Dienolate Annulation Approach for Assembly of Densely Substituted Aromatic Architectures

Kevin A. Scott, Jeffrey R. Groch, Isaac Chogii, Michael D. Delost, Pradipta Das, Jon T. Njardarson

Research output: Contribution to journalArticlepeer-review

1 Scopus citations

Abstract

The efficient assembly of complex aromatic structures from simple acyclic building blocks is reported. An anion-cascade union of an enoate and a conjugated imine affords cyclohexenone products, which are readily aromatized to phenols. By engaging the intermediate cyclohexenones with Grignard reagents, a facile addition/elimination proceeds yielding chiral cyclohexadienes, which are then aromatized. In a complementary approach, the cyclohexenone products are converted into enol triflates, which provides a gateway to diverse aromatic architectures following cross-couplings and aromatization steps.

Original languageEnglish (US)
Pages (from-to)10555-10567
Number of pages13
JournalJournal of Organic Chemistry
Volume86
Issue number15
DOIs
StatePublished - Aug 6 2021

ASJC Scopus subject areas

  • Organic Chemistry

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