Dienolate Annulation Approach for Assembly of Densely Substituted Aromatic Architectures

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...

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Bibliographic Details
Published in:Journal of organic chemistry Vol. 86; no. 15; pp. 10555 - 10567
Main Authors: Scott, Kevin A, Groch, Jeffrey R, Chogii, Isaac, Delost, Michael D, Das, Pradipta, Njardarson, Jon T
Format: Journal Article
Language:English
Published: American Chemical Society 06-08-2021
Online Access:Get full text
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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.
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ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.1c01211