Iridium-Catalyzed Intermolecular Asymmetric Dearomatization of β-Naphthols with Allyl Alcohols or Allyl Ethers

被引：100

作者：

Tu, Hang-Fei ^{[1
]}

Zheng, Chao ^{[1
]}

Xu, Ren-Qi ^{[1
]}

Liu, Xi-Jia ^{[1
]}

You, Shu-Li ^{[1
,2
]}

机构：

[1] Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Organometall Chem, 345 Lingling Lu, Shanghai 200032, Peoples R China

[2] Collaborat Innovat Ctr Chem Sci & Engn, Tianjin 300072, Peoples R China

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2017年 / 56卷 / 12期

关键词：

allylic substitution; asymmetric catalysis; dearomatization; iridium; naphthol; INTRAMOLECULAR DEAROMATIZATION; GRIGNARD-REAGENTS; ALPHA-ALLYLATION; C-C; OXIDATIVE DEAROMATIZATION; ARYLATIVE DEAROMATIZATION; PHENOL DEAROMATIZATION; SUBSTITUTION-REACTIONS; KINETIC RESOLUTION; LEAVING GROUPS;

D O I：

10.1002/anie.201609654

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

An Ir-catalyzed intermolecular asymmetric dearomatization reaction of beta-naphthols with allyl alcohols or allyl ethers was developed. When an iridium catalyst generated from [Ir(COD)Cl](2) (COD = cyclooctadiene) and a chiral P/olefin ligand is employed, highly functionalized beta-naphthalenone compounds bearing an all-carbon-substituted quaternary chiral center were obtained in up to 92% yield and 98% ee. The direct utilization of allyl alcohols as electrophiles represents an improvement from the viewpoint of atom economy. Allyl ethers were found to undergo asymmetric allylic substitution reaction under Ir catalysis for the first time. The diverse transformations of the dearomatized product to various motifs render this method attractive.

引用

页码：3237 / 3241

页数：5

共 113 条

[1]

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