- H-bonding additives act like Lewis acid catalysts.
H-bonding additives act like Lewis acid catalysts.
Organic letters (2002-02-14)
Peter R Schreiner, Alexander Wittkopp
PMID11796054
RÉSUMÉ
[reaction: see text] A combination of NMR, IR, and ab initio techniques reveals the striking structural similarities of an exemplary H-bonded complex of an N-acyloxazolidinone with an N,N'-disubstituted electron-poor thiourea and the corresponding Lewis acid complex. Although the H-bond association constant is lower than for the Lewis acid adduct, Diels-Alder reactions are accelerated and stereochemically altered in a fashion similar to weak Lewis acids.
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