Efficient Kinetic Resolution in the Asymmetric Transfer Hydrogenation of 3-aryl-indanones: Applications to a Short Synthesis of (+)-indatraline and a Formal Synthesis of ()-tolterodine

Overview

Journal RSC Adv

Publisher Royal Society of Chemistry

Specialty Chemistry

Date 2022 Apr 28

PMID 35480442

Authors

Songsoon Park

Hyeon-Kyu Lee

Affiliations

Soon will be listed here.

Abstract

Efficient kinetic resolution (KR) occurs in asymmetric transfer hydrogenation (ATH) reactions of racemic 3-aryl-1-indanones using commercial (,)- or (,)-Ts-DENEB as a catalyst, a 1 : 5 mixture of HCOH and EtN as a hydrogen source and MeOH as solvent. This process at room temperature produces near equal yields of -3-arylindanols with high dr and ee, and unreacted 3-arylindanones with excellent ee. Stereoselective transformations of 3-arylindanols and 3-arylindanones, generated by using the ATH-KR protocol, were carried out to form (+)-indatraline and synthetically valuable ()-6-methyl-4-phenylcoumarine, which is a key intermediate in the preparation of ()-tolterodine, ()-4-aryl-3,4-dihydroquinoline-2(1)-one and ()-4-aryl-3,4-dihydroisoquinoline-1(2)-one.

Citing Articles

Characterization and Metabolism of Drug Products Containing the Cocaine-Like New Psychoactive Substances Indatraline and Troparil.

Manier S, Mumber P, Zapp J, Eckstein N, Meyer M Metabolites. 2024; 14(6).

PMID: 38921476 PMC: 11205633. DOI: 10.3390/metabo14060342.

References

Bianco G, Ferraz H, Costa A, Costa-Lotufo L, Pessoa C, de Moraes M . (+)- and (-)-mutisianthol: first total synthesis, absolute configuration, and antitumor activity. J Org Chem. 2009; 74(6):2561-6. DOI: 10.1021/jo9000405. View

Qin X, Yao Lee M, Zhou J . Asymmetric Hydroarylation of Enones via Nickel-Catalyzed 5- Cyclization. Org Lett. 2019; 21(15):5990-5994. DOI: 10.1021/acs.orglett.9b02130. View

Nedden H, Zanotti-Gerosa A, Wills M . The Development of Phosphine-Free "Tethered" Ruthenium(II) Catalysts for the Asymmetric Reduction of Ketones and Imines. Chem Rec. 2016; 16(6):2619-2639. DOI: 10.1002/tcr.201600084. View

Chen G, Tokunaga N, Hayashi T . Rhodium-catalyzed asymmetric 1,4-addition of arylboronic acids to coumarins: asymmetric synthesis of (R)-tolterodine. Org Lett. 2005; 7(11):2285-8. DOI: 10.1021/ol0507367. View

Bogeso K, Arnt J, Boeck V, Christensen A, Hyttel J, Jensen K . Antihypertensive activity in a series of 1-piperazino-3-phenylindans with potent 5-HT2-antagonistic activity. J Med Chem. 1988; 31(12):2247-56. DOI: 10.1021/jm00120a003. View

Minatti A, Zheng X, Buchwald S . Synthesis of chiral 3-substituted indanones via an enantioselective reductive-Heck reaction. J Org Chem. 2007; 72(24):9253-8. DOI: 10.1021/jo701741y. View

Borie C, Ackermann L, Nechab M . Enantioselective syntheses of indanes: from organocatalysis to C-H functionalization. Chem Soc Rev. 2016; 45(5):1368-86. DOI: 10.1039/c5cs00622h. View

Dub P, Ikariya T . Quantum chemical calculations with the inclusion of nonspecific and specific solvation: asymmetric transfer hydrogenation with bifunctional ruthenium catalysts. J Am Chem Soc. 2013; 135(7):2604-19. DOI: 10.1021/ja3097674. View

Clark W, Kassick A, Plotkin M, Eldridge A, Lantos I . A highly enantioselective conjugate reduction of 3-arylinden-1-ones using bakers' yeast for the preparation of (S)-3-arylindan-1-ones. Org Lett. 2000; 1(11):1839-42. DOI: 10.1021/ol991111+. View

10.

Patil S, Patil R, Patil S . Recent developments in biological activities of indanones. Eur J Med Chem. 2017; 138:182-198. DOI: 10.1016/j.ejmech.2017.06.032. View

11.

Yoo K, Kim H, Yun J . Asymmetric synthesis of 1,1-diarylalkyl units by a copper hydride catalyzed reduction: differentiation between two similar aryl substituents. Chemistry. 2009; 15(42):11134-8. DOI: 10.1002/chem.200901262. View

12.

Rendy R, Zhang Y, McElrea A, Gomez A, Klumpp D . Superacid-catalyzed reactions of cinnamic acids and the role of superelectrophiles. J Org Chem. 2004; 69(7):2340-7. DOI: 10.1021/jo030327t. View

13.

Yu H, Kim I, Folk J, Tian X, Rothman R, Baumann M . Synthesis and pharmacological evaluation of 3-(3,4-dichlorophenyl)-1-indanamine derivatives as nonselective ligands for biogenic amine transporters. J Med Chem. 2004; 47(10):2624-34. DOI: 10.1021/jm0305873. View

14.

Wei W, Yeh J, Kuo T, Wu H . Highly enantioselective rhodium-catalyzed asymmetric 1,4-addition reactions of arylboronic acids to acyclic α,β-unsaturated compounds: the formal synthesis of (-)-indatraline. Chemistry. 2011; 17(41):11405-9. DOI: 10.1002/chem.201102073. View

15.

Gallagher B, Taft B, Lipshutz B . Asymmetric conjugate reductions of coumarins. A new route to tolterodine and related coumarin derivatives. Org Lett. 2009; 11(23):5374-7. DOI: 10.1021/ol9020404. View

16.

Touge T, Nara H, Kida M, Matsumura K, Kayaki Y . Convincing Catalytic Performance of Oxo-Tethered Ruthenium Complexes for Asymmetric Transfer Hydrogenation of Cyclic α-Halogenated Ketones through Dynamic Kinetic Resolution. Org Lett. 2021; 23(8):3070-3075. DOI: 10.1021/acs.orglett.1c00739. View

17.

Atsumi T, Murakami Y, Shibuya K, Tonosaki K, Fujisawa S . Induction of cytotoxicity and apoptosis and inhibition of cyclooxygenase-2 gene expression, by curcumin and its analog, alpha-diisoeugenol. Anticancer Res. 2005; 25(6B):4029-36. View

18.

Yu Y, Xu M . Enantioselective synthesis of chiral 3-aryl-1-indanones through rhodium-catalyzed asymmetric intramolecular 1,4-addition. J Org Chem. 2013; 78(6):2736-41. DOI: 10.1021/jo302656s. View

19.

Ikariya T, Blacker A . Asymmetric transfer hydrogenation of ketones with bifunctional transition metal-based molecular catalysts. Acc Chem Res. 2007; 40(12):1300-8. DOI: 10.1021/ar700134q. View

20.

Rast S, Modec B, Stephan M, Mohar B . γ-Sultam-cored N,N-ligands in the ruthenium(ii)-catalyzed asymmetric transfer hydrogenation of aryl ketones. Org Biomol Chem. 2016; 14(6):2112-20. DOI: 10.1039/c5ob02352a. View