|
You can download a recent Research Presentation on the work of the group on Asymmetric Transfer Hydrogenation.
ASYMMETRIC TRANSFER HYDROGENATION (ATH) USING TETHERED CATALYSTS - PRACTICAL and VERSATILE.
. (search for 'teth').
A video of how to run an ATH reaction is below:
Recent applications of the tethered catalyst by other groups, in industry and academia:
Excellent application of ATH where the 3C tethered catalyst is the best of a series tested for a key reduction in the synthesis of (-)-paroxetine. . Lei Liu, Xianjing Zhou, Wenfeng Huang and Sunliang Cui, Org. Lett. 2025, 27, 5532–5535.
Great application of the 3C tethered catalyst in the ATH of a challenging diketone, where it outperformed other ATH catalysts tested: . St茅phany Bouzid, Antony Marcoux, Thierry Ollevier, Chem – Eur. J. 2024, 30, e202402449. Thanks for using our catalyst!
An excellent application of ATH, where the tethered catalyst was used to reduce some of the substrate examples: , Prabhakara R. Tharra, Jir铆虒 S虒vejkar, Abhijeet S. Jadhav, Marek Necas, 虒 Pavel A. Dub, Mathew D. Halls and Jakub S虒venda, J. Org. Chem. 2024, 89, 12902鈭�12911.
Great application to ATH of alpha-amino ketones using the 3C-tethered catalyst; , Hari P. R. Mangunuru* Leila Terrab, Venumadhav Janganati, Nageswara Rao Kalikinidi, Srinivasarao Tenneti, Vasudevan Natarajan, Arun D. R. Shada, Santhosh Reddy Naini, Praveen Gajula, Daniel Lee, Lalith P. Samankumara, Manasa Mamunooru, Aravindan Jayaraman, Rajkumar Lalji Sahani, Jinya Yin, Chathuranga C. Hewa-Rahinduwage, Aravind Gangu, Anji Chen, Zhirui Wang, Bimbisar Desai, Tai Y. Yue, Chaitanya S. Wannere, Joseph D. Armstrong III, Kai O. Donsbach, Gopal Sirasani, B. Frank Gupton, Bo Qu*, and Chris H. Senanayake*, J. Org. Chem. 2024, 89, 6085-6099. Thanks for using the tethered catalyst!
, Raphael J. Zachmann, Kenzo Yahata, Mira Holzheimer, Maxime Jarret, Cornelia Wirtz, and Alois F眉rstner, J. Am. Chem. Soc. 2023, 145, 4, 2584–2595. And earlier: Heiko Sommer and Alois F眉rstner, Org. Lett. 2016, 18, 13, 3210–3213.
Great application with the 3C tethered catalyst providing the best result: , Francesco Scorzelli, Giusy Tassone, Daniele Padula and Matteo Zacch猫, Eur. J. Org. Chem. 2022, e202200490.
Use of tethered Rh and Ru catalysts in a fantastic synthesis by Merck and co: : Application toward the Synthesis of GPR40 Agonist MK-2305, Yong-Li Zhong, Yining Ji, Heather Wang, Xiao Wang, and Donald R. Gauthier, Org. Lett. 2022, 24, 17, 3254-3258.
A great application to a BF3-containing C=N asymmetric hydrogenation, with the 3C tethered catalyst the best of a set of catalysts tested: Andrej 艩terman, Izidor Sosi膷 and Zdenko 膶asar, Chem. Sci. 2022,13, 2946-2953. Thanks for using our catalyst!
, Claudio Cianferotti, Giuseppe Barreca, Venkatesh Bollabathini, Luca Carcone, Damian Grainger, Samantha Staniland and Maurizio Taddei, Eur J. Org. Chem. 2021, 1924-1930.
An excellent ATH/DKR application using the 3C catalyst:
, Zhichao Xiong, Jiangyan Tian, Peng Xue, Xumu Zhang and Hui Lv, Org. Chem. Front., 2020,7, 104-108. The tethered catalyst used for same application as DENEB in JACS 2019, 141, 16354-16361.
Application to the ATH of alpha-keto amides:
Ashish A. Mishra Prof. Bhalchandra M. Bhanage, Chemistry Select, 2019, 4, 14032-14035.
An excellent application to an ATH-DKR of a complex substrate using the 3C catalyst:
, Adam Rolt, Paul M. O鈥橬eill, T. Jake Liang and Andrew V. Stachulski, RSC Advances, 2019, 9, 40336 - 40339.
An elegant application of the 3C-tethered catayst to the reduction of a cyclic ketone, with it outperfoming other ATH catalysts:
, Cheng-Yi Chen and Xiaowei Lu, Org. Lett. 2019, 21, .
Jason Burch et al (Genentech and Pharmaron Beijing) reported an elegant synthesis of a selective interleukin-2 inducible T-cell kinase (ITK) inhibitor using the 3C tethered catalyst at a key point:
. Jared Moore, Kevin Lau, Xiaofeng Xu, Yamin Zhang and Jason D.Burch, Tetrahedron Lett. 2019, 60, 785-788.
Xumu Zhang et al. used the 3C catalyst in a fantastic dynamic kinetic resolution application:
by Zhichao Xiong, Chengfeng PEi, Peng Xue, Hui Lv and Xumu Zhang, Chem. Commun. 2018, 54, 3883-3886.
An application reported by Pfizer using the 3C catalyst:
,
Shengquan Duan* , Bryan Li, Robert W. Dugger, Brian Conway, Rajesh Kumar, Carlos Martinez, Teresa Makowski, Robert Pearson, Mark Olivier, and Roberto Colon-Cruz (Pfizer) Org. Process Res. Dev., 2017, 21, 1340–1348. Use of the tethered catalysts, alongside other ATH catalysts, in a fantastic industrial application which highlights the tremedous value of this class of catalyst in industrial applications. Although not selected for final use in the preparation of 400 kg of intermediate, it gave an excellent result in the screen (99.9% conv and 99.7% ee - the highest ee of the set.
Use of the 3C tethered catalyst in a Dynamic Kinetic Resolution Reaction:
, Vijyesh K. Vyas and Bhalchandra M. Bhanage, Organic Letters 2016, 18, 8436-6439.
Use of the 3C tethered catalyst with 1,4-butanediol as a reducing agent:
.
Russell J. Wakeham, James A. Morris and Jonathan M. J. Williams, ChemCatChem 2015, 7, 4039-4041. Use of the tethered catalyst inketone reduction, with 1,4-butenediol used as a hydrogen source.
An application of the 3C tethered catalyst in C=N reduction by Merck:
''
Ian K. Mangion , Cheng-yi Chen, Hongmei Li , Peter Maligres , Yonggang Chen , Melodie Christensen , Ryan Cohen , Ingyu Jeon , Artis Klapars , Shane Krska , Hoa Nguyen , Robert A. Reamer , Benjamin D. Sherry , and Ilia Zavialov, Org. Lett., 2014, 16, 2310–2313 - a synthesis of MK-8742 by Merck uses tethered catalyst in a C=N reduction.
An application to asymmetric lactone synthesis using the 3C catalyst:
'' Yan Su, Yong-Qiang Tu, and Peiming Gu, Org. Lett., 2014, 16 (16), pp 4204–4207A study of a combined cyclopropane opening / asymmetric reduction / cyclisation in one pot using the tethered catalyst.
An application to azido acrylate reduction usign the 3C catalyst:
by J Ji, P. Xue, D.-D. Ma, X.-Q. Li, P. Gu and R. Li Tetrahedron Lett. 2015, 56, 192-194.
The tethered catalyst has also been used by several companies in work reported in patents.
|
