Copper-Catalyzed Asymmetric Reductions of Aryl/Heteroaryl Ketones under Mild Aqueous Micellar Conditions

被引：11

作者：

Fialho, David M. ^{[1
]}

Etemadi-Davan, Elham ^{[1
]}

Langner, Olivia C. ^{[1
]}

Takale, Balaram S. ^{[1
]}

Gadakh, Amol ^{[2
]}

Sambasivam, Ganesh ^{[2
]}

Lipshutz, Bruce H. ^{[1
]}

机构：

[1] Univ Calif Santa Barbara, Dept Chem & Biochem, Santa Barbara, CA 93106 USA

[2] Anthem Biosci Private Ltd, Bangalore 560099, Karnataka, India

来源：

ORGANIC LETTERS | 2021年 / 23卷 / 09期

关键词：

HYDROGEN-TRANSFER REDUCTION; AROMATIC KETONES; AMINO KETONES; HYDROSILYLATION; EFFICIENT; ARYL; APREPITANT; ISOMERS; LIGANDS; COMPLEX;

D O I：

10.1021/acs.orglett.1c00746

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Enantioselective syntheses of nonracemic secondary alcohols have been achieved in an aqueous micellar medium via copper-catalyzed (Cu(OAc)(2)center dot H2O/(R)-3,4,5-MeO- MeO-BI-PHEP) reduction of aryl/heteroaryl ketones. This methodology serves as a green protocol to access enantio-enriched alcohols under mild conditions (0-22 degrees C) using a base metal catalyst, together with an inexpensive, innocuous, and convenient stoichiometric hydride source (PMHS). The secondary alcohol products are formed in good to excellent yields with ee values greater than 90%.

引用

页码：3282 / 3286

页数：5

共 50 条

[1] Copper-Catalyzed Asymmetric Hydrogenation of Aryl and Heteroaryl Ketones
Krabbe, Scott W.
Hatcher, Mark A.
Bowman, Roy K.
Mitchell, Mark B.
McClure, Michael S.
Johnson, Jeffrey S.
[J]. ORGANIC LETTERS, 2013, 15 (17) : 4560 - 4563
[2] Copper-Catalyzed Amination of Aryl Halides with Aqueous Ammonia under Mild Conditions
Quan, Zhengjun
Xia, Haidong
Zhang, Zhang
Da, Yuxia
Wang, Xicun
[J]. CHINESE JOURNAL OF CHEMISTRY, 2013, 31 (04) : 501 - 506
[3] Copper-Catalyzed Asymmetric Hydrosilylation of β-Nitroethyl Aryl Ketones
Zeng, Weijun
Tan, Xuefeng
Yu, Yang
Chen, Gen-Qiang
Zhang, Xumu
[J]. ORGANIC LETTERS, 2020, 22 (03) : 858 - 862
[4] Copper-Catalyzed Amination of Aryl Chlorides under Mild Reaction Conditions
Ai, Han-Jun
Kim, Seoung-Tae
Liu, Cecilia
Buchwald, Stephen L.
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2024, 146 (38) : 25949 - 25955
[5] Copper-Catalyzed Hydroxylation of (Hetero)aryl Halides under Mild Conditions
Xia, Shanghua
Gan, Lu
Wang, Kaihang
Li, Zheng
Ma, Dawei
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2016, 138 (41) : 13493 - 13496
[6] Copper-Catalyzed Amination of Aryl Chlorides under Mild Reaction Conditions
Ai, Han-Jun
Kim, Seoung-Tae
Liu, Cecilia
Buchwald, Stephen L.
[J]. Journal of the American Chemical Society, 2024,
[7] Low Catalyst Loadings for Copper-Catalyzed O-Arylation of Phenols with Aryl and Heteroaryl Halides under Mild Conditions
Yong, Fui-Fong
Teo, Yong-Chua
Yan, Yaw-Kai
Chua, Guan-Leong
[J]. SYNLETT, 2012, 23 (01) : 101 - 106
[8] Efficient copper-catalyzed amination of DNA-conjugated aryl iodides under mild aqueous conditions
Ruff, Yves
Berst, Frederic
[J]. MEDCHEMCOMM, 2018, 9 (07) : 1188 - 1193
[9] Copper-catalyzed asymmetric reductions of aryl 2H-azirines
Palchak, Zachary L.
Unger, John B.
[J]. ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2013, 245
[10] Ligand-accelerated, copper-catalyzed asymmetric hydrosilylations of aryl ketones
Lipshutz, B.H.
Noson, K.
Chrisman, W.
[J]. 1600, American Chemical Society (123):

← 1 2 3 4 5 →