Catalytic enantioselective C(sp3)-H functionalization: intramolecular benzylic [1,5]-hydride shift

被引：30

作者：

Yu, Jie ^{[1
]}

Li, Nan ^{[2
]}

Chen, Dian-Feng ^{[2
]}

Luo, Shi-Wei ^{[2
]}

机构：

[1] Anhui Agr Univ, Dept Appl Chem, Hefei 230036, Peoples R China

[2] Univ Sci & Technol China, Dept Chem, Hefei 230026, Peoples R China

来源：

TETRAHEDRON LETTERS | 2014年 / 55卷 / 17期

基金：

中国博士后科学基金;

关键词：

Asymmetric catalysis; 1,5]-Hydride transfer; Benzylic C(sp(3))-H bond; Side-armed bisoxazoline; C-H BOND; CHIRAL BIS(OXAZOLINE) LIGANDS; OXAZOLINE-CONTAINING LIGANDS; RING-CLOSURE REACTIONS; ASYMMETRIC CATALYSIS; ALKYNYL ETHERS; COMPLEXES; CYCLOPROPANATION; HYDROALKYLATION; COUNTERANIONS;

D O I：

10.1016/j.tetlet.2014.03.089

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The catalytic asymmetric [1,5]-hydride transfer/cyclization sequence involving benzylic C(sp(3))-H bond was established, providing tetrahydronaphthalene derivatives in moderate to high yield with up to 69% ee, by employing the copper complex of side-armed bisoxazoline as chiral catalyst. (C) 2014 Elsevier Ltd. All rights reserved.

引用

页码：2859 / 2864

页数：6

共 50 条

[41] Enantioselective C(sp3)-H bond activation by chiral transition metal catalysts [J].

Saint-Denis, Tyler G. ;

Zhu, Ru-Yi ;

Chen, Gang ;

Wu, Qing-Feng ;

Yu, Jin-Quan .

SCIENCE, 2018, 359 (6377) :759-+

[42] Chiral Iron Porphyrins Catalyze Enantioselective Intramolecular C(sp3)-H Bond Amination Upon Visible-Light Irradiation [J].

Wang, Hua-Hua ;

Shao, Hui ;

Huang, Guanglong ;

Fan, Jianqiang ;

To, Wai-Pong ;

Dang, Li ;

Liu, Yungen ;

Che, Chi-Ming .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2023, 62 (19)

[43] Catalytic C(sp3)-H Alkylation via an Iron Carbene Intermediate [J].

Griffin, Jennifer R. ;

Wendell, Chloe I. ;

Garwin, Jacob A. ;

White, M. Christina .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2017, 139 (39) :13624-13627

[44] A chiral porous organic polymer as a heterogeneous ligand for enantioselective Pd-catalyzed C(sp3)-H functionalization [J].

Bennedsen, Niklas Rosendal ;

Kramer, Soren ;

Kegnaes, Soren .

CATALYSIS SCIENCE & TECHNOLOGY, 2020, 10 (22) :7697-7705

[45] Catalytic Functionalization of Methyl Group on Silicon: Iridium-Catalyzed C(sp3)-H Borylation of Methylchlorosilanes [J].

Ohmura, Toshimichi ;

Torigoe, Takeru ;

Suginome, Michinori .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2012, 134 (42) :17416-17419

[46] Enantioselective C(sp3)-H Amidation of Thioamides Catalyzed by a CobaltIII/Chiral Carboxylic Acid Hybrid System [J].

Fukagawa, Seiya ;

Kato, Yoshimi ;

Tanaka, Ryo ;

Kojima, Masahiro ;

Yoshino, Tatsuhiko ;

Matsunaga, Shigeki .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2019, 58 (04) :1153-1157

[47] Expeditious Construction of a Carbobicyclic Skeleton via sp3-C-H Functionalization: Hydride Shift from an Aliphatic Tertiary Position in an Internal Redox Process [J].

Mori, Keiji ;

Sueoka, Shosaku ;

Akiyama, Takahiko .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2011, 133 (08) :2424-2426

[48] An addition of benzylic sp3 C-H to electron-deficient olefins [J].

Li, Hong-Ying ;

Xing, Li-Juan ;

Xu, Tong ;

Wang, Peng ;

Liu, Rui-Hua ;

Wang, Bin .

TETRAHEDRON LETTERS, 2013, 54 (08) :858-860

[49] Iron-Catalyzed C(sp3)-C(sp3) Bond Formation through C(sp3)-H Functionalization: A Cross-Coupling Reaction of Alcohols with Alkenes [J].

Zhang, Shu-Yu ;

Tu, Yong-Qiang ;

Fan, Chun-An ;

Zhang, Fu-Min ;

Shi, Lei .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (46) :8761-8765

[50] Enantioselective Copper-Catalyzed Cyanation of Remote C(sp3)-H Bonds Enabled by 1,5-Hydrogen Atom Transfer [J].

Wang, Cheng-Yu ;

Qin, Zi-Yang ;

Huang, Yu-Ling ;

Jin, Ruo-Xing ;

Lan, Quan ;

Wang, Xi-Sheng .

ISCIENCE, 2019, 21 :490-+

← 1 2 3 4 5 →