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. 2023 Mar 17;8(12):11588-11595.
doi: 10.1021/acsomega.3c00782. eCollection 2023 Mar 28.

Catalytic Asymmetric Diels-Alder Reaction of 2'-Hydroxychalcone as a Dienophile with a VANOL-Borate Ester Complex

Xia Li  1 , Wen-Xiang Liu  2 , Cong-Cong Wang  3 , Jin-Xia Wei  4 , Yu-Qiang Wu  5 , Ze-Yun Xiao  2 , Kai Li  6 , Ya-Xiao Li  1 , Ling-Zhi Li  2
Affiliations

Catalytic Asymmetric Diels-Alder Reaction of 2'-Hydroxychalcone as a Dienophile with a VANOL-Borate Ester Complex

Xia Li et al. ACS Omega. .

Abstract

Numerous flavonoid Diels-Alder-type natural products have been isolated and received great attention from the synthetic community. Herein, we reported a catalytic strategy for an asymmetric Diels-Alder reaction of 2'-hydroxychalcone with a range of diene substrates using a chiral ligand-boron Lewis acid complex. This method enables the convenient synthesis of a wide range of cyclohexene skeletons in excellent yields with moderate to good enantioselectivities, which is critical to prepare natural product congeners for further biological studies.

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Conflict of interest statement

The authors declare no competing financial interest.

Figures

Figure 1
Figure 1
Structures of representative flavonoid Diels–Alder-type natural products derived from 2′-hydroxychalcones.
Scheme 1
Scheme 1. Diels–Alder Reaction of 2′-Hydroxychalcones
Scheme 2
Scheme 2. Diels–Alder Cycloaddition of Dienophiles and Dienes
Scheme 3
Scheme 3. Synthesis of Methylated Nicolaiodesin C
See this image and copyright information in PMC

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