Literature DB >> 19128053

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

Andrew DeAngelis1, Michael T Taylor, Joseph M Fox.   

Abstract

Conditions are described for the Rh-catalyzed formation of highly functionalized dihydro- and tetrahydrofuran products via three-component reactions of aldehydes, alpha-alkyl-alpha-diazoesters, and dipolarophiles. The alkyl-substituted carbonyl ylides that are generated in this fashion are highly reactive in cycloaddition reactions and display a scope of reactivity that is much broader than the three-component reactions of carbonyl ylides derived from ethyl diazoacetate or alpha-aryl-alpha-diazoesters. The reactions of alkyl-substituted carbonyl ylides proceed with high regioselectivity and diastereoselectivity that are rationalized in terms of an asynchronous, endo-selective transition state.

Entities:  

Mesh：

Substances：

Year:  2009        PMID： 19128053      PMCID： PMC2659807          DOI： 10.1021/ja807184r

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


  22 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.  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

3.  Highly chemoselective 2,4,5-triaryl-1,3-dioxolane formation from intermolecular 1,3-dipolar addition of carbonyl ylide with aryl aldehydes.

Authors:  Chong-Dao Lu; Zhi-Yong Chen; Hui Liu; Wen-Hao Hu; Ai-Qiao Mi
Journal:  Org Lett       Date:  2004-09-02       Impact factor: 6.005

4.  Cobalt cluster-containing carbonyl ylides for catalytic, three-component assembly of oxygen heterocycles.

Authors:  Aaron J Skaggs; Eleanor Y Lin; Timothy F Jamison
Journal:  Org Lett       Date:  2002-06-27       Impact factor: 6.005

5.  Divergence of carbonyl ylide reactions as a function of diazocarbonyl compound and aldehyde substituent: dioxolanes, dioxolenes, and epoxides.

Authors:  Albert E Russell; Jonathan Brekan; Luisa Gronenberg; Michael P Doyle
Journal:  J Org Chem       Date:  2004-08-06       Impact factor: 4.354

6.  Scope and mechanism for lewis acid-catalyzed cycloadditions of aldehydes and donor-acceptor cyclopropanes: evidence for a stereospecific intimate ion pair pathway.

Authors:  Patrick D Pohlhaus; Shanina D Sanders; Andrew T Parsons; Wei Li; Jeffrey S Johnson
Journal:  J Am Chem Soc       Date:  2008-06-11       Impact factor: 15.419

7.  Multicomponent reactions of diazoamides: diastereoselective synthesis of mono- and bis-spirofurooxindoles.

Authors:  Sengodagounder Muthusamy; Chidambaram Gunanathan; Munirathinam Nethaji
Journal:  J Org Chem       Date:  2004-08-20       Impact factor: 4.354

8.  General access to the vinca and tacaman alkaloids using a Rh(II)-catalyzed cyclization/cycloaddition cascade.

Authors:  Dylan B England; Albert Padwa
Journal:  J Org Chem       Date:  2008-03-05       Impact factor: 4.354

9.  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

10.  Axially chiral BINIM and Ni(II)-catalyzed highly enantioselective 1,3-dipolar cycloaddition reactions of azomethine ylides and N-arylmaleimides.

Authors:  Jing-Wen Shi; Mei-Xin Zhao; Zhi-Yu Lei; Min Shi
Journal:  J Org Chem       Date:  2007-12-05       Impact factor: 4.354
View more
  11 in total

Review 1.  Comprehensive survey of chemical libraries for drug discovery and chemical biology: 2009.

Authors:  Roland E Dolle; Bertrand Le Bourdonnec; Karin Worm; Guillermo A Morales; Craig J Thomas; Wei Zhang
Journal:  J Comb Chem       Date:  2010-10-05

2.  Application of a robustness screen for the evaluation of synthetic organic methodology.

Authors:  Karl D Collins; Andreas Rühling; Frank Glorius
Journal:  Nat Protoc       Date:  2014-05-15       Impact factor: 13.491

3.  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

4.  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

5.  Rh-catalyzed intermolecular reactions of cyclic α-diazocarbonyl compounds with selectivity over tertiary C-H bond migration.

Authors:  Andrew DeAngelis; Olga Dmitrenko; Joseph M Fox
Journal:  J Am Chem Soc       Date:  2012-06-19       Impact factor: 15.419

6.  Synthesis of Secondary Unsaturated Lactams via an Aza-Heck Reaction.

Authors:  Scott A Shuler; Guoyin Yin; Sarah B Krause; Caroline M Vesper; Donald A Watson
Journal:  J Am Chem Soc       Date:  2016-10-18       Impact factor: 15.419

7.  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

8.  Chiral crown conformation of Rh(2)(S-PTTL)(4): enantioselective cyclopropanation with alpha-alkyl-alpha-diazoesters.

Authors:  Andrew DeAngelis; Olga Dmitrenko; Glenn P A Yap; Joseph M Fox
Journal:  J Am Chem Soc       Date:  2009-06-03       Impact factor: 15.419

9.  A Rh(II)-catalyzed highly stereoselective [3 + 2] annulation of vinyl diazoacetates with indole-2-carbaldehyde for the synthesis of indolyl dihydrofurans.

Authors:  Rimei Zheng; Aimin Xu; Jiawu Huang; Zhijing Zhang; Xinru Yin; Tianyuan Zhang; Wenhao Hu; Yu Qian
Journal:  Mol Divers       Date:  2022-01-20       Impact factor: 2.943

10.  Synthesis of bicyclo[3.1.0]hexanes by (3 + 2) annulation of cyclopropenes with aminocyclopropanes.

Authors:  Bastian Muriel; Alec Gagnebin; Jerome Waser
Journal:  Chem Sci       Date:  2019-10-08       Impact factor: 9.825
View more

北京卡尤迪生物科技股份有限公司 © 2022-2023.