Metal-free dearomatization reactions of naphthol-ynamides for the divergent and enantioselective synthesis of azaspirocycles

Dearomatization reactions of phenols and their derivatives have evolved as efficient and practical methods for the synthesis of functionalized spirocyclic enones in the past decades. Here, an efficient metal-free intramolecular dearomatization cyclization of readily available naphthol-ynamides has b...

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Published inORGANIC CHEMISTRY FRONTIERS Vol. 9; no. 14; pp. 3709 - 3717
Main Authors Li, Hang-Hao, Zhang, Yi-Ping, Zhai, Tong-Yi, Liu, Bin-Yang, Shi, Chong-Yang, Zhou, Jin-Mei, Ye, Long-Wu
Format Journal Article
LanguageEnglish
Published CAMBRIDGE Royal Soc Chemistry 12.07.2022
Royal Society of Chemistry
Subjects
Catalysts
Chemical synthesis
Chemistry
Chemistry, Organic
Divergence
Enantiomers
Naphthol
Organic chemistry
Phenols
Physical Sciences
Science & Technology
Substrates
BRONSTED ACID
DESIGN
REAGENTS
PHENOL
CATALYTIC ASYMMETRIC DEAROMATIZATION
CONSTRUCTION
IPSO-CYCLIZATION
ACCESS
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Summary:Dearomatization reactions of phenols and their derivatives have evolved as efficient and practical methods for the synthesis of functionalized spirocyclic enones in the past decades. Here, an efficient metal-free intramolecular dearomatization cyclization of readily available naphthol-ynamides has been developed, enabling practical, atom-economical and divergent access to two azaspirocyclic compounds in mostly good to excellent yields with a wide substrate scope. Moreover, such a catalytic asymmetric dearomatization reaction has also been achieved by employing a chiral Bronsted acid as a catalyst.
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content type line 14
ISSN:2052-4129
2052-4110
2052-4110
DOI:10.1039/d2qo00685e