Ru-NHC-Catalyzed Asymmetric, Complete Hydrogenation of Indoles and Benzofurans: One Catalyst with Dual Function

被引：16

作者：

Zhang, Fuhao ^{[1
]}

Sasmal, Himadri Sekhar ^{[1
]}

Daniliuc, Constantin G. G. ^{[1
]}

Glorius, Frank ^{[1
]}

机构：

[1] Westfal Wilhelms Univ Munster, Organ Chem Inst, D-48149 Munster, Germany

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2023年 / 145卷 / 29期

关键词：

N-HETEROCYCLIC CARBENES; STEREOSELECTIVE-SYNTHESIS; INHIBITOR; ACCESS; ACID; DIVERSITY; CHEMISTRY; LIGANDS; RINGS;

D O I：

10.1021/jacs.3c04983

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The highly enantioselectiveand complete hydrogenation of protectedindoles and benzofurans has been developed, affording facile accessto a range of chiral three-dimensional octahydroindoles and octahydrobenzofurans,which are prevalent in many bioactive molecules and organocatalysts.Remarkably, we are in control of the nature of the ruthenium N-heterocycliccarbene complex and employed the complex as both homogeneous and heterogeneouscatalysts, providing new avenues for its potential applications inthe asymmetric hydrogenation of more challenging aromatic compounds.

引用

页码：15695 / 15701

页数：7

共 10 条

[1] Ruthenium NHC Catalyzed Highly Asymmetric Hydrogenation of Benzofurans
Ortega, Nuria
Urban, Slawomir
Beiring, Bernhard
Glorius, Frank
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2012, 51 (07) : 1710 - 1713
[2] Ru-NHC-Catalyzed Asymmetric Hydrogenation of 2-Quinolones to Chiral 3,4-Dihydro-2-Quinolones
Hu, Tianjiao
Lueckemeier, Lukas
Daniliuc, Constantin
Glorius, Frank
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2021, 60 (43) : 23193 - 23196
[3] Highly asymmetric synthesis of (+)-corsifuran A. Elucidation of the electronic requirements in the Ruthenium-NHC catalyzed hydrogenation of benzofurans
Ortega, Nuria
Beiring, Bernhard
Urban, Slawomir
Glorius, Frank
TETRAHEDRON, 2012, 68 (26) : 5185 - 5192
[4] Ruthenium(II)-catalyzed asymmetric transfer hydrogenation of ketones using chiral oxazolinylferrocenylphosphines and one of their Ru(II) complex
Arikawa, Y
Ueoka, M
Matoba, K
Nishibayashi, Y
Hidai, M
Uemura, S
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1999, 572 (02) : 163 - 168
[5] Asymmetric Hydrogenation of Aromatic Ketones Catalyzed by L-Proline-Modified Ru-PPh3/γ-Al2O3 Catalyst
Xiong Wei
Liu Derong
Jia Yun
Qin Ruixiang
Qiu Huidong
Wang Jinbo
Li Xianjun
CHINESE JOURNAL OF CATALYSIS, 2011, 32 (07) : 1275 - 1279
[6] A practical process to chiral ferrocenyl alcohols via asymmetric transfer hydrogenation catalyzed with a PEG-bound Ru catalyst in water and its application in preparing Ugi's amine
Wu, Yinuo
Lu, Chuanjun
Shan, Wenjun
Li, Xingshu
TETRAHEDRON-ASYMMETRY, 2009, 20 (05) : 584 - 587
[7] ASYMMETRIC HYDROGENATION OF METHYL 3,5-DIOXOHEXANOATE CATALYZED BY RU-BINAP COMPLEX - A SHORT STEP ASYMMETRIC-SYNTHESIS OF DIHYDRO-6-METHYL-2H-PYRAN-2-ONE
SHAO, LM
SEKI, T
KAWANO, H
SABURI, M
TETRAHEDRON LETTERS, 1991, 32 (52) : 7699 - 7702
[8] Asymmetric hydrogenation of aromatic ketones catalyzed by (1S,2S)-DPEN-modified Ru-PPh3/γ-Al2O3 catalyst
Tang, Bo
Xiong, Wei
Liu, Ele-Rong
Jia, Yun
Wang, Jin-Bo
Chen, Hua
Li, Xian-Jun
TETRAHEDRON-ASYMMETRY, 2008, 19 (11) : 1397 - 1401
[9] Asymmetric Transfer Hydrogenation of Arylidene-Substituted Chromanones and Tetralones Catalyzed by Noyori-lkariya Ru(II) Complexes: One-Pot Reduction of C=C and C=O bonds
Caleffi, Guilherme S.
Brum, Juliana de O. C.
Costa, Angela T.
Domingos, Jorge L. O.
Costa, Paulo R. R.
JOURNAL OF ORGANIC CHEMISTRY, 2021, 86 (06): : 4849 - 4858
[10] Mechanistic Study of the Ru-Catalyzed Asymmetric Hydrogenation of Nonchelatable and Chelatable tert-Alkyl Ketones Using the Linear Tridentate sp3P/sp3NH/sp2N-Combined Ligand PN(H)N: RuNH- and RuNK-Involved Dual Catalytic Cycle
Nakane, Satoshi
Yamamura, Tomoya
Manna, Sudipta Kumar
Tanaka, Shinji
Kitamura, Masato
ACS CATALYSIS, 2018, 8 (12): : 11059 - 11075

← 1 →