Photoinduced double [2 + 2] cycloaddition relay of yne–allenones for highly diastereoselective synthesis of hexacyclic 1-naphthols

文献情報

出版日 2020-08-28

DOI 10.1039/D0QO00917B

インパクトファクター 5.281

著者

Shan-Shan Zhu, Jiang-Nan Zhou, Quan-Long Wu, Wen-Juan Hao, Shu-Jiang Tu, Bo Jiang

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要旨

A new photoinduced photocatalyst-free energy-transfer strategy for double [2 + 2] cycloaddition relay of yne–allenones is reported for the first time and used to produce a series of hitherto unreported hexacyclic 1-naphthols with good yields and complete diastereoselectivity. The reaction pathway generates a class of complex three-dimensional structures with two all-carbon quaternary centers evolved from the planar conjugated system through cleavage and recombination of the C–C triple bond of yne–allenones, enabling the direct formation of four new rings in one step.

掲載誌

Organic Chemistry Frontiers

CiteScore: 7.8

自己引用率: 8.7%

年間論文数: 724

Organic Chemistry Frontiers publishes high-quality research from across organic chemistry. Emphases are placed on studies that make significant contributions to the field of organic chemistry by reporting either new or significantly improved protocols or methodologies. Topics include, but are not limited to the following: Organic synthesis Development of synthetic methodologies Catalysis Natural products Functional organic materials Supramolecular and macromolecular chemistry Physical and computational organic chemistry

Photoinduced double [2 + 2] cycloaddition relay of yne–allenones for highly diastereoselective synthesis of hexacyclic 1-naphthols

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