Enantioselective [3 + 2] Cycloaddition of Vinylcyclopropanes with Alkenyl N-Heteroarenes Enabled by Palladium Catalysis

Wen-Dao Chu; Ya-Ting Wang; Tian-Tian Liang; Teng Long; Jia-Yu Zuo; Zhihui Shao; Bo Chen; Cheng-Yu He; Quan-Zhong Liu

doi:10.1021/acs.orglett.2c01326

Enantioselective [3 + 2] Cycloaddition of Vinylcyclopropanes with Alkenyl N-Heteroarenes Enabled by Palladium Catalysis

Org Lett. 2022 Jun 10;24(22):3965-3969. doi: 10.1021/acs.orglett.2c01326. Epub 2022 May 31.

Authors

Wen-Dao Chu^{1

2}, Ya-Ting Wang¹, Tian-Tian Liang¹, Teng Long¹, Jia-Yu Zuo¹, Zhihui Shao², Bo Chen¹, Cheng-Yu He¹, Quan-Zhong Liu¹

Affiliations

¹ Chemical Synthesis and Pollution Control Key Laboratory of Sichuan Province, College of Chemistry and Chemical Engineering, China West Normal University, No. 1, Shida Road, Nanchong 637002, P.R. China.
² Key Laboratory of Medicinal Chemistry for Natural Resource, Ministry of Education, School of Chemical Science and Technology, Yunnan Provincial Center for Research & Development of Natural Products, State Key Laboratory for Conservation and Utilization of Bio-Resources in Yunnan, Yunnan University, Kunming 650091, P.R. China.

PMID: 35639837
DOI: 10.1021/acs.orglett.2c01326

Abstract

The first catalytic enantioselective [3 + 2] cycloaddition reaction between vinylcyclopropanes and alkenyl N-heteroarenes in the presence of LiBr and a Pd(0)/SEGPHOS complex was developed. LiBr plays a key role in improving the reactivity of alkenyl N-heteroarenes as a mild Lewis acid.