Literature DB >> 18309419

Bifunctional organocatalyst for methanolytic desymmetrization of cyclic anhydrides: increasing enantioselectivity by catalyst dilution.

Ho Sik Rho1, Sang Ho Oh, Ji Woong Lee, Jin Yong Lee, Jik Chin, Choong Eui Song.   

Abstract

Highly enantioselective methanolysis of meso-cyclic anhydride was achieved with bifunctional organocatalyst containing a quinine-thiourea moiety; unusual concentration, temperature and solvent effects on the enantioselectivity can be explained in terms of a mechanism involving monomer-dimer equilibration of the catalyst.

Entities:  

Year:  2008        PMID： 18309419     DOI： 10.1039/b719811f

Source DB:  PubMed          Journal:  Chem Commun (Camb)        ISSN： 1359-7345            Impact factor:   6.222


  7 in total

Review 1.  Quantum mechanical investigations of organocatalysis: mechanisms, reactivities, and selectivities.

Authors:  Paul Ha-Yeon Cheong; Claude Y Legault; Joann M Um; Nihan Çelebi-Ölçüm; K N Houk
Journal:  Chem Rev       Date:  2011-06-28       Impact factor: 60.622

2.  A Theoretical Study of the Mechanism of the Desymmetrization of Cyclic meso-Anhydrides by Chiral Amino Alcohols.

Authors:  Burcu Dedeoglu; Saron Catak; K N Houk; Viktorya Aviyente
Journal:  ChemCatChem       Date:  2010-09-17       Impact factor: 5.686

3.  Synergistic organocatalysis in the kinetic resolution of secondary thiols with concomitant desymmetrization of an anhydride.

Authors:  Aldo Peschiulli; Barbara Procuranti; Cornelius J O' Connor; Stephen J Connon
Journal:  Nat Chem       Date:  2010-03-14       Impact factor: 24.427

4.  Novel bifunctional sulfonamides catalyze an enantioselective conjugate addition.

Authors:  Patrick G McGarraugh; Stacey E Brenner
Journal:  Tetrahedron       Date:  2009-01-10       Impact factor: 2.457

5.  Novel amide-functionalized chloramphenicol base bifunctional organocatalysts for enantioselective alcoholysis of meso-cyclic anhydrides.

Authors:  Lingjun Xu; Shuwen Han; Linjie Yan; Haifeng Wang; Haihui Peng; Fener Chen
Journal:  Beilstein J Org Chem       Date:  2018-01-31       Impact factor: 2.883

6.  Stereoselective Glycosylation of 2-Nitrogalactals Catalyzed by a Bifunctional Organocatalyst.

Authors:  Sandra Medina; Matthew J Harper; Edward I Balmond; Silvia Miranda; Giacomo E M Crisenza; Diane M Coe; Eoghan M McGarrigle; M Carmen Galan
Journal:  Org Lett       Date:  2016-08-16       Impact factor: 6.005

7.  Redox-configurable ambidextrous catalysis: structural and mechanistic insight.

Authors:  Shahab Mortezaei; Noelle R Catarineu; Xueyou Duan; Chunhua Hu; James W Canary
Journal:  Chem Sci       Date:  2015-07-14       Impact factor: 9.825
  7 in total

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