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. 2022 Jan 21;24(2):762-766.
doi: 10.1021/acs.orglett.1c04266. Epub 2022 Jan 10.

Atroposelective Desymmetrization of Resorcinol-Bearing Quinazolinones via Cu-Catalyzed C-O Bond Formation

Hyung Yoon  1 , Alexandra Galls  1 , Soren D Rozema  1 , Scott J Miller  1
Affiliations

Atroposelective Desymmetrization of Resorcinol-Bearing Quinazolinones via Cu-Catalyzed C-O Bond Formation

Hyung Yoon et al. Org Lett. .

Abstract

Enantioselective Cu-catalyzed C-O cross coupling reactions yielding atropisomeric resorcinol-bearing quinazolinones have been developed. Utilizing a new guanidinylated dimeric peptidic ligand, a set of products were generated in good yields with excellent stereocontrol. The transformation was readily scalable, and a range of product derivatizations were performed.

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Conflict of interest statement

The authors declare no competing financial interests.

Figures

Figure 1.
Figure 1.
Overview of Bioactive Molecules and Enantioselective Cu-Catalyzed Ullman Coupling
Figure 2.
Figure 2.
Cu-Catalyzed C–O Cross Coupling of Quinazolinone: Initial Hit
Figure 3.
Figure 3.. Cu-Catalyzed C–O Cross Coupling: Substrate Scopea
a Reactions run on 0.2 mmol scale. Isolated yields.
Figure 4.
Figure 4.. Derivatization of Quinazolinone 3aa
a Reactions run on 0.1 mmol scale. Isolated yields.
Figure 5.
Figure 5.
Postulated Mechanism for the Cu-Catalyzed C–O Cross Coupling
See this image and copyright information in PMC

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