PyBox–La(OTf)<sub>3</sub>-Catalyzed Enantioselective Diels–Alder Cycloadditions of 2-Alkenoylpyridines with Cyclopentadiene

Hao Wei; Yujie Zhang; Sanlin Jin; Ying Yu; Ning Chen; Jiaxi Xu; Zhanhui Yang

doi:10.3390/molecules29132978

Molecules (Jun 2024)

PyBox–La(OTf)<sub>3</sub>-Catalyzed Enantioselective Diels–Alder Cycloadditions of 2-Alkenoylpyridines with Cyclopentadiene

Hao Wei,
Yujie Zhang,
Sanlin Jin,
Ying Yu,
Ning Chen,
Jiaxi Xu,
Zhanhui Yang

Affiliations

Hao Wei: Department of Organic Chemistry, College of Chemistry, Beijing University of Chemical Technology, Beijing 100029, China
Yujie Zhang: Department of Organic Chemistry, College of Chemistry, Beijing University of Chemical Technology, Beijing 100029, China
Sanlin Jin: Department of Organic Chemistry, College of Chemistry, Beijing University of Chemical Technology, Beijing 100029, China
Ying Yu: China United Test & Certification Co., Ltd., Beijing 100088, China
Ning Chen: Department of Organic Chemistry, College of Chemistry, Beijing University of Chemical Technology, Beijing 100029, China
Jiaxi Xu: Department of Organic Chemistry, College of Chemistry, Beijing University of Chemical Technology, Beijing 100029, China
Zhanhui Yang: Department of Organic Chemistry, College of Chemistry, Beijing University of Chemical Technology, Beijing 100029, China

DOI: https://doi.org/10.3390/molecules29132978
Journal volume & issue: Vol. 29, no. 13
p. 2978

Abstract

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The PyBox–La(OTf)3-catalyzed enantioselective Diels–Alder cycloaddition of 2-alk-2-enoylpyridines with cyclopentadiene is realized, producing enantiopure disubstituted norbornenes, which possess four contiguous stereocenters and are biologically relevant structures in up to 92:8 dr and 99:1 er.

Published in Molecules

ISSN: 1420-3049 (Online)
Publisher: MDPI AG
Country of publisher: Switzerland
LCC subjects: Science: Chemistry: Organic chemistry
Website: http://www.mdpi.com/journal/molecules

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