Asymmetric Dearomatization of Naphthols via a Rh-Catalyzed C(sp2)-H Functionalization/Annulation Reaction

被引：273

作者：

Zheng, Jun ^{[1
]}

Wang, Shao-Bo ^{[1
]}

Zheng, Chao ^{[1
]}

You, Shu-Li ^{[1
]}

机构：

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

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2015年 / 137卷 / 15期

基金：

中国国家自然科学基金;

关键词：

H BOND ACTIVATION; CRAFTS ALLYLIC ALKYLATION; OXIDATIVE DEAROMATIZATION; ENANTIOSELECTIVE DEAROMATIZATION; PHENOL DEAROMATIZATION; C-C; CONSTRUCTION; ALKENES; SPIROLACTONIZATION; ANNULATION;

D O I：

10.1021/jacs.5b01707

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A Rh-catalyzed enantioselective dearomatization of 1-aryl-2-naphthols with internal alkynes via C-H functionalization reaction was achieved. In the presence of a chiral Cp/Rh catalyst and combined oxidants of Cu(OAc)(2) and air (oxygen), various highly enantioenriched spirocyclic enones bearing an all-carbon quaternary stereogenic center could be synthesized in 33-98% yields with up to 97:3 er.

引用

页码：4880 / 4883

页数：4

共 54 条

[1] Asymmetric Oxidation of o-Alkylphenols with Chiral 2-(o-Iodoxyphenyl)-oxazolines [J].

Boppisetti, Jagadish K. ;

Birman, Vladimir B. .

ORGANIC LETTERS, 2009, 11 (06) :1221-1223

[2] Rhodium Catalyzed Chelation-Assisted C-H Bond Functionalization Reactions [J].

Colby, Denise A. ;

Tsai, Andy S. ;

Bergman, Robert G. ;

Ellman, Jonathan A. .

ACCOUNTS OF CHEMICAL RESEARCH, 2012, 45 (06) :814-825

[3] A chiral hypervalent iodine(III) reagent for enantioselective dearomatization of phenols [J].

Dohi, Toshifumi ;

Maruyama, Akinobu ;

Takenaga, Naoko ;

Senami, Kento ;

Minamitsuji, Yutaka ;

Fujioka, Hiromichi ;

Caemmerer, Simon B. ;

Kita, Yasuyuki .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (20) :3787-3790

[4] Asymmetric Dearomatizing Spirolactonization of Naphthols Catalyzed by Spirobiindane-Based Chiral Hypervalent Iodine Species [J].

Dohi, Toshifumi ;

Takenaga, Naoko ;

Nakae, Tomofumi ;

Toyoda, Yosuke ;

Yamasaki, Mikio ;

Shiro, Motoo ;

Fujioka, Hiromichi ;

Maruyama, Akinobu ;

Kita, Yasuyuki .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2013, 135 (11) :4558-4566

[5] Enantioselective synthesis of bicyclo[2.2.2]octenones using a copper-mediated oxidative dearomatization/[4+2] dimerization cascade [J].

Dong, Suwei ;

Zhu, Jianglong ;

Porco, John A., Jr. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (09) :2738-+

[6] Enantioselective Palladium-Catalyzed Dearomative Cyclization for the Efficient Synthesis of Terpenes and Steroids [J].

Du, Kang ;

Guo, Pan ;

Chen, Yuan ;

Cao, Zhen ;

Wang, Zheng ;

Tang, Wenjun .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2015, 54 (10) :3033-3037

[7]

Fiege H., 2000, ULLMANS ENCY IND CHE

[8] Transition metal-catalyzed C-H activation reactions: diastereoselectivity and enantioselectivity [J].

Giri, Ramesh ;

Shi, Bing-Feng ;

Engle, Keary M. ;

Maugel, Nathan ;

Yu, Jin-Quan .

CHEMICAL SOCIETY REVIEWS, 2009, 38 (11) :3242-3272

[9] Palladium(II)-Catalyzed Oxidative Dearomatization of Free Naphthols with Two Alkyne Units [J].

Gu, Songlin ;

Luo, Lei ;

Liu, Jingjing ;

Bai, Lu ;

Zheng, Huayu ;

Wang, Yaoyu ;

Luan, Xinjun .

ORGANIC LETTERS, 2014, 16 (23) :6132-6135

[10]

Harman WD, 2004, TOP ORGANOMETAL CHEM, V7, P95

← 1 2 3 4 5 6 →