Photoinduced double [2 + 2] cycloaddition relay of yne–allenones for highly diastereoselective synthesis of hexacyclic 1-naphthols
Literature Information
Publication Date
2020-08-28
DOI
10.1039/D0QO00917B
Impact Factor
5.281
Authors
Shan-Shan Zhu, Jiang-Nan Zhou, Quan-Long Wu, Wen-Juan Hao, Shu-Jiang Tu, Bo Jiang
View Original
Abstract
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.
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Source Journal
Organic Chemistry Frontiers
CiteScore:
7.8
Self-citation Rate:
8.7%
Articles per Year:
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
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CAS Number:
82199-12-0
Molecular Formula:
C18H17N5O4
![(1R)-N-((1R)-1-Phenylethyl)-1-[4-(tert-butyldimethylsilyloxymethyl)cyclohexyl]ethan-1-amine structure](https://static.chemtradehub.com/structs/672/672314-45-3-47ef.webp "(1R)-N-((1R)-1-Phenylethyl)-1-[4-(tert-butyldimethylsilyloxymethyl)cyclohexyl]ethan-1-amine structure")
(1R)-N-((1R)-1-Phenylethyl)-1-[4-(tert-butyldimethylsilyloxymethyl)cyclohexyl]ethan-1-amine
CAS Number:
672314-45-3
Molecular Formula:
C23H41NOSi
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