H-Bonding Additives Act Like Lewis Acid Catalysts
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- 1 January 2002
- journal article
- letter
- Published by American Chemical Society (ACS) in Organic Letters
- Vol. 4 (2) , 217-220
- https://doi.org/10.1021/ol017117s
Abstract
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.Keywords
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