Organocatalytic Functionalization of Carboxylic Acids: Isothiourea-Catalyzed Asymmetric Intra- and Intermolecular Michael Addition−Lactonizations

Tetramisole promotes the catalytic asymmetric intramolecular Michael addition−lactonization of a variety of enone acids, giving carbo- and heterocyclic products with high diastereo- and enantiocontrol (up to 99:1 dr, up to 99% ee) that are readily derivatized to afford functionalized indene and dihy...

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Bibliographic Details
Published in:Journal of the American Chemical Society 2011-03, Vol.133 (8), p.2714-2720
Main Authors: Belmessieri, Dorine, Morrill, Louis C, Simal, Carmen, Slawin, Alexandra M. Z, Smith, Andrew D
Format: Article
Language:English
Subjects:
Carboxylic Acids - chemistry
Catalysis
Cyclization
Molecular Structure
Pyrones - chemical synthesis
Pyrones - chemistry
Stereoisomerism
Thiourea - analogs & derivatives
Thiourea - chemistry
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Summary:Tetramisole promotes the catalytic asymmetric intramolecular Michael addition−lactonization of a variety of enone acids, giving carbo- and heterocyclic products with high diastereo- and enantiocontrol (up to 99:1 dr, up to 99% ee) that are readily derivatized to afford functionalized indene and dihydrobenzofuran carboxylates. Chiral isothioureas also promote the catalytic asymmetric intermolecular Michael addition−lactonization of arylacetic acids and α-keto-β,γ-unsaturated esters, giving anti-dihydropyranones with high diastereo- and enantiocontrol (up to 98:2 dr, up to 99% ee).
ISSN:0002-7863
1520-5126
DOI:10.1021/ja109975c