Manganese-Catalyzed Enantioselective Hydrogenation of Simple Ketones Using an Imidazole-Based Chiral PNN Tridentate Ligand

Fei Ling; Jiachen Chen; Sanfei Nian; Huacui Hou; Xiao Yi; Feifei Wu; Min Xu; Weihui Zhong

doi:10.1055/s-0039-1690783

Synlett, Inhaltsverzeichnis

Synlett 2020; 31(03): 285-289
DOI: 10.1055/s-0039-1690783

letter

Manganese-Catalyzed Enantioselective Hydrogenation of Simple Ketones Using an Imidazole-Based Chiral PNN Tridentate Ligand

Authors

Fei Ling

^aKey Laboratory for Green Pharmaceutical Technologies and Related Equipment of Ministry of Education, College of Pharmaceutical Sciences Zhejiang University of Technology, Hangzhou 310014, P. R. of China
Jiachen Chen

^aKey Laboratory for Green Pharmaceutical Technologies and Related Equipment of Ministry of Education, College of Pharmaceutical Sciences Zhejiang University of Technology, Hangzhou 310014, P. R. of China
Sanfei Nian

^aKey Laboratory for Green Pharmaceutical Technologies and Related Equipment of Ministry of Education, College of Pharmaceutical Sciences Zhejiang University of Technology, Hangzhou 310014, P. R. of China
Huacui Hou

^aKey Laboratory for Green Pharmaceutical Technologies and Related Equipment of Ministry of Education, College of Pharmaceutical Sciences Zhejiang University of Technology, Hangzhou 310014, P. R. of China
Xiao Yi

^aKey Laboratory for Green Pharmaceutical Technologies and Related Equipment of Ministry of Education, College of Pharmaceutical Sciences Zhejiang University of Technology, Hangzhou 310014, P. R. of China
Feifei Wu

^aKey Laboratory for Green Pharmaceutical Technologies and Related Equipment of Ministry of Education, College of Pharmaceutical Sciences Zhejiang University of Technology, Hangzhou 310014, P. R. of China
Min Xu

^bCollaborative Innovation Center of Yangtze River Delta Region Green Pharmaceuticals, Zhejiang University of Technology, Hangzhou 310014, P. R. of China eMail: weihuizhong@zju.edu.cn
Weihui Zhong∗

^aKey Laboratory for Green Pharmaceutical Technologies and Related Equipment of Ministry of Education, College of Pharmaceutical Sciences Zhejiang University of Technology, Hangzhou 310014, P. R. of China

^bCollaborative Innovation Center of Yangtze River Delta Region Green Pharmaceuticals, Zhejiang University of Technology, Hangzhou 310014, P. R. of China eMail: weihuizhong@zju.edu.cn

Abstract

Alle Artikel dieser Rubrik

Abstract

A series of Mn(I) catalysts containing imidazole-based chiral PNN tridentate ligands with controllable ‘side arm’ groups have been established, enabling the inexpensive base-promoted asymmetric hydrogenation of simple ketones with outstanding activities (up to 8200 TON) and good enantioselectivities (up to 88.5% ee). This protocol features wide substrate scope and functional group tolerance, thereby providing easy access to a key intermediate of crizotinib.

Key words

manganese - asymmetric hydrogenation - simple ketones - imidazole - tridentate ligand

Volltext

Referenzen

References

For selected examples, see:

1a Rogawski MA, Löscher W. Nat. Rev. Neurosci. 2004; 5: 553
1b Creighton CJ, Ramabadran K, Ciccone PE, Liu J, Orsini MJ, Reitz AB. Bioorg. Med. Chem. Lett. 2004; 14: 4083
1c Almeida L, Soares-Da-Silva P. Neurotherapeutics 2007; 4: 88
1d Cui JJ, Tran-Dubé M, Shen H, Nambu M, Kung P.-P, Pairish M, Jia L, Meng J, Funk L, Botrous I, McTigue M, Grodsky N, Ryan K, Padrique E, Alton G, Timofeevski S, Yamazaki S, Li Q, Zou H, Christensen J, Mroczkowski B, Bender S, Kania RS, Edwards MP. J. Med. Chem. 2011; 54: 6342

2a Noyori R, Ohkuma T. Angew. Chem. Int. Ed. 2001; 40: 40
2b Tang W, Zhang X. Chem. Rev. 2003; 103: 3029
2c Mortreux A, Karim A. The Handbook of Homogeneous Hydrogenation. Wiley-VCH; Weinheim: 2007
2d Xie J. -H, Zhou Q. -L. Acc. Chem. Res. 2008; 41: 581
2e Yang GQ, Zhang W.-B. Chem. Soc. Rev. 2018; 47: 1783
2f Zhang ZF, Butt NA, Zhang WB. Chem. Rev. 2016; 116: 14769
2g Wang ZH, Zhang ZF, Liu YG, Zhang WB. Chin. J. Org. Chem. 2016; 36: 447
2h Yuan QJ, Zhang WB. Chin. J. Org. Chem. 2016; 36: 274
2i Wang YJ, Zhang ZF, Zhang WB. Chin. J. Org. Chem. 2015; 35: 528

3 For a review, see: Zhang Z, Butt NA, Zhou M, Liu D, Zhang W. Chin. J. Chem. 2018; 36: 443

4a Shimizu H, Igarashi D, Kuriyama W, Yusa Y, Sayo N, Saito T. Org. Lett. 2007; 9: 1655
4b Junge K, Wendt B, Addis D, Zhou S, Das S, Fleischer S, Beller M. Chem. Eur. J. 2011; 17: 101
4c Krabbe SW, Hatcher MA, Bowman RK, Mitchell MB, McClure MS, Johnson JS. Org. Lett. 2013; 15: 4560
4d Zatolochnaya OV, Rodríguez S, Zhang Y, Lao KS, Tcyrulnikov S, Li G, Wang X. -J, Qu B, Biswas S, Mangunuru HP. R, Rivalti D, Sieber JD, Desrosiers J.-N, Leung JC, Grinberg N, Lee H, Haddad N, Yee NK, Song JJ, Kozlowski MC, Senanayakea CH. Chem. Sci. 2018; 9: 4505

5a Hamada Y, Koseki Y, Fujii T, Maeda T, Hibino T, Makino K. Chem. Commun. 2008; 6206
5b Hibino T, Makino K, Sugiyama T, Hamada Y. ChemCatChem 2009; 1: 237

6a Berkessel A, Reichau S, von der Höh A, Leconte N, Neudörfl J.-M. Organometallics 2011; 30: 3880
6b Gajewski P, Renom-Carrasco M, Facchini SV, Pignataro L, Lefort L, de Vries JG, Ferraccioli R, Forni A, Piarulli U, Gennari C. Eur. J. Org. Chem. 2015; 1887
6c Hodgkinson R, Del Grosso A, Clarkson GJ, Wills M. Dalton Trans. 2016; 3992

7a Zhang D, Zhu E.-Z, Lin Z.-W, Li Y.-Y, Gao J.-X. Asian J. Org. Chem. 2016; 5: 1323
7b Friedfeld MR, Shelvin M, Hoyt JM, Krska SW, Tudge MT, Chirik PJ. Science 2013; 342: 1076
7c Friedfeld MR, Margulieux GW, Schaefer B, Chirik PJ. J. Am. Chem. Soc. 2014; 136: 13178
7d Chirik PJ. Acc. Chem. Res. 2015; 48: 1687
7e Friedfeld MR, Zhong H, Ruck RT, Shelvin M, Chirik PJ. Science 2018; 360: 888
7f Monfette S, Turner ZR, Semproni SP, Chirik PJ. J. Am. Chem. Soc. 2012; 134: 4561
7g Friedfeld MR, Shevlin M, Margulieux GW, Campeau LC, Chirik PJ. J. Am. Chem. Soc. 2016; 138: 3314
7h Chen J, Chen C, Ji C, Lu Z. Org. Lett. 2016; 18: 1594

8a Wang Y, Zhu L, Shao Z, Li G, Lan Y, Liu Q. J. Am. Chem. Soc. 2019; 141: 17337
8b Kallmeier F, Kempe R. Angew. Chem. Int. Ed. 2018; 57: 46
8c Filonenko GA, van Putten R, Hensen EJ. M, Pidko EA. Chem. Soc. Rev. 2018; 47: 1459
8d Garbe M, Junge K, Beller M. Eur. J. Org. Chem. 2017; 4344
8e Maji B, Barman MK. Synthesis 2017; 49: 3377

9 Widegren MB, Harkness GJ, Slawin AM. Z, Cordes DB, Clarke ML. Angew. Chem. Int. Ed. 2017; 56: 5825
10 Garbe M, Junge K, Walker S, Wei Z, Jiao H, Spannenberg A, Bachmann S, Scalone M, Beller M. Angew. Chem. Int. Ed. 2017; 56: 11237
11 Zhang L, Tang Y, Han Z, Ding K. Angew. Chem. Int. Ed. 2019; 58: 4973

For examples of asymmetric transfer hydrogenation, see:

12a Zirakzadeh A, de Aguiar SR. M. M, Stöger B, Widhalm M, Kirchner K. ChemCatChem 2017; 9: 1744
12b Wang D, Bruneau-Voisine A, Sortais J.-B. Catal. Commun. 2018; 105: 31
12c Demmans KZ, Olson ME, Morris RH. Organometallics 2018; 37: 4608

13 Ling F, Nian S, Chen J, Luo W, Wang Z, Lv Y, Zhong W. J. Org. Chem. 2018; 83: 10749

14a Ling F, Hou H, Chen J, Nian S, Yi X, Wang Z, Song D, Zhong W. Org. Lett. 2019; 11: 3937
14b Luo W, Hu H, Nian S, Qi L, Ling F, Zhong W. Org. Biomol. Chem. 2017; 15: 7523
14c Zhu L, Hu H, Qi L, Zheng Y, Zhong W. Eur. J. Org. Chem. 2016; 2139
14d Hu H, Yu S, Zhu L, Zhou L, Zhong W. Org. Biomol. Chem. 2016; 14: 752
14e Tu A, Hu H, Du T, Zhong W. Synth. Commun. 2014; 44: 3392
14f Tang Q, Tu A, Deng Z, Hu M, Zhong W. Chin. J. Org. Chem. 2013; 33: 954

15 General Procedure for the Preparation of Ligands: A solution of (S _C , R _FC )-1 (1 mmol), benzimidazole aldehyde (1.1 mmol) in anhydrous MeOH was stirred at 60 °C for 10–12 h, The reaction was cooled to room temperature, then NaBH₄ (3 mmol) was added and the mixture was heated to 60 °C again, and stirred at this temperature for 4 h. The solvent was removed under vacuum, and the crude ligand was purified by column chromatography on silica gel. L2: Orange solid (432.0 mg, 75% yield); mp 84–85 °C; [α]_D ²⁰ = +120.0 (c = 0.5, CHCl₃). ¹H NMR (600 MHz, CDCl₃): δ = 7.71 (d, J = 7.8 Hz, 1 H), 7.55–7.53 (m, 2 H), 7.2–7.36 (m, 3 H), 7.21–7.14 (m, 8 H), 7.09–7.07 (m, 3 H), 7.02–6.99 (m, 1 H), 6.85–6.83 (m, 2 H), 5.03 (d, J = 16.8 Hz, 1 H), 4.87 (d, J = 16.8 Hz, 1 H), 4.48 (s, 1 H), 4.31 (s, 1 H), 4.17–4.15 (m, 1 H), 3.95 (s, 5 H), 3.86 (s, 1 H), 3.74 (d, J = 13.8 Hz, 1 H), 3.65 (d, J = 13.8 Hz, 1 H), 1.52 (d, J = 6.6 Hz, 3 H). ¹³C NMR (150 MHz, CDCl₃): δ = 153.1, 142.4, 140.5 (d, J = 10.5 Hz), 137.6 (d, J = 9.0 Hz), 136.6, 135.7, 135.3, 135.1, 132.5, 132.4, 129.2, 128.7, 128.2, 128.12, 128.07, 127.8, 127.5, 126.3, 122.4, 121.8, 119.5, 109.6, 97.8 (d, J = 25.5 Hz), 75.0 (d, J = 9.0 Hz), 71.3 (d, J = 4.5 Hz), 69.7, 69.3, 69.0 (d, J = 4.5 Hz), 51.4 (d, J = 9.0 Hz), 46.4, 44.0, 20.0. ³¹P NMR (162 MHz, CDCl₃): δ = –24.25. HRMS (ESI): m/z [M + H]⁺ calcd for C₃₉H₃₆FeN₃P: 634.2069; found: 634.1996.
16 Liao S, Sun X.-L, Tang Y. Acc. Chem. Res. 2014; 47: 2260
17 de Koning PD, McAndrew D, Moore R, Moses IB, Boyles DC, Kissick K, Stanchina CL, Cuthbertson T, Kamatani A, Rahman L, Rodriguez R, Urbina A, Sandoval A, Rose PR. Org. Process Res. Dev. 2011; 15: 1018
18 General Procedure for the Asymmetric Hydrogenation of Ketones Under an argon atmosphere, a vial was charged with Mn(CO)₅Br/L2 (0.1 mol%) and KOH (2 mol%), which were dissolved in dried MeOH (2 mL). The resulting red solution was stirred briefly before the ketone (1 mmol) was added. The vial was placed in an alloy plate that was then placed into an autoclave. The autoclave was purged five times with hydrogen, then pressurized to 3.0 Mpa, and stirred at room temperature for 10 h. After slowly releasing the hydrogen pressure, the solvent was removed, and the mixture was purified by passing through a short column of silica gel to afford the corresponding alcohol. The ee values of all compounds were determined by HPLC analysis with a chiral column. (R)-1-(4-Methoxyphenyl)ethan-1-ol (4k): Colorless oil (150.4 mg, 99% yield); 84.9% ee (R); [α]_D ²⁰ = +41.5 (c = 0.5, CHCl₃). HPLC conditions: Chiralpak OJ-H column, hexane/isopropanol = 95:5; flow rate = 0.8 mL/min; UV detection at 220 nm; (S) = 33.74 min (minor), (R) = 35.98 min (major). ¹H NMR (600 MHz, CDCl₃): δ = 7.25 (d, J = 8.4 Hz, 2 H), 6.84 (d, J = 9.0 Hz, 2 H), 4.78 (q, J = 6.0 Hz, 1 H), 3.76 (s, 3 H), 2.57 (brs, 1 H), 1.43 (d, J = 6.6 Hz, 3 H). ¹³C NMR (150 MHz, CDCl₃): δ = 158.9, 138.1, 126.7, 113.8, 69.8, 55.3, 25.0. (R)-1-(2,6-Dichloro-3-fluorophenyl)ethan-1-ol (4m): Colorless oil (182.2 mg, 88% yield); 85.1% ee (R); [α]_D ²⁰ = –13.1 (c = 0.5, CHCl₃). HPLC conditions: Chiralpak OD-H column, hexane/isopropanol = 90:10 flow rate = 0.8 mL/min; UV detection at 220 nm; (S) = 13.31 min (minor), (R) = 14.02 min (major). ¹H NMR (400 MHz, CDCl₃): δ = 7.32–7.28 (dd, J = 8.8, 4.8 Hz,1 H), 7.06 (dd, J = 16.8, 8.4 Hz, 1 H), 5.64 (q, J = 7.2 Hz, 1 H), 2.84 (brs, 1 H), 1.69 (d, J = 6.8 Hz, 3 H). ¹³C NMR (100 MHz, CDCl₃): δ = 157.3; (¹ J _C–F = 248 Hz), 140.5, 129.6; (³ J _C–F = 7 Hz), 128.3, 121.5, 115.6; (² J _C–F = 23 Hz), 68.4, 21.0.

Zusatzmaterial

Supporting Information (PDF)