Enantioselective Intermolecular Benzylic C-H Amination under Chiral Paddle-Wheel Diruthenium Catalysis

被引：1

作者：

Makino, Kotoko ^{[1
,2
]}

Mori, Kohei ^{[1
,2
]}

Kiryu, Shoichi ^{[1
]}

Miyazawa, Taku ^{[1
]}

Kumagai, Yuhei ^{[1
]}

Higashida, Kosuke ^{[2
]}

Kojima, Masahiro ^{[1
]}

Yoshino, Tatsuhiko ^{[2
,3
]}

Matsunaga, Shigeki ^{[1
,2
]}

机构：

[1] Hokkaido Univ, Fac Pharmaceut Sci, Sapporo 0600812, Japan

[2] Kyoto Univ, Grad Sch Sci, Kyoto 6068502, Japan

[3] Kyoto Univ, Hakubi Ctr Adv Res, Kyoto 6068502, Japan

来源：

ACS CATALYSIS | 2024年 / 15卷 / 01期

基金：

日本学术振兴会;

关键词：

Ruthenium catalysis; Asymmetric catalysis; Nitrene; C-H amination; Chemoselectivity; NITROGEN-ATOM TRANSFER; C(SP(3))-H AMINATION; DIRHODIUM TETRACARBOXYLATES; STEREOSELECTIVE-SYNTHESIS; BISMUTH-RHODIUM; BONDS; RUTHENIUM; AZIRIDINATIONS; FUNCTIONALIZATION; AMIDATION;

D O I：

10.1021/acscatal.4c06504

中图分类号：

O64 [物理化学（理论化学）、化学物理学];

学科分类号：

070304 ; 081704 ;

摘要：

A catalytic asymmetric intermolecular benzylic C-H amination was achieved under paddle-wheel diruthenium catalysis. A chiral diruthenium catalyst incorporating (S)-TPPTTL (tetraphenylphthaloyl-(S)-tert-leucine) ligand exhibited notable enantioselectivity, and aminated products were obtained with up to 99% ee. Unique chemoselectivity of the chiral diruthenium catalyst was also found for allylbenzene and alkyl-naphthalene substrates, demonstrating the complementary synthetic utility of chiral paddle-wheel Ru(II)-Ru(III) catalysts to Rh(II) counterparts.

引用

页码：523 / 528

页数：6

共 50 条

[1] Chiral paddle-wheel diruthenium complexes for asymmetric catalysis
Taku Miyazawa
Takuro Suzuki
Yuhei Kumagai
Koji Takizawa
Takashi Kikuchi
Shunsuke Kato
Akira Onoda
Takashi Hayashi
Yuji Kamei
Futa Kamiyama
Masahiro Anada
Masahiro Kojima
Tatsuhiko Yoshino
Shigeki Matsunaga
Nature Catalysis, 2020, 3 : 851 - 858
[2] Chiral paddle-wheel diruthenium complexes for asymmetric catalysis
Miyazawa, Taku
Suzuki, Takuro
Kumagai, Yuhei
Takizawa, Koji
Kikuchi, Takashi
Kato, Shunsuke
Onoda, Akira
Hayashi, Takashi
Kamei, Yuji
Kamiyama, Futa
Anada, Masahiro
Kojima, Masahiro
Yoshino, Tatsuhiko
Matsunaga, Shigeki
NATURE CATALYSIS, 2020, 3 (10) : 851 - 858
[3] Catalytic Enantioselective Amination of Enol Silyl Ethers Using a Chiral Paddle-Wheel Diruthenium Complex
Makino, Kotoko
Kumagai, Yuhei
Yoshino, Tatsuhiko
Kojima, Masahiro
Matsunaga, Shigeki
ORGANIC LETTERS, 2023, 25 (18) : 3234 - 3238
[4] Enantioselective Intermolecular C-H Amination Directed by a Chiral Cation
Fanourakis, Alexander
Williams, Benjamin D.
Paterson, Kieran J.
Phipps, Robert J.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2021, 143 (27) : 10070 - 10076
[5] Enantioselective Intermolecular Radical C-H Amination
Jin, Li-Mei
Xu, Pan
Xie, Jingjing
Zhang, X. Peter
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2020, 142 (49) : 20828 - 20836
[6] Intermolecular Enantioselective Benzylic C(sp3)-H Amination by Cationic Copper Catalysis
Dai, Ling
Chen, Ying-Ying
Xiao, Li-Jun
Zhou, Qi-Lin
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2023, 62 (24)
[7] Enantioselective, intermolecular benzylic C-H amination catalysed by an engineered iron-haem enzyme
Prier C.K.
Zhang R.K.
Buller A.R.
Brinkmann-Chen S.
Arnold F.H.
Nature Chemistry, 2017, 9 (7) : 629 - 634
[8] Enantioselective, intermolecular benzylic C-H amination catalysed by an engineered iron-haem enzyme
Prier, Christopher K.
Zhang, Ruijie K.
Buller, Andrew R.
Brinkmann-Chen, Sabine
Arnold, Frances H.
NATURE CHEMISTRY, 2017, 9 (07) : 629 - 634
[9] Enantioselective Intermolecular Radical Amidation and Amination of Benzylic C-H Bonds via Dual Copper and Photocatalysis
Chen, Xuemeng
Lian, Zhong
Kramer, Soren
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2023, 62 (13)
[10] Catalytic Enantioselective Intermolecular Benzylic C(sp3)-H Amination
Nasrallah, Ali
Boquet, Vincent
Hecker, Alexandra
Retailleau, Pascal
Darses, Benjamin
Dauban, Philippe
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2019, 58 (24) : 8192 - 8196

← 1 2 3 4 5 →