Isothiourea-catalyzed functionalization of pyrrolyl- and indolylacetic acid: enantioselective synthesis of dihydropyridinones and one-pot synthesis of pyridinones

Shuyue Zhang, Lucas Bacheley, Claire Mary Young, Daniel Graham Stark, Timothy O'Riordan, Alexandra Martha Zoya Slawin, Andrew David Smith

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Abstract

A protocol for the isothiourea‐catalyzed enantioselective functionalization of pyrrolyl‐ and indolylacetic acids has been developed. Stereodefined dihydropyridinones are accessed through formal [4+2] cycloaddition of an in situ generated isothiouronium enolate with α,β‐unsaturated ketimines. The dihydropyridinones are obtained in moderate to excellent yield (26–97%), excellent diastereocontrol (all >95 : 5 dr) and moderate to excellent enantiocontrol (75 : 25–99 : 1 er). An unusual elimination of pyrrole or indole from the dihydropyridinone to access achiral pyridinones was observed and could be selectively promoted. A further one‐pot synthesis using an acyl imidazole was developed to give pyridinones in good to excellent yields (67–91%).
Original languageEnglish
Pages (from-to)1562-1566
Number of pages5
JournalAsian Journal of Organic Chemistry
Volume9
Issue number10
Early online date10 Jul 2020
DOIs
Publication statusPublished - Oct 2020

Keywords

  • Heterocycle synthesis
  • Organocatalysis
  • Pyrrole elimination
  • Indole elimination
  • Isothiourea

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