Palladium-catalyzed desymmetric [2+2+2] cycloaddition of 1,6-enyne and alkyne

A novel and straightforward palladium-catalyzed desymmetric [2+2+2] cycloaddition reaction of alkyne-tethered cyclohexadienone and internal alkyne is established. Widely existing fused tricyclic hydronaphthofuran and hydronaphthopyrrole frameworks are prepared diastereoselectively in moderate to exc...

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Bibliographic Details
Published inTetrahedron Vol. 79; pp. 131862 - 131867
Main Authors Zhao, Wei-Cheng, Wang, Xin, Feng, Juhua, Tian, Ping, He, Zhi-Tao
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 22.01.2021
Elsevier
Subjects
1,6-Enyne
[2+2+2] cycloaddition
Alkyne
Chemistry
Chemistry, Organic
Palladium catalysis
Physical Sciences
Science & Technology
Tricycles
Tricycles
1,6-Enyne
Palladium catalysis
[2+2+2] cycloaddition
Alkyne
COCYCLIZATION
2,7-ALKADIYNYLIC CARBONATES
DITERPENOID ALKALOIDS
CONSTRUCTION
ARYLATIVE CYCLIZATION
ARYNES
DIYNES
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Summary:A novel and straightforward palladium-catalyzed desymmetric [2+2+2] cycloaddition reaction of alkyne-tethered cyclohexadienone and internal alkyne is established. Widely existing fused tricyclic hydronaphthofuran and hydronaphthopyrrole frameworks are prepared diastereoselectively in moderate to excellent yields. One-step aromatization process provides a new and facile access to important benzene-containing tricycles from above cycloaddition products. [Display omitted]
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2020.131862