Recent Progress in Hydrogen Bond-Mediated Transformations to Chiral Medicinal Drugs by Phosphoric Acid and Thiourea Derived Organocatalysts

Tian, J.; Zhong, J.; Li, Y.; Ma, D. Organocatalytic and scalable synthesis of the anti-influenza drugs zanamivir, laninamivir, and CS-8958. Angew. Chem. Int. Ed. Engl., 2014, 53(50), 13885-13888.
[http://dx.doi.org/10.1002/anie.201408138] [PMID: 25314609]

(a)Yuan, H-N.; Wang, S.; Nie, J.; Meng, W.; Yao, Q.; Ma, J-A. Hydrogen-bond-directed enantioselective decarboxylative Mannich reaction of β-ketoacids with ketimines: application to the synthesis of anti-HIV drug DPC 083. Angew. Chem. Int. Ed. Engl., 2013, 52(14), 3869-3873.
[http://dx.doi.org/10.1002/anie.201210361] [PMID: 23460261]
(b)Yuan, H-N.; Li, S.; Nie, J.; Zheng, Y.; Ma, J-A. Highly enantioselective decarboxylative Mannich reaction of malonic acid half oxyesters with cyclic trifluoromethyl ketimines: synthesis of β-amino esters and anti-HIV drug DPC 083. Chemistry, 2013, 19(47), 15856-15860.
[http://dx.doi.org/10.1002/chem.201303307] [PMID: 24150893]
(c)Jiang, X.; Wang, Y.; Zhang, G.; Fu, D.; Zhang, F.; Kai, M.; Wang, R. Enantioselective synthesis of cyclic thioureas via Mannich reaction and concise synthesis of highly optically active methylthioimidazolines: discovery of a more potent antipyretic agent. Adv. Synth. Catal., 2011, 353, 1787-1796.
[http://dx.doi.org/10.1002/adsc.201100288]
(d)Jiang, X.; Sun, Y.; Yao, J.; Cao, Y.; Kai, M.; He, N.; Zhang, X.; Wang, Y.; Wang, R. Core scaffold-inspired concise synthesis of chiral spirooxindole-pyranopyrimidines with broad-spectrum anticancer potency. Adv. Synth. Catal., 2012, 354, 917-925.
[http://dx.doi.org/10.1002/adsc.201100792]
(e)Zhang, G.; Zhang, Y.; Yan, J.; Chen, R.; Wang, S.; Ma, Y.; Wang, R. One-pot enantioselective synthesis of functionalized pyranocoumarins and 2-amino-4H-chromenes: discovery of a type of potent antibacterial agent. J. Org. Chem., 2012, 77(2), 878-888.
[http://dx.doi.org/10.1021/jo202020m] [PMID: 22148387]

(a)Yu, H.; Dai, G.; He, Q-R.; Tang, J-J. Enantioselective synthesis and evaluation of 4-styryldihydropyrimidin-2-thiones as anti-proliferative agents. Med. Chem. Res., 2017, 26, 787-795.,
[http://dx.doi.org/10.1007/s00044-017-1790-4]
(b)Hammer, N.; Erickson, J.D.; Lauridsen, V.H.; Jakobsen, J.B.; Hansen, B.K.; Jacobsen, K.M.; Poulsen, T.B.; Jørgensen, K.A. Catalytic asymmetric [4+2]-cycloadditions using tropolones: developments, scope, transformations, and bioactivity. Angew. Chem. Int. Ed. Engl., 2018, 57(40), 13216-13220.
[http://dx.doi.org/10.1002/anie.201808221] [PMID: 30133090]
(c)Li, M.; Zhao, X.; Yang, W.; Zhong, F.; Yuan, L.; Ren, Q. Asymmetric synthesis and biological evaluation of 3-nitro-2H-chromenes as potential antibacterial agents. Tetrahedron Lett., 2018, 59, 3511-3515.
[http://dx.doi.org/10.1016/j.tetlet.2018.07.046]

Bhadury, P.S.; Sun, Z. Axially chiral Brønsted acid catalyzed transformations of electrophilic imines. Curr. Org. Chem., 2014, 18, 127-150.
[http://dx.doi.org/10.2174/138527281801140121154544]

(a)Ghosh, A.K.; Cheng, X.; Bai, R.; Hamel, E. Total synthesis of potent antitumor macrolide, (-)-zampanolide: An oxidative intramolecular cyclization-based strategy. Eur. J. Org. Chem., 2012, 2012(22), 4130-4139.
[http://dx.doi.org/10.1002/ejoc.201200286] [PMID: 23606808]
(b)Wang, Z.; Ai, F.; Wang, Z.; Zhao, W.; Zhu, G.; Lin, Z.; Sun, J. Organocatalytic asymmetric synthesis of 1,1-diarylethanes by transfer hydrogenation. J. Am. Chem. Soc., 2015, 137(1), 383-389.
[http://dx.doi.org/10.1021/ja510980d] [PMID: 25482291]
(c)Zhou, L-J.; Zhang, Y-C.; Jiang, F.; He, G.; Yan, J.; Lu, H.; Zhang, S.; Shi, F. Enantioselective construction of cyclic enaminone-based 3-substituted 3-amino-2-oxindole scaffolds via catalytic asymmetric additions of isatin-derived imines. Adv. Synth. Catal., 2016, 358, 3069-3083.
[http://dx.doi.org/10.1002/adsc.201600508]

(a)Min, C.; Lin, Y.; Seidel, D. Catalytic enantioselective synthesis of Mariline A and related Isoindolinones through a biomimetic approach. Angew. Chem. Int. Ed. Engl., 2017, 56(48), 15353-15357.
[http://dx.doi.org/10.1002/anie.201709182] [PMID: 29024305]
(b)Wang, Y-B.; Zheng, S-C.; Hu, Y-M.; Tan, B. Brønsted acid-catalysed enantioselective construction of axially chiral arylquinazolinones. Nat. Commun., 2017, 8(1), 15489.
[http://dx.doi.org/10.1038/ncomms15489] [PMID: 28524863]

(a)Yang, X.; Toste, F.D. Direct asymmetric amination of α-branched cyclic ketones catalyzed by a chiral phosphoric acid. J. Am. Chem. Soc., 2015, 137(9), 3205-3208.
[http://dx.doi.org/10.1021/jacs.5b00229] [PMID: 25719604]
(b)Kim, Y.; Lee, J.; Jung, J.; Kim, S-G. Chiral Brønsted acid-catalyzed Friedel–Crafts reaction of 3-indolylsulfamidates with indoles: Synthesis of enantioenriched bisindolylmethane sulfamates. Tetrahedron Lett., 2019, 60, 1625-1630.
[http://dx.doi.org/10.1016/j.tetlet.2019.05.003]
(c)Cheng, X.; Vellalath, S.; Goddard, R.; List, B. Direct catalytic asymmetric synthesis of cyclic aminals from aldehydes. J. Am. Chem. Soc., 2008, 130(47), 15786-15787.
[http://dx.doi.org/10.1021/ja8071034] [PMID: 18975905]
(d)Wakchaure, V.N.; Zhou, J.; Hoffmann, S.; List, B. Catalytic asymmetric reductive amination of α-branched ketones. Angew. Chem. Int. Ed. Engl., 2010, 49(27), 4612-4614.
[http://dx.doi.org/10.1002/anie.201001715] [PMID: 20491115]
(e)Liu, H.; Dagousset, G.; Masson, G.; Retailleau, P.; Zhu, J. Chiral Brønsted acid-catalyzed enantioselective three-component Povarov reaction. J. Am. Chem. Soc., 2009, 131(13), 4598-4599.
[http://dx.doi.org/10.1021/ja900806q] [PMID: 19334771]
(f)Goss, J.M.; Schaus, S.E. Enantioselective synthesis of SNAP-7941: chiral dihydropyrimidone inhibitor of MCH1-R. J. Org. Chem., 2008, 73(19), 7651-7656.
[http://dx.doi.org/10.1021/jo801463j] [PMID: 18767801]

Li, X.; Duan, M.; Deng, Z.; Shao, Q.; Chen, M.; Zhu, G.; Houk, K.N.; Sun, J. Catalytic enantioselective synthesis of chiral tetraarylmethanes.Nat. Catal., 2020, 3, 1010-1019.,
[http://dx.doi.org/10.1038/s41929-020-00535-4]

Han, B.; He, X-H.; Liu, Y-Q.; He, G.; Peng, C.; Li, J-L. Asymmetric organocatalysis: an enabling technology for medicinal chemistry. Chem. Soc. Rev., 2021, 50(3), 1522-1586.
[http://dx.doi.org/10.1039/D0CS00196A] [PMID: 33496291]

Bhadury, P.S.; Li, H. Organocatalytic asymmetric hydrophosphonylation/Mannich reactions using thiourea, cinchona and Brønsted acid catalysts. Synlett, 2012, 23(8), 1108-1131.
[http://dx.doi.org/10.1055/s-0031-1290193]