期刊
JOURNAL OF SYNTHETIC ORGANIC CHEMISTRY JAPAN
卷 73, 期 10, 页码 977-986出版社
SOC SYNTHETIC ORGANIC CHEM JPN
DOI: 10.5059/yukigoseikyokaishi.73.977
关键词
dearomaidzation; Friedel-Crafts reaction; spirocyclohexadienones; palladium; gold; allylic substitution; asymmetric catalysis
资金
- Grants-in-Aid for Scientific Research [15K07850] Funding Source: KAKEN
This review describes the development of novel dearomatization reactions of phenols using transition metal catalysis. We found that an intramolecular ipso-Friedel-Crafts allylic alkylation of phenols proceeded smoothly in the presence of Pd catalyst, producing various spiro [4.5] cyclohexadienone derivatives. The present methods could be applied to a catalytic asymmetric reaction. An asymmetric intramolecular Friedel-Crafts allylic alkylation of phenols to produce chiral 10-vinyl 9,10-dihydrophenanthrenes was also investigated. The developed process was successfully applied to the enantioselective synthesis of bioactive natural products. We also developed a novel method for synthesizing spirocycles based on a Pd-catalyzed intramolecular ipso-Friedel-Crafts alkylation of phenols to eta(3)-propargylpalladium(II) complexes. Mechanistic studies revealed that the present reaction proceeds through a rearomatization-assisited oxidative addition. An Aucatalyzed carbocyclization of phenols with a terminal alkyne via an intramolecular ipso-Friedel-Crafts alkenylation is also discussed.
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