Journal
TETRAHEDRON
Volume 62, Issue 2-3, Pages 302-310Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2005.09.071
Keywords
asymmetric acylation; chiral N-heterocyclic carbene; imidazolium; kinetic resolution
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Chiral N-heterocyclic carbenes are generated from C-2-symmetric 1,3-bis(1-arylethyl)imidazolium salts and potassium tert-butoxide. These C2-symmetric imidazolidenyl carbenes catalyze enantioselective acylation of racemic secondary alcohols. The asymmetric acylation of 1-(1-naphthyl)ethanol was achieved in up to 68% cc of the acylated product, using (R,R)-1,3-bis[(1-naphthyl)ethyl]imidazolium tetrafluoroborate as a precursor of the chiral N-heterocyclic carbene and vinyl propionate as the acyl donor. (c) 2005 Elsevier Ltd. All rights reserved.
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