Literature DB >> 15853296

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

Stellios Arseniyadis1, Pithani V Subhash, Alain Valleix, Suju P Mathew, Donna G Blackmond, Alain Wagner, Charles Mioskowski.   

Abstract

We have described a spectacular salt effect in the kinetic resolution of (+/-)-1-phenylethylamine, which leads to an increase in reactivity, high levels of selectivity, and a complete reversal of the stereoselectivity. By tuning the reaction conditions, we were able to increase the selectivity factor of (1S,2S)-1 to s = 115.

Entities:  

Year:  2005        PMID: 15853296     DOI: 10.1021/ja051302+

Source DB:  PubMed          Journal:  J Am Chem Soc        ISSN: 0002-7863            Impact factor:   15.419


  3 in total

1.  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

2.  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

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

Authors:  Sheng-Ying Hsieh; Benedikt Wanner; Philip Wheeler; André M Beauchemin; Tomislav Rovis; Jeffrey W Bode
Journal:  Chemistry       Date:  2014-05-18       Impact factor: 5.236

  3 in total

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