The photo-Nazarov reaction: scope and application

Autor:	Yingbo Shi, Shujun Cai, Shuanhu Gao, Zheming Xiao
Rok vydání:	2014
Předmět:	Reaction conditions chemistry.chemical_compound chemistry Pyran Aryl Organic Chemistry Organic chemistry Aromaticity General Chemistry Enone Catalysis
Zdroj:	Chemistry (Weinheim an der Bergstrasse, Germany). 20(28)
ISSN:	1521-3765
Popis:	The reaction conditions and scope of the photo-Nazarov reaction of aryl vinyl ketones were investigated. In contrast to the conventional acid-catalyzed methods, this photolytic electrocyclization proceeds in the neutral or basic conditions. Irradiating substrates bearing various aromatic rings, acid-sensitive groups, cyclohexenyl, cycloheptenyl, and unsaturated pyran with UV-light (254 nm) smoothly yielded hexahydrofluorenones and related structures. This photo-Nazarov reaction could also be applicable to the substrates carrying β-alkyl groups on the enone, which gave corresponding polycyclic rings containing quaternary centers. These photo-electrocyclized products may prove useful for synthesizing a variety of natural products and their derivatives. Further application of this mild photo-Nazarov reaction in the synthesis of taiwaniaquinol B was achieved.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_dedup___::96fa48521aa0ee264e09d1d84d6cb98f https://pubmed.ncbi.nlm.nih.gov/24920398 Zobrazit plný text záznamu Plný text ve formátu PDF Plný text ve formátu HTML
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