Sc(OTf)3 Catalyzed [4+2]-Annulation Reaction between Electron-Rich Phenols and Donor-Acceptor Cyclopropanes: Synthesis of Polysubstituted Dihydronaphthols

被引：26
作者：
Luo, Yong-Chun [1 ]
Ma, He [1 ]
Hu, Xiu-Qin [1 ]
Xu, Peng-Fei [1 ]
机构：
[1] Lanzhou Univ, State Key Lab Appl Organ Chem, Coll Chem & Chem Engn, Lanzhou 730000, Gansu, Peoples R China
来源：
JOURNAL OF ORGANIC CHEMISTRY | 2017年 / 82卷 / 02期
关键词：
DOUBLY ACTIVATED CYCLOPROPANES; RING-OPENING CYCLIZATIONS; LEWIS-ACID; ASYMMETRIC-SYNTHESIS; BIOMIMETIC SYNTHESIS; CYCLOADDITION; ANNULATION; 1,1-DIESTERS; TETRAHYDROCARBAZOLES; ALKYLATION;
D O I：
10.1021/acs.joc.6b02566
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
On the basis of the Lewis acid-catalyzed Friedel Crafts alkylation between 1-aryl-2-arylcyclopropanecarboxylate esters and electron-rich phenols, a Sc(OTf)(3) catalyzed cascade [4 + 2]-annulation reaction was developed for the direct synthesis of polysubstituted dihydronaphthols from phenols. In this reaction, the structure of products is dominated by the directing effect of the substituent groups on phenols. Meanwhile, a one-pot Friedel-Crafts alkylation/oxidative cyclization reaction was also developed for the synthesis of spiro-fused 2,5-cyclohexadienones.
引用
收藏
页码：1013 / 1023
页数：11
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