Login Register Cart 0
Generic placeholder image

Current Organocatalysis

Editor-in-Chief

ISSN (Print): 2213-3372
ISSN (Online): 2213-3380

Back
Journal Home About Journal Editorial Board Journal Insight Current Issue Volumes/Issues
Subscribe
Research Article

Ionic Liquid Supported Organocatalysts for the Asymmetric Mannich- Type Reaction of α-cyano α-sulfonyl Carbanions

Author(s): Vivek Srivastava*

Volume 10, Issue 4, 2023

Published on: 20 July, 2023

Page: [297 - 303] Pages: 7

DOI: 10.2174/2213337210666230516145640

Price: $65

Abstract

Introduction: We synthesized proline functionalized ionic liquid and further characterized it with analytical techniques.

Method: After getting proper structural information on the above ionic liquid, we utilized them as a catalyst for the asymmetric Mannich-Type Reaction.

Result: We synthesized 6 different types of β-amino α-cyano sulfones derivatives as Mannich adduct using various combinations of different imines and aryl sulphonyl as pre-nucleophiles.

Conclusion: We obtained the corresponding chiral Mannich adduct followed by simple ether washing in excellent yield and stereoselectivity. We recycled the catalyst up to 6 runs without losing the catalytic activity.

« Previous Next »
Graphical Abstract

[1]
Oliveira VdaG, Cardoso MFDC. Organocatalysis: A brief overview on its evolution and applications. Catalysts 2018; 8: 605.
[2]
Upadhyay P, Srivastava V. Proline based organocatalysis: Supported and unsupported approach. Curr Organocatal 2016; 3(3): 243-69.
[http://dx.doi.org/10.2174/2213337202666150812230640]
[3]
Shaikh IR. Organocatalysis: Key trends in green synthetic chemistry, challenges, scope towards heterogenization, and importance from research and industrial point of view. J Catal 2014; 2014: 1-35.
[http://dx.doi.org/10.1155/2014/402860]
[4]
Govender T, Arvidsson PI, Maguire GEM, Kruger HG, Naicker T. Enantioselective organocatalyzed transformations of β-ketoesters. Chem Rev 2016; 116(16): 9375-437.
[http://dx.doi.org/10.1021/acs.chemrev.6b00156] [PMID: 27463615]
[5]
MacMillan DWC. The advent and development of organocatalysis. Nature 2008; 455(7211): 304-8.
[http://dx.doi.org/10.1038/nature07367] [PMID: 18800128]
[6]
Vekariya RL. A review of ionic liquids: Applications towards catalytic organic transformations. J Mol Liq 2017; 227: 44-60.
[http://dx.doi.org/10.1016/j.molliq.2016.11.123]
[7]
Lei Z, Chen B, Koo YM, MacFarlane DR. Introduction: Ionic liquids. Chem Rev 2017; 117(10): 6633-5.
[http://dx.doi.org/10.1021/acs.chemrev.7b00246] [PMID: 28535681]
[8]
Pal R, Mukhopadhyay C. Organocatalysis: An overview of its application in oxidation and reduction reactions. Curr Organocatal 2021; 9: 4-13.
[9]
De Carvalho GSG, Granato ÁS, De Castro PP, Amarante GW. Recent contributions of nuclear magnetic resonance in organocatalysis mechanism elucidation. Curr Organocatal 2019; 7(1): 7-22.
[http://dx.doi.org/10.2174/2213337206666190328210907]
[10]
Srivastava V. Preparation of ionic liquid supported organocatalysts for the synthesis of stereoselective (R)-9-Methyl-5(10)-Octaline-1,6-Dione. Curr Organocatal 2022; 10(1): 26-33.
[11]
Nitabaru T, Kumagai N, Shibasaki M. Catalytic asymmetric nitro-Mannich reactions with a Yb/K heterobimetallic catalyst. Molecules 2010; 15(3): 1280-90.
[http://dx.doi.org/10.3390/molecules15031280] [PMID: 20335980]
[12]
Banik BK. Advances in organocatalysis. Curr Organocatal 2019; 5(3): 164-4.
[http://dx.doi.org/10.2174/221333720503190214105527]
[13]
Srivastava V. Ionic liquid mediated recyclable sulphonimide based organocatalysis for aldol reaction. Cent Eur J Chem 2010; 8: 269-72.
[14]
Kelemen Z, Hollóczki O, Nagy J, Nyulászi L. An organocatalytic ionic liquid. Org Biomol Chem 2011; 9(15): 5362-4.
[http://dx.doi.org/10.1039/c1ob05639e] [PMID: 21701727]
[15]
Ni B, Headley AD. Ionic-liquid-supported (ILS) catalysts for asymmetric organic synthesis. Chemistry 2010; 16(15): 4426-36.
[http://dx.doi.org/10.1002/chem.200902747] [PMID: 20235242]
[16]
Kotrusz P, Kmentova I, Gotov B, Toma S, Solcaniova E. Proline-catalyzed asymmetric aldol reaction in the room temperature ionic liquid [bmim]PF6. ChemInform 2003; 34(11): 34.
[http://dx.doi.org/10.1002/chin.200311083]
[17]
Miao W, Chan TH. Ionic-liquid-supported organocatalyst: Efficient and recyclable ionic-liquid-anchored proline for asymmetric aldol reaction. Adv Synth Catal 2006; 348(12-13): 1711-8.
[http://dx.doi.org/10.1002/adsc.200606059]
[18]
Chen Z, Li Y, Xie H, Hu C, Dong X. Ionic liquid-supported proline as catalyst in direct asymmetric aldol reaction. Russ J Org Chem 2008; 44(12): 1807-10.
[http://dx.doi.org/10.1134/S1070428008120154]
[19]
Patil PG, Satkar Y, More DH. L-proline based ionic liquid: A highly efficient and homogenous catalyst for synthesis of 5-benzylidene-1,3-Dimethylpyrimidine-2,4,6(1H,3H,5H)-Trione and pyrano[2,3-d] pyrimidine diones under ultrasonic irradiation. Synth Commun 2020; 50(24): 3804-19.
[http://dx.doi.org/10.1080/00397911.2020.1811987]
[20]
Kong Y, Tan R, Zhao L, Yin D. l-Proline supported on ionic liquid-modified magnetic nanoparticles as a highly efficient and reusable organocatalyst for direct asymmetric aldol reaction in water. Green Chem 2013; 15(9): 2422-33.
[http://dx.doi.org/10.1039/c3gc40772a]
[21]
Suzuki Y. Asymmetric michael addition and related reactions mediated by chiral ionic liquids. Mini Rev Org Chem 2017; 15(3): 236-45.
[22]
Banik BK. Current organocatalysis and synthetic methods. Curr Organocatal 2019; 6(2): 78-8.
[http://dx.doi.org/10.2174/221333720602190513074850]
[23]
Rita VM. Asymmetric syntheses based on organocatalysis. Mini Rev Org Chem 2014; 11(2): 154-63.
[http://dx.doi.org/10.2174/1570193X1102140609120227]
[24]
Headley AD. Ionic Liquid-Supported Organocatalysts for Asymmetric Organic Synthesis. Sustainable Catalysis in Ionic Liquids 2018; pp. 31-55.
[http://dx.doi.org/10.1201/9781315148694-2]
[25]
Zhuo C, Xian D, Jian-wei W, Hui X. An efficient and recyclable ionic liquid-supported proline catalyzed knoevenagel condensation. ISRN Org Chem 2011; 2011: 1-5.
[http://dx.doi.org/10.5402/2011/676789] [PMID: 24052829]
[26]
Terrier F, Kizilian E, Goumont R, Faucher N, Wakselman C. α-Sulfonyl carbanions: Combined kinetic, thermodynamic, and NMR approaches for the study of the ionization of benzyltriflones in Me2SO and H2O-Me2SO mixtures. J Am Chem Soc 1998; 120(37): 9496-503.
[http://dx.doi.org/10.1021/ja9806074]
[27]
Boche G. The structure of lithium compounds of sulfones, sulfoximides, sulfoxides, thioethers and 1,3-dithianes, nitriles, nitro compounds and hydrazones. Angew Chem Int Ed Engl 1989; 28(3): 277-97.
[http://dx.doi.org/10.1002/anie.198902771]
[28]
Cid MB, López-Cantarero J, Duce S, Ruano JLG. Enantioselective organocatalytic approach to the synthesis of α,α-disubstituted cyanosulfones. J Org Chem 2009; 74(1): 431-4.
[http://dx.doi.org/10.1021/jo801968p] [PMID: 19053610]
[29]
Ohmatsu K, Goto A, Ooi T. Catalytic asymmetric mannich-type reactions of α-cyano α-sulfonyl carbanions. Chem Commun 2012; 48(64): 7913-5.
[http://dx.doi.org/10.1039/c2cc32398b] [PMID: 22662327]
[30]
Faraji L, Arvinnezhad H, Alikami N, Jadidi K. Synthesis of pyrrolizidine derivatives in ionic liquid [bmim]. Br Lett Org Chem 2010; 7(6): 472-4.
[http://dx.doi.org/10.2174/157017810791824946]
[31]
Yulin H, Yao N, Wu PY, Zheng BK. Recent advances in catalytic condensation reactions applications of supported ionic liquids. Curr Org Chem 2017; 22(1): 462-84.
[32]
Zalewska K, Branco CL. Organocatalysis with Chiral Ionic Liquids. Mini Rev Org Chem 2014; 11: 141-53.
[http://dx.doi.org/10.2174/1570193X1102140609120011]
[33]
Kaur P, Chopra HK. Recent advances in applications of supported ionic liquids. Curr Org Chem 2020; 23(26): 2881-915.
[http://dx.doi.org/10.2174/1385272823666191204151803]
[34]
Xin B, Jia C, Li X. Supported ionic liquids: Efficient and reusable green media in organic catalytic chemistry. Curr Org Chem 2015; 20(5): 616-28.
[http://dx.doi.org/10.2174/1385272819666150825220817]
[35]
Nielsen M, Jacobsen CB, Holub N, Paixão MW, Jørgensen KA. Asymmetric organocatalysis with sulfones. Angew Chem Int Ed 2010; 49(15): 2668-79.
[http://dx.doi.org/10.1002/anie.200906340] [PMID: 20209543]
[36]
Blakemore PR. The modified julia olefination: Alkene synthesis via the condensation of metallated heteroarylalkylsulfones with carbonyl compounds. J Chem Soc Perkin 1 2002; 2: 2563-85.
[37]
Nemcsok T, Rapi Z, Bagi P, et al. Enantioselective cyclopropanation of conjugated cyanosulfones using carbohydrate-based crown ether catalysts. Tetrahedron 2020; 76(9): 130965.
[http://dx.doi.org/10.1016/j.tet.2020.130965]
[38]
Lee JH, Kim DY. Enantio- and diastereoselective mannich-type reactions of α-cyano ketones with N -boc aldimines catalyzed by chiral bifunctional urea. Adv Synth Catal 2009; 351(11-12): 1779-82.
[http://dx.doi.org/10.1002/adsc.200900268]
[39]
Aitken LS, Hammond LE, Sundaram R, Shankland K, Brown GD, Cobb AJA. Asymmetric cyclopropanation of conjugated cyanosulfones using a novel cupreine organocatalyst: Rapid access to δ 3 -amino acids. Chem Commun 2015; 51(70): 13558-61.
[http://dx.doi.org/10.1039/C5CC05158D] [PMID: 26223465]

Rights & Permissions Print Cite
© 2024 Bentham Science Publishers | Privacy Policy