimination. While a number of sterically demanding carboxylate ligands serve to avoid beta-hydride elimination, it was found that triphenylacetate (TPA) also imparts high diastereoselectivity.

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Year:  2008        PMID： 18547051      PMCID： PMC2696156          DOI： 10.1021/ol800983y

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


  13 in total

1.  A Convenient Method for the Preparation of (Z)-alpha,beta-Unsaturated Carbonyl Compounds.

Authors:  Douglass F. Taber; R. Jason Herr; Shawn K. Pack; John M. Geremia
Journal:  J Org Chem       Date:  1996-04-19       Impact factor: 4.354

2.  Stereoselective cyclopropanation reactions.

Authors:  Hélène Lebel; Jean-François Marcoux; Carmela Molinaro; André B Charette
Journal:  Chem Rev       Date:  2003-04       Impact factor: 60.622

3.  Catalytic enantioselective C-H activation by means of metal-carbenoid-induced C-H insertion.

Authors:  Huw M L Davies; Rohan E J Beckwith
Journal:  Chem Rev       Date:  2003-08       Impact factor: 60.622

4.  Rh-catalyzed intermolecular reactions of alkynes with alpha-diazoesters that possess beta-hydrogens: ligand-based control over divergent pathways.

Authors:  Patricia Panne; Joseph M Fox
Journal:  J Am Chem Soc       Date:  2007-01-10       Impact factor: 15.419

5.  Cyclopropyl alkynes as mechanistic probes to distinguish between vinyl radical and ionic intermediates.

Authors:  Stephen E Gottschling; Tina N Grant; Kaarina K Milnes; Michael C Jennings; Kim M Baines
Journal:  J Org Chem       Date:  2005-04-01       Impact factor: 4.354

6.  Expanding the scope of C-H amination through catalyst design.

Authors:  Christine G Espino; Kristin Williams Fiori; Mihyong Kim; J Du Bois
Journal:  J Am Chem Soc       Date:  2004-12-01       Impact factor: 15.419

7.  Isotope effects and the nature of selectivity in rhodium-catalyzed cyclopropanations.

Authors:  Daniel T Nowlan; Timothy M Gregg; Huw M L Davies; Daniel A Singleton
Journal:  J Am Chem Soc       Date:  2003-12-24       Impact factor: 15.419

8.  Cyclopentane construction by Rh-catalyzed intramolecular C-h insertion: relative reactivity of a range of catalysts.

Authors:  Douglass F Taber; Pramod V Joshi
Journal:  J Org Chem       Date:  2004-06-11       Impact factor: 4.354

9.  Catalyst and ring size effects on periselectivity of oxonium ylide rearrangements.

Authors:  Fredrik P Marmsäter; John A Vanecko; F G West
Journal:  Org Lett       Date:  2004-05-13       Impact factor: 6.005

10.  Rh-catalyzed formation of dioxolanes from alpha-alkyl diazoesters: diastereoselective cycloadditions of carbonyl ylides with selectivity over beta-hydride elimination.

Authors:  Andrew DeAngelis; Patricia Panne; Glenn P A Yap; Joseph M Fox
Journal:  J Org Chem       Date:  2008-01-12       Impact factor: 4.354
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  13 in total

1.  Stereoselective Synthesis of Bicyclo[6.1.0]nonene Precursors of the Bioorthogonal Reagents s-TCO and BCN.

Authors:  Jessica G K O'Brien; Srinivasa R Chintala; Joseph M Fox
Journal:  J Org Chem       Date:  2017-12-06       Impact factor: 4.354

2.  Radical Cation Cyclopropanations via Chromium Photooxidative Catalysis.

Authors:  Francisco J Sarabia; Eric M Ferreira
Journal:  Org Lett       Date:  2017-05-12       Impact factor: 6.005

3.  Expedient synthesis of fused azepine derivatives using a sequential rhodium(II)-catalyzed cyclopropanation/1-aza-Cope rearrangement of dienyltriazoles.

Authors:  Erica E Schultz; Vincent N G Lindsay; Richmond Sarpong
Journal:  Angew Chem Int Ed Engl       Date:  2014-07-15       Impact factor: 15.336

4.  Rhodium(II)-catalyzed enantioselective C-H functionalization of indoles.

Authors:  Andrew DeAngelis; Valerie W Shurtleff; Olga Dmitrenko; Joseph M Fox
Journal:  J Am Chem Soc       Date:  2011-01-25       Impact factor: 15.419

5.  Rh-Catalyzed Intermolecular Reactions of α-Alkyl-α-Diazo Carbonyl Compounds with Selectivity over β-Hydride Migration.

Authors:  Andrew DeAngelis; Robert Panish; Joseph M Fox
Journal:  Acc Chem Res       Date:  2015-12-21       Impact factor: 22.384

6.  Directed carbozincation reactions of cyclopropene derivatives.

Authors:  Vinod Tarwade; Xiaozhong Liu; Ni Yan; Joseph M Fox
Journal:  J Am Chem Soc       Date:  2009-04-22       Impact factor: 15.419

7.  Rh(2)(S-PTTL)(3)TPA-A Mixed Ligand Dirhodium(II) Catalyst for Enantioselective Reactions of α-Alkyl-α-Diazoesters.

Authors:  David T Boruta; Olga Dmitrenko; Glenn P A Yap; Joseph M Fox
Journal:  Chem Sci       Date:  2012-05       Impact factor: 9.825

8.  Unusually reactive and selective carbonyl ylides for three-component cycloaddition reactions.

Authors:  Andrew DeAngelis; Michael T Taylor; Joseph M Fox
Journal:  J Am Chem Soc       Date:  2009-01-28       Impact factor: 15.419

9.  Rh(II)-Catalyzed Reactions of Diazoesters with Organozinc Reagents.

Authors:  Robert Panish; Ramajeyam Selvaraj; Joseph M Fox
Journal:  Org Lett       Date:  2015-08-04       Impact factor: 6.005

10.  Enantioselective synthesis of cyclobutanes via sequential Rh-catalyzed bicyclobutanation/Cu-catalyzed homoconjugate addition.

Authors:  Robert Panish; Srinivasa R Chintala; David T Boruta; Yinzhi Fang; Michael T Taylor; Joseph M Fox
Journal:  J Am Chem Soc       Date:  2013-06-12       Impact factor: 15.419
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