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DABCO and DMAP—Why Are They Different in Organocatalysis?
Author(s) -
Baidya Mahiuddin,
Kobayashi Shinjiro,
Brotzel Frank,
Schmidhammer Uli,
Riedle Eberhard,
Mayr Herbert
Publication year - 2007
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.200701489
Subject(s) - dabco , octane , organocatalysis , nucleophile , chemistry , contradiction , pyridine , organic chemistry , philosophy , catalysis , epistemology , enantioselective synthesis
What makes a good organocatalyst? DABCO (1,4‐diazabicyclo[2.2.2]octane) is a thousandfold better nucleophile ( k → ) and at the same time a million times better leaving group ( k ← ) than DMAP (4‐(dimethylamino)pyridine). This apparent contradiction is resolved by consideration of the intrinsic reaction barriers.