Dienolate Annulation Approach for Assembly of Densely Substituted Aromatic Architectures

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 reagent...

Full description

Saved in:
Bibliographic Details
Published in:Journal of organic chemistry 2021-08, Vol.86 (15), p.10555-10567
Main Authors: Scott, Kevin A, Groch, Jeffrey R, Chogii, Isaac, Delost, Michael D, Das, Pradipta, Njardarson, Jon T
Format: Article
Language:English
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary: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.
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.1c01211