Literature DB >> 24839065

Stereoelectronic basis for the kinetic resolution of N-heterocycles with chiral acylating reagents.

Sheng-Ying Hsieh1, Benedikt Wanner, Philip Wheeler, André M Beauchemin, Tomislav Rovis, Jeffrey W Bode.   

Abstract

The kinetic resolution of N-heterocycles with chiral acylating agents reveals a previously unrecognized stereoelectronic effect in amine acylation. Combined with a new achiral hydroxamate, this effect makes possible the resolution of various N-heterocycles by using easily prepared reagents. A transition-state model to rationalize the stereochemical outcome of this kinetic resolution is also proposed.
© 2014 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  N-heterocycles; hydroxamic acid; kinetic resolution; stereoelectronic effects; synthetic methods

Mesh：

Year:  2014        PMID： 24839065      PMCID： PMC4125202          DOI： 10.1002/chem.201402818

Source DB:  PubMed          Journal:  Chemistry        ISSN： 0947-6539            Impact factor:   5.236


  25 in total

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2.  Kinetic resolution of amines: a highly enantioselective and chemoselective acetylating agent with a unique solvent-induced reversal of stereoselectivity.

Authors:  Stellios Arseniyadis; Alain Valleix; Alain Wagner; Charles Mioskowski
Journal:  Angew Chem Int Ed Engl       Date:  2004-06-21       Impact factor: 15.336

3.  Tuning the enantioselective N-acetylation of racemic amines: a spectacular salt effect.

Authors:  Stellios Arseniyadis; Pithani V Subhash; Alain Valleix; Suju P Mathew; Donna G Blackmond; Alain Wagner; Charles Mioskowski
Journal:  J Am Chem Soc       Date:  2005-05-04       Impact factor: 15.419

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 resolutions of indolines by a nonenzymatic acylation catalyst.

Authors:  Forrest O Arp; Gregory C Fu
Journal:  J Am Chem Soc       Date:  2006-11-08       Impact factor: 15.419

6.  Catalytic kinetic resolution of cyclic secondary amines.

Authors:  Michael Binanzer; Sheng-Ying Hsieh; Jeffrey W Bode
Journal:  J Am Chem Soc       Date:  2011-11-18       Impact factor: 15.419

7.  Merging nucleophilic and hydrogen bonding catalysis: an anion binding approach to the kinetic resolution of propargylic amines.

Authors:  Eric G Klauber; Chandra Kanta De; Tejas K Shah; Daniel Seidel
Journal:  J Am Chem Soc       Date:  2010-10-06       Impact factor: 15.419

8.  Covalent modification of subtilisin Bacillus lentus cysteine mutants with enantiomerically pure chiral auxiliaries causes remarkable changes in activity.

Authors:  M Dickman; J B Jones
Journal:  Bioorg Med Chem       Date:  2000-08       Impact factor: 3.641

9.  Peptide-catalyzed kinetic resolution of formamides and thioformamides as an entry to nonracemic amines.

Authors:  Brandon S Fowler; Peter J Mikochik; Scott J Miller
Journal:  J Am Chem Soc       Date:  2010-03-10       Impact factor: 15.419

10.  Enantioselective benzoylation of alpha-amino esters using (S)-1-benzoyl-2- (alpha-acetoxyethyl)benzimidazole, a chiral benzimidazolide.

Authors:  Anil V Karnik; Suchitra S Kamath
Journal:  J Org Chem       Date:  2007-08-22       Impact factor: 4.354
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  1 in total

1.  Catalytic Kinetic Resolution of Disubstituted Piperidines by Enantioselective Acylation: Synthetic Utility and Mechanistic Insights.

Authors:  Benedikt Wanner; Imants Kreituss; Osvaldo Gutierrez; Marisa C Kozlowski; Jeffrey W Bode
Journal:  J Am Chem Soc       Date:  2015-08-26       Impact factor: 15.419
  1 in total

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