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Hydrogen bonding catalysis operates by charge stabilization in highly polar Diels-Alder reactions.

ABSTRACT: [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.

SUBMITTER: Gordillo R

PROVIDER: S-EPMC2531143 | biostudies-literature | 2007 Feb

REPOSITORIES: biostudies-literature

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Hydrogen bonding catalysis operates by charge stabilization in highly polar Diels-Alder reactions.

Gordillo Ruth R Dudding Travis T Anderson Christopher D CD Houk K N KN

Organic letters 20070201 3

[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. ...[more]

PMID: 17249797

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