Literature DB >> 23807875

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

Yuhua Zhang1, Vladimir B Birman.   

Abstract

Substitution of the tetrahydropyrimidine ring in enantioselective acyl transfer catalyst homobenzotetramisole (HBTM) 6 with methyl groups exerts a dramatic influence on its performance in the kinetic resolution of secondary alcohols. Syn-3-Methyl analogue of HBTM (9a) has proved to be superior to the parent compound in terms of catalytic activity, enantioselectivity, and synthetic accessibility.

Entities:  

Keywords:  acylation; catalyst design; kinetic resolution; organocatalysis

Year:  2009        PMID： 23807875      PMCID： PMC3691882          DOI： 10.1002/adsc.200900383

Source DB:  PubMed          Journal:  Adv Synth Catal        ISSN： 1615-4150            Impact factor:   5.837


  18 in total

1.  The direct and enantioselective, one-pot, three-component, cross-mannich reaction of aldehydes.

Authors:  Yujiro Hayashi; Wataru Tsuboi; Itaru Ashimine; Tatsuya Urushima; Mitsuru Shoji; Ken Sakai
Journal:  Angew Chem Int Ed Engl       Date:  2003-08-11       Impact factor: 15.336

2.  In search of peptide-based catalysts for asymmetric organic synthesis.

Authors:  Scott J Miller
Journal:  Acc Chem Res       Date:  2004-08       Impact factor: 22.384

3.  Enantioselective acylation of secondary alcohols catalyzed by chiral N-heterocyclic carbenes.

Authors:  Taichi Kano; Kouji Sasaki; Keiji Maruoka
Journal:  Org Lett       Date:  2005-03-31       Impact factor: 6.005

4.  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

5.  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

6.  Benzotetramisole: a remarkably enantioselective acyl transfer catalyst.

Authors:  Vladimir B Birman; Ximin Li
Journal:  Org Lett       Date:  2006-03-30       Impact factor: 6.005

7.  Asymmetric synthesis of beta-substituted alpha-methyl-beta-amino esters by Mannich reaction of (S,S)-(+)-pseudoephedrine acetamide derived enolate with imines.

Authors:  J L Vicario; D Badía; L Carrillo
Journal:  Org Lett       Date:  2001-03-08       Impact factor: 6.005

8.  Asymmetric catalysis with "planar-chiral" derivatives of 4-(dimethylamino)pyridine.

Authors:  Gregory C Fu
Journal:  Acc Chem Res       Date:  2004-08       Impact factor: 22.384

9.  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

10.  Concise synthesis of spirocyclic, bridged gamma-butyrolactones via stereospecific, dyotropic rearrangements of beta-lactones involving 1,2-acyl and delta-lactone migrations.

Authors:  Vikram C Purohit; Andrea S Matla; Daniel Romo
Journal:  J Am Chem Soc       Date:  2008-07-16       Impact factor: 15.419
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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

2.  Determination of absolute configuration using kinetic resolution catalysts.

Authors:  Alexander J Wagner; Jonathan G David; Scott D Rychnovsky
Journal:  Org Lett       Date:  2011-07-21       Impact factor: 6.005

3.  Determination of absolute configuration of secondary alcohols using thin-layer chromatography.

Authors:  Alexander J Wagner; Scott D Rychnovsky
Journal:  J Org Chem       Date:  2013-04-17       Impact factor: 4.354

4.  Benzotetramisole-catalyzed dynamic kinetic resolution of azlactones.

Authors:  Xing Yang; Guojian Lu; Vladimir B Birman
Journal:  Org Lett       Date:  2010-02-19       Impact factor: 6.005

5.  Isothiourea-catalysed enantioselective pyrrolizine synthesis: synthetic and computational studies.

Authors:  Daniel G Stark; Patrick Williamson; Emma R Gayner; Stefania F Musolino; Ryan W F Kerr; James E Taylor; Alexandra M Z Slawin; Timothy J C O'Riordan; Stuart A Macgregor; Andrew D Smith
Journal:  Org Biomol Chem       Date:  2016-08-04       Impact factor: 3.876

6.  6-exo-trig Michael addition-lactonizations for catalytic enantioselective chromenone synthesis.

Authors:  Rifahath M Neyyappadath; David B Cordes; Alexandra M Z Slawin; Andrew D Smith
Journal:  Chem Commun (Camb)       Date:  2017-02-23       Impact factor: 6.222

7.  Isothiourea-Catalysed Acylative Kinetic Resolution of Aryl-Alkenyl (sp2 vs. sp2 ) Substituted Secondary Alcohols.

Authors:  Stefania F Musolino; O Stephen Ojo; Nicholas J Westwood; James E Taylor; Andrew D Smith
Journal:  Chemistry       Date:  2016-11-30       Impact factor: 5.236

8.  Isothiourea-Catalyzed Acylative Kinetic Resolution of Tertiary α-Hydroxy Esters.

Authors:  Shen Qu; Samuel M Smith; Víctor Laina-Martín; Rifahath M Neyyappadath; Mark D Greenhalgh; Andrew D Smith
Journal:  Angew Chem Int Ed Engl       Date:  2020-07-16       Impact factor: 15.336

9.  Non-bonding 1,5-S···O interactions govern chemo- and enantioselectivity in isothiourea-catalyzed annulations of benzazoles.

Authors:  Emily R T Robinson; Daniel M Walden; Charlene Fallan; Mark D Greenhalgh; Paul Ha-Yeon Cheong; Andrew D Smith
Journal:  Chem Sci       Date:  2016-07-04       Impact factor: 9.825
  9 in total

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