Ruthenium-Catalyzed Asymmetric Reduction of Isoxazolium Salts: Access to Optically Active Δ4-IsoxazolinesClick to copy article linkArticle link copied!
Abstract
A tethered MsDPEN–ruthenium catalyst reduces a series of isoxazolium salts, affording optically active Δ4-isoxazolines in moderate to good yields and enantioenrichment. The redundancy of heating or high pressures allowed for chemoselective reduction with no subsequent heterocyclic ring opening. Our results reinforce our understanding of the workings of these Noyori-class catalysts.
Cited By
Smart citations by scite.ai include citation statements extracted from the full text of the citing article. The number of the statements may be higher than the number of citations provided by ACS Publications if one paper cites another multiple times or lower if scite has not yet processed some of the citing articles.
This article is cited by 16 publications.
- Dongxu He, Chen Xu, Xiangyou Xing. Developing Ru-Catalysts for Asymmetric Transfer Hydrogenation of Acyclic Imines. Organic Letters 2022, 24
(45)
, 8354-8358. https://doi.org/10.1021/acs.orglett.2c03385
- Asuka Matsunami, Marika Ikeda, Hitomi Nakamura, Minori Yoshida, Shigeki Kuwata, Yoshihito Kayaki. Accessible Bifunctional Oxy-Tethered Ruthenium(II) Catalysts for Asymmetric Transfer Hydrogenation. Organic Letters 2018, 20
(17)
, 5213-5218. https://doi.org/10.1021/acs.orglett.8b02157
- Xiaohan Li, Ji Yang, Zhenni He, Wei Huang, Jianbo Yang, Huanrong Li, Lijin Xu, Qian Shi. Asymmetric Transfer Hydrogenation of 3‐Substituted 2
H
‐1,4‐Benzoxazines under Tethered Cp*Rh(III)‐Diamine Catalysis with Unexpected Reversal of Enantioselectivity. Advanced Synthesis & Catalysis 2025, 367
(5)
https://doi.org/10.1002/adsc.202401307
- Zhenni He, Ji Yang, Xiaohan Li, Wei Huang, Kai Liu, Lijin Xu, Qian Shi. Iridium‐Catalyzed Asymmetric Transfer Hydrogenation for Facile Access to Optically Active Dihydrodibenzo‐Fused Azepines. Advanced Synthesis & Catalysis 2025, 367
(5)
https://doi.org/10.1002/adsc.202401200
- Garazi Talavera, Alejandro Santana Fariña, Antonio Zanotti-Gerosa, Hans Günter Nedden. Strukturelle Vielfalt in Ruthenium-katalysierten asymmetrischen Transferhydrierungsreaktionen. 2024, 77-122. https://doi.org/10.1007/978-3-031-52858-3_3
- Tian-Ming Liao, Wen-Jiang Ma, Yu-Ning Gao, Ming Bian, Min Jiang, Jin-Tao Liu, Hui-Yu Chen, Zhen-Jiang Liu. Facile synthesis of (polyfluoro)alkanesulfinyl 4-isoxazolines: a stepwise solvent- and catalyst-free approach or a one-pot process in water. Green Chemistry 2023, 25
(13)
, 5233-5239. https://doi.org/10.1039/D3GC00557G
- Yingkun Yan, Min Li, Min Liu, Min Huang, Lianyi Cao, Wenzhe Li, Xiaomei Zhang. Sc(OTf)
3
‐Catalyzed Dearomative [3+2] Annulation of 5‐Aminoisoxazoles with Quinone Imine Ketals or Quinone Monoacetals. European Journal of Organic Chemistry 2022, 2022
(18)
https://doi.org/10.1002/ejoc.202200067
- Franca M. Cordero, Donatella Giomi, Fabrizio Machetti. Isoxazoles. 2022, 308-434. https://doi.org/10.1016/B978-0-12-818655-8.00135-9
- K. K. Banerji. Oxidation and Reduction. 2021, 69-136. https://doi.org/10.1002/9781119531975.ch3
- You‐Song Cheng, Shih‐Hsien Chan, Gunda Ananda Rao, Ramani Gurubrahamam, Kwunmin Chen. Enantioselective Aza‐Friedel‐Crafts Reaction of Heteroarenes with
in situ
Generated Isoxazolium Ions via Chiral Phosphoric Acid Catalysis. Advanced Synthesis & Catalysis 2021, 363
(14)
, 3502-3506. https://doi.org/10.1002/adsc.202100408
- Ashish A. Mishra, Bhalchandra M. Bhanage. Ru‐TsDPEN catalysts and derivatives in asymmetric transfer hydrogenation reactions. Chirality 2021, 33
(7)
, 337-378. https://doi.org/10.1002/chir.23317
- Vijyesh K. Vyas, Richard C. Knighton, Martin Wills. Tethered Ruthenium(
II
) Catalysts in Asymmetric Transfer Hydrogenation. 2021, 221-254. https://doi.org/10.1002/9783527822294.ch7
- Chang Wang, Fan Chen, Pengcheng Qian, Jiang Cheng. Recent advances in the Rh-catalyzed cascade arene C–H bond activation/annulation toward diverse heterocyclic compounds. Organic & Biomolecular Chemistry 2021, 19
(8)
, 1705-1721. https://doi.org/10.1039/D0OB02377A
- Shichao Yang, Hongji Li, Pinhua Li, Jingya Yang, Lei Wang. Room temperature iron(
ii
)-catalyzed radical cyclization of unsaturated oximes with hypervalent iodine reagents. Organic & Biomolecular Chemistry 2020, 18
(4)
, 715-724. https://doi.org/10.1039/C9OB02424G
- Garazi Talavera, Alejandro Santana Fariña, Antonio Zanotti-Gerosa, Hans Günter Nedden. Structural Diversity in Ruthenium-Catalyzed Asymmetric Transfer Hydrogenation Reactions. 2019, 73-114. https://doi.org/10.1007/3418_2019_27
- Renta Jonathan Chew, Martin Wills. Exploitation of differential electronic densities for the stereoselective reduction of ketones bearing a masked amino surrogate. Journal of Catalysis 2018, 361 , 40-44. https://doi.org/10.1016/j.jcat.2018.02.014
Article Views are the COUNTER-compliant sum of full text article downloads since November 2008 (both PDF and HTML) across all institutions and individuals. These metrics are regularly updated to reflect usage leading up to the last few days.
Citations are the number of other articles citing this article, calculated by Crossref and updated daily. Find more information about Crossref citation counts.
The Altmetric Attention Score is a quantitative measure of the attention that a research article has received online. Clicking on the donut icon will load a page at altmetric.com with additional details about the score and the social media presence for the given article. Find more information on the Altmetric Attention Score and how the score is calculated.