Organocatalytic functionalization of carboxylic acids: isothiourea-catalyzed asymmetric intra- and intermolecular Michael Addition−lactonizations

Belmessieri, Dorine, Morrill, Louis ORCID: https://orcid.org/0000-0002-6453-7531, Simal, Carmen, Slawin, Alexandra M. Z. and Smith, Andrew D. 2011. Organocatalytic functionalization of carboxylic acids: isothiourea-catalyzed asymmetric intra- and intermolecular Michael Addition−lactonizations. Journal of the American Chemical Society 133 (8) , pp. 2714-2720. 10.1021/ja109975c

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Abstract

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).

Item Type:	Article
Date Type:	Publication
Status:	Published
Schools:	Schools > Chemistry
Subjects:	Q Science > QD Chemistry
Publisher:	American Chemical Society
ISSN:	0002-7863
Last Modified:	28 Oct 2022 09:22
URI:	https://orca.cardiff.ac.uk/id/eprint/74299

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