Hydrogen bonding catalysis operates by charge stabilization in highly polar Diels-Alder reactions.
[reaction: see text] The alcohol-catalyzed Diels-Alder reactions of acrolein and benzaldehyde with Rawal's diene were evaluated with density functional theory (B3LYP/6-31G(d)). Several potential modes of catalysis with two methanol molecules were used to model catalysis by TADDOLs. In agreement with crystallographic data, cooperative catalysis with TADDOLs is predicted to be favorable.
Gordillo
Ruth
R
Department of Chemistry and Biochemistry, University of California, Los Angeles, California 90095-1569, USA.
Dudding
Travis
T
Anderson
Christopher D
CD
Houk
K N
KN
D000171:Acrolein / Q000737:chemistry*; D000438:Alcohols / Q000737:chemistry*; D001547:Benzaldehydes / Q000737:chemistry*; D002384:Catalysis; D018360:Crystallography, X-Ray; D006860:Hydrogen Bonding; D000432:Methanol / Q000737:chemistry; D008956:Models, Chemical; D008968:Molecular Conformation; D013237:Stereoisomerism
D000438:Alcohols; D001547:Benzaldehydes; D000171:Acrolein; C032175:benzaldehyde; D000432:Methanol