Literature DB >> 20099896

Benzotetramisole-catalyzed dynamic kinetic resolution of azlactones.

Xing Yang1, Guojian Lu, Vladimir B Birman.   

Abstract

Enantioselective acyl transfer catalyst benzotetramisole (BTM) has been found to promote dynamic kinetic resolution of azlactones providing di(1-naphthyl)methyl esters of alpha-amino acids with up to 96% ee.

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Year:  2010        PMID： 20099896      PMCID： PMC3947837          DOI： 10.1021/ol902969j

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


  14 in total

1.  Homobenzotetramisole-Catalyzed Kinetic Resolution of alpha-Aryl-, alpha-Aryloxy-, and alpha-Arylthioalkanoic Acids.

Authors:  Xing Yang; Vladimir B Birman
Journal:  Adv Synth Catal       Date:  2009       Impact factor: 5.837

2.  Highly efficient dynamic kinetic resolution of azlactones by urea-based bifunctional organocatalysts.

Authors:  Albrecht Berkessel; Felix Cleemann; Santanu Mukherjee; Thomas N Müller; Johann Lex
Journal:  Angew Chem Int Ed Engl       Date:  2005-01-21       Impact factor: 15.336

3.  Kinetic resolution of 2-oxazolidinones via catalytic, enantioselective N-acylation.

Authors:  Vladimir B Birman; Hui Jiang; Ximin Li; Lei Guo; Eric W Uffman
Journal:  J Am Chem Soc       Date:  2006-05-24       Impact factor: 15.419

Review 4.  The diverse chemistry of oxazol-5-(4H)-ones.

Authors:  Jason S Fisk; Robert A Mosey; Jetze J Tepe
Journal:  Chem Soc Rev       Date:  2007-03-12       Impact factor: 54.564

5.  Effects of Methyl Substituents on the Activity and Enantioselectivity of Homobenzotetramisole-Based Catalysts in the Kinetic Resolution of Alcohols.

Authors:  Yuhua Zhang; Vladimir B Birman
Journal:  Adv Synth Catal       Date:  2009-10-01       Impact factor: 5.837

6.  Asymmetric synthesis of protected arylglycines by rhodium-catalyzed addition of arylboronic acids to N-tert-butanesulfinyl imino esters.

Authors:  Melissa A Beenen; Daniel J Weix; Jonathan A Ellman
Journal:  J Am Chem Soc       Date:  2006-05-17       Impact factor: 15.419

7.  Second-generation organocatalysts for the highly enantioselective dynamic kinetic resolution of azlactones.

Authors:  Albrecht Berkessel; Santanu Mukherjee; Felix Cleemann; Thomas N Muller; Johann Lex
Journal:  Chem Commun (Camb)       Date:  2005-02-15       Impact factor: 6.222

8.  Kinetic resolution of propargylic alcohols catalyzed by benzotetramisole.

Authors:  Vladimir B Birman; Lei Guo
Journal:  Org Lett       Date:  2006-10-12       Impact factor: 6.005

9.  Structural optimization of thiourea-based bifunctional organocatalysts for the highly enantioselective dynamic kinetic resolution of azlactones.

Authors:  Albrecht Berkessel; Santanu Mukherjee; Thomas N Müller; Felix Cleemann; Katrin Roland; Marc Brandenburg; Jörg-M Neudörfl; Johann Lex
Journal:  Org Biomol Chem       Date:  2006-11-01       Impact factor: 3.876

10.  Homobenzotetramisole: an effective catalyst for kinetic resolution of aryl-cycloalkanols.

Authors:  Vladimir B Birman; Ximin Li
Journal:  Org Lett       Date:  2008-02-16       Impact factor: 6.005
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  9 in total

1.  Kinetic resolution of secondary alcohols using amidine-based catalysts.

Authors:  Ximin Li; Hui Jiang; Eric W Uffman; Lei Guo; Yuhua Zhang; Xing Yang; Vladimir B Birman
Journal:  J Org Chem       Date:  2012-02-09       Impact factor: 4.354

Review 2.  The Cation-π Interaction in Small-Molecule Catalysis.

Authors:  C Rose Kennedy; Song Lin; Eric N Jacobsen
Journal:  Angew Chem Int Ed Engl       Date:  2016-06-22       Impact factor: 15.336

3.  Chiral Brønsted Acid Catalyzed Kinetic Resolutions.

Authors:  Kimberly S Petersen
Journal:  Asian J Org Chem       Date:  2016-03-07       Impact factor: 3.319

4.  Traversing Steric Limitations by Cooperative Lewis Base/Palladium Catalysis: An Enantioselective Synthesis of α-Branched Esters Using 2-Substituted Allyl Electrophiles.

Authors:  Kevin J Schwarz; Colin M Pearson; Gabriel A Cintron-Rosado; Peng Liu; Thomas N Snaddon
Journal:  Angew Chem Int Ed Engl       Date:  2018-05-18       Impact factor: 15.336

5.  Enantioselective α-Benzylation of Acyclic Esters Using π-Extended Electrophiles.

Authors:  Kevin J Schwarz; Chao Yang; James W B Fyfe; Thomas N Snaddon
Journal:  Angew Chem Int Ed Engl       Date:  2018-08-20       Impact factor: 15.336

6.  Asymmetric Isothiourea-Catalysed Formal [3+2] Cycloadditions of Ammonium Enolates with Oxaziridines.

Authors:  Siobhan R Smith; Charlene Fallan; James E Taylor; Ross McLennan; David S B Daniels; Louis C Morrill; Alexandra M Z Slawin; Andrew D Smith
Journal:  Chemistry       Date:  2015-06-12       Impact factor: 5.236

7.  Multiple roles of aryloxide leaving groups in enantioselective annulations employing α,β-unsaturated acyl ammonium catalysis.

Authors:  Mark D Greenhalgh; Shen Qu; Alexandra M Z Slawin; Andrew D Smith
Journal:  Chem Sci       Date:  2018-05-04       Impact factor: 9.825

8.  Theoretical Study on the Epimerization of Azlactone Rings: Keto-Enol Tautomerism or Base-Mediated Racemization?

Authors:  Pedro P de Castro; Gabriel M F Batista; Hélio F Dos Santos; Giovanni W Amarante
Journal:  ACS Omega       Date:  2018-03-26

9.  Recyclable and Stable α-Methylproline-Derived Chiral Ligands for the Chemical Dynamic Kinetic Resolution of free C,N-Unprotected α-Amino Acids.

Authors:  Shuangjie Shu; Liang Zhao; Shengbin Zhou; Chenglin Wu; Hong Liu; Jiang Wang
Journal:  Molecules       Date:  2019-06-13       Impact factor: 4.411
  9 in total

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