Literature DB >> 22426113

Programmable enantioselective one-pot synthesis of molecules with eight stereocenters.

Marco Potowski1, Markus Schürmann, Hans Preut, Andrey P Antonchick, Herbert Waldmann.   

Abstract

We developed an enantioselectively catalyzed tandem synthesis of structurally and stereochemically complex molecules that forms four carbon-carbon bonds and sets eight stereocenters with high regio-, diastereo- and enantioselectivity. It can be programmed to yield different stereoisomers by varying only the order of combination of a common set of reagents and catalysts. We report what is to our knowledge the first synthesis of both enantiomers of a chiral compound using the same chiral catalyst.

Entities:  

Mesh:

Substances:

Year:  2012        PMID: 22426113     DOI: 10.1038/nchembio.901

Source DB:  PubMed          Journal:  Nat Chem Biol        ISSN: 1552-4450            Impact factor:   15.040


  13 in total

1.  Highly enantioselective synthesis and cellular evaluation of spirooxindoles inspired by natural products.

Authors:  Andrey P Antonchick; Claas Gerding-Reimers; Mario Catarinella; Markus Schürmann; Hans Preut; Slava Ziegler; Daniel Rauh; Herbert Waldmann
Journal:  Nat Chem       Date:  2010-07-11       Impact factor: 24.427

2.  Charting biologically relevant chemical space: a structural classification of natural products (SCONP).

Authors:  Marcus A Koch; Ansgar Schuffenhauer; Michael Scheck; Stefan Wetzel; Marco Casaulta; Alex Odermatt; Peter Ertl; Herbert Waldmann
Journal:  Proc Natl Acad Sci U S A       Date:  2005-11-21       Impact factor: 11.205

3.  Control of four stereocentres in a triple cascade organocatalytic reaction.

Authors:  Dieter Enders; Matthias R M Hüttl; Christoph Grondal; Gerhard Raabe
Journal:  Nature       Date:  2006-06-15       Impact factor: 49.962

4.  Construction of enantiopure pyrrolidine ring system via asymmetric [3+2]-cycloaddition of azomethine ylides.

Authors:  Ganesh Pandey; Prabal Banerjee; Smita R Gadre
Journal:  Chem Rev       Date:  2006-11       Impact factor: 60.622

Review 5.  Enantioselective copper-catalyzed 1,3-dipolar cycloadditions.

Authors:  Levi M Stanley; Mukund P Sibi
Journal:  Chem Rev       Date:  2008-07-10       Impact factor: 60.622

6.  Highly enantioselective copper(I)-fesulphos-catalyzed 1,3-dipolar cycloaddition of azomethine ylides.

Authors:  Silvia Cabrera; Ramón Gómez Arrayás; Juan C Carretero
Journal:  J Am Chem Soc       Date:  2005-11-30       Impact factor: 15.419

7.  4,7-diphenylisobenzofuran: a useful intermediate for the construction of phenyl-substituted acenes.

Authors:  James Eric Rainbolt; Glen P Miller
Journal:  J Org Chem       Date:  2007-03-21       Impact factor: 4.354

8.  Brønsted-acid-catalyzed asymmetric multicomponent reactions for the facile synthesis of highly enantioenriched structurally diverse nitrogenous heterocycles.

Authors:  Jie Yu; Feng Shi; Liu-Zhu Gong
Journal:  Acc Chem Res       Date:  2011-07-29       Impact factor: 22.384

9.  Novel dipolarophiles and dipoles in the metal-catalyzed enantioselective 1,3-dipolar cycloaddition of azomethine ylides.

Authors:  Javier Adrio; Juan C Carretero
Journal:  Chem Commun (Camb)       Date:  2011-04-06       Impact factor: 6.222

10.  Synthesis of natural-product-like molecules with over eighty distinct scaffolds.

Authors:  Daniel Morton; Stuart Leach; Christopher Cordier; Stuart Warriner; Adam Nelson
Journal:  Angew Chem Int Ed Engl       Date:  2009       Impact factor: 15.336

View more
  5 in total

Review 1.  The chemistry of isoindole natural products.

Authors:  Klaus Speck; Thomas Magauer
Journal:  Beilstein J Org Chem       Date:  2013-10-10       Impact factor: 2.883

2.  Additive-assisted regioselective 1,3-dipolar cycloaddition of azomethine ylides with benzylideneacetone.

Authors:  Chuqin Peng; Jiwei Ren; Jun-An Xiao; Honggang Zhang; Hua Yang; Yiming Luo
Journal:  Beilstein J Org Chem       Date:  2014-02-07       Impact factor: 2.883

3.  Intramolecular Hydrogen Bond Activation: Thiourea-Organocatalyzed Enantioselective 1,3-Dipolar Cycloaddition of Salicylaldehyde-Derived Azomethine Ylides with Nitroalkenes.

Authors:  Francisco Esteban; Wioleta Cieślik; Enrique M Arpa; Andrea Guerrero-Corella; Sergio Díaz-Tendero; Josefina Perles; José A Fernández-Salas; Alberto Fraile; José Alemán
Journal:  ACS Catal       Date:  2018-01-31       Impact factor: 13.084

4.  Catalytic enantioselective 1,3-dipolar cycloadditions of azomethine ylides for biology-oriented synthesis.

Authors:  Rishikesh Narayan; Marco Potowski; Zhi-Jun Jia; Andrey P Antonchick; Herbert Waldmann
Journal:  Acc Chem Res       Date:  2014-03-22       Impact factor: 22.384

5.  Natural products chemistry: The emerging trends and prospective goals.

Authors:  Riaz A Khan
Journal:  Saudi Pharm J       Date:  2018-02-07       Impact factor: 4.330

  5 in total

北京卡尤迪生物科技股份有限公司 © 2022-2023.