H-Bonding Additives Act Like Lewis.pdfVIP

ORGANIC LETTERS H-Bonding Additives Act Like Lewis 2002 Vol. 4, No. 2 Acid Catalysts 217220 Peter R. Schreiner* and Alexander Wittkopp Institut fu¨r Organische Chemie, Uniersita¨ t Go¨ ttingen, Tammannstrasse 2, 37077, Go¨ ttingen, Germany, and Department of Chemistry, Uniersity of Georgia, Athens, Georgia 30602-2556 prs@chem.uga.edu Received November 24, 2001 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. Although the use of Lewis acids is ubiquitous in organic ureas cocrystallize with oxygen-containing compounds,45,9 synthesis,1 the utilization of hydrogen-bond donor additives many form oils and make structural analyses difficult.10 in place of Lewis acids for the complexation of basic Computational studies suggested that hydrogen bond heteroatoms is rather underdeveloped.2 This kind of inter-