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Stereoelectronic Basis for the Kinetic Resolution of N‐Heterocycles with Chiral Acylating Reagents
Author(s) -
Hsieh ShengYing,
Wanner Benedikt,
Wheeler Philip,
Beauchemin André M.,
Rovis Tomislav,
Bode Jeffrey W.
Publication year - 2014
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201402818
Subject(s) - kinetic resolution , acylation , reagent , chemistry , resolution (logic) , kinetic energy , amine gas treating , combinatorial chemistry , computational chemistry , stereochemistry , organic chemistry , enantioselective synthesis , catalysis , computer science , physics , quantum mechanics , artificial intelligence
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.