期刊
ORGANIC LETTERS
卷 23, 期 12, 页码 4635-4639出版社
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.1c01364
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资金
- ARC [DP180101332]
A two-step Pd-catalyzed (3 + 2) cycloaddition/HNO2 elimination reaction sequence has been developed to efficiently produce novel cyclic 1,3-dien-5-yne systems with high atom efficiency. The research allows for the selective isolation of a single diastereoisomer of the cycloadduct, demonstrating the potential for practical applications in organic synthesis.
A two-step Pd-catalyzed (3 + 2) cycloaddition/HNO2 elimination reaction sequence has been developed to give novel cyclic 1,3-dien-5-yne systems from Pd-stabilized zwitterionic 1,3-dipoles and 2-nitro-1,3-enyne substrates. The process is highly atom-efficient and tolerates the reaction of 2-vinyloxirane, 1-tosyl-2-vinylaziridine, and diethyl 2-vinylcyclopropane-1,1-dicarboxylate derived 1,3-dipoles with a variety of 2-nitro-1,3-enyne substrates. The stereochemistry of the intermediate (3 + 2) cycloadducts was determined by single crystal X-ray analysis. Furthermore, a selective kinetic elimination of the cycloadduct with an antiperiplanar relationship between the NO2 group and the participating hydrogen was demonstrated, allowing for efficient isolation of a single diastereoisomer of the cycloadduct.
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