Synthesis of New Functionalized Chiral Ionic Liquid and Its Organocatalytic Asymmetric Michael Addition

REFERENCES

• (a) Baudequin , C. ; Baudoux , J. ; Levillain , J. ; Cahard , D. ; Gaumontb , A. C. ; Plaqueventa , J. C. Ionic liquids and chirality: Opportunities and challenges . Tetrahedron: Asymmetry 2003 , 14 , 3081 – 3093 ; (b) Parvulescu , V. I. ; Hardacre , C. Catalysis in ionic liquids . Chem. Rev. 2002 , 107 ( 6 ), 2615 – 2665 ; (c) Hallett , J. P. ; Welton , T. W. Room-temperature ionic liquids: Solvents for synthesis and catalysis, 2 . Chem. Rev. 2011 , 111 ( 5 ), 3508 – 3576 .
   Google Scholar
• (a) Miao , W. S. ; Chan , T. H. Ionic-liquid-supported synthesis: A novel liquid-phase strategy for organic synthesis. Acc. Chem. Res. 2006, 39, 897–908; (b) Howarth , J. ; Hanlon , K. ; Fayne , D. ; McCormac , P. Moisture-stable dialkylimidazolium salts as heterogeneous and homogeneous Lewis acids in the Diels–Alder reaction. Tetrahedron Lett. 1997, 38, 3097–3100; (c) Earle , M. J. ; McCormac , P. B. ; Seddon , K. R. Diels–Alder reactions in ionic liquids. Green Chem. 1999, 1, 23–25; (d) Ni , B. ; Headley , A. D. Ionic-liquid-supported (ILS) catalysts for asymmetric organic synthesis. Chem. Eur. J. 2010, 16, 4426–4436; (e) Luo , S. ; Zhang , L. ; Cheng , J. P. Functionalized chiral ionic liquids: A new type of asymmetric organocatalysts and nonclassical chiral ligands. Asian J. 2009, 4, 1184–1195.
   PubMed Web of Science ®Google Scholar
• (a) Pégot , B. ; Vo-Thanh , G. ; Gori , D. ; Loupy , A. First application of chiral ionic liquids in asymmetric Baylis–Hillman reaction . Tetrahedron Lett. 2004 , 45 , 6425 – 6428 ; (b) Gausepohl , R. ; Buskens , P. ; Kleinen , J. ; Bruckmann , A. ; Lehmann , C. W. ; Klankermayer , J. ; Leitner , W. Highly enantioselective aza-Baylis–Hillman reaction in a chiral reaction medium . Angew. Chem. Int. Ed. 2006 , 45 , 3689 – 3692 .
   Web of Science ®Google Scholar
• (a) Wu , L. Y. ; Yan , Z. Y. ; Xie , Y. X. ; Niu , Y. N. ; Liang , Y. M. Ionic-liquid-supported organocatalyst for the enantioselective Michael addition of ketones to nitroolefins . Tetrahedron: Asymmetry 2007 , 18 , 2086 – 2090 ; (b) Xu , D. Q. ; Wang , B. T. ; Luo , S. P. ; Yue , H. D. ; Wang , L. P. ; Xu , Z. Y. Pyrrolidine–pyridinium-based organocatalysts for highly enantioselective Michael addition of cyclohexanone to nitroalkenes . Tetrahedron: Asymmetry 2007 , 18 , 1788 – 1794 ; (c) Maltsev , O. V. ; Kucherenko , A. S. ; Beletskaya , I. P. ; Tartakovsky , V. A. ; Zlotin , S. G. Chiral ionic liquids bearing O-silylated α,α -diphenyl(S)- or (R)-prolinol units: Recoverable organocatalysts for asymmetric Michael addition of nitroalkanesto α,β-enals . Eur. J. Org. Chem. 2010 , 2927 – 2933 .
   Web of Science ®Google Scholar
• (a) Miao , W. S. ; Chan , T. H. Ionic-liquid-supported organocatalyst: Efficient and recyclable ionic-liquid-anchored proline for asymmetric aldol reaction . Adv. Synth. Catal. 2006 , 348 , 1711 – 1718 ; (b) Siyutkin , D. E. ; Kucherenko , A. S. ; Struchkova , M. I. ; Zlotin , S. G. A novel (S)-proline-modified task-specific chiral ionic liquid—An amphiphilic recoverable catalyst for direct asymmetric aldol reactions in water . Tetrahedron Lett. 2008 , 49 , 1212 – 1216 .
   Web of Science ®Google Scholar
• (a) Ishii , T. ; Fujioka , S. ; Sekiguchi , Y. ; Kotsuki , H. A new class of chiral pyrrolidine-pyridine conjugate base catalysts for use in asymmetric Michael additionreactions . J. Am. Chem. Soc. 2004 , 126 , 9558 – 9559 (b) Wang , W. ; Wang , J. ; Li , H. Highly enantioselective pyrrolidine sulfonamide–catalyzed Michael addition of aldehydes to nitrostyrenes . Angew. Chem. Int. Ed. 2005 , 44 , 1369 – 1371 ; (c) Hayashi , Y. ; Gotoh , H. ; Hayashi , T. ; Shoji , M. Diphenylprolinol silyl ethers as efficient organocatalysts for the asymmetric Michael reaction of aldehydes and nitroalkenes . Angew. Chem. Int. Ed. 2005 , 44 , 4212 – 4215 ; (d) Pansare , S. V. ; Pandya , K. Simple diamine- and triamine-protonic acid catalysts for the enantioselective Michael addition of cyclic ketones to nitroalkenes . J. Am. Chem. Soc. 2006 , 128 , 9624 – 9625 ; (e) Cao , C.-L. ; Ye , M.-C. ; Sun , X.-L. ; Tang , Y. Pyrrolidine–thiourea as a bifunctional organocatalyst: Highly enantioselective Michael addition of cyclohexanone to nitroolefins . Org. Lett. 2006 , 8 , 2901 – 2904 ; (f) Singh , V. K.V. Highly enantioselective water-compatible organocatalyst for Michael reaction of ketones to nitroolefins . Org. Lett. 2007 , 9 , 1117 – 1119 .
   PubMed Web of Science ®Google Scholar
• (a) List , B. ; Pojarliev , P. ; Martin , H. J. Efficient proline-catalyzed Michael additions of unmodified ketones to nitro olefins . Org. Lett. 2001 , 3 , 2423 – 2425 ; (b) Enders , D. ; Seki , A. Proline-catalyzed enantioselective Michael additions of ketones to nitrostyrene . Synlett. 2002 , 1 , 26 – 28 ; (c) Betancort , J. M. ; Barbas III , C. F. Catalytic direct asymmetric Michael reactions: Taming naked aldehyde donor . Org. Lett. 2001 , 3 , 3737 – 3740 .
   PubMed Web of Science ®Google Scholar
• (a) Zhang , B. N. ; Headley , A. D. Asymmetric Michael addition reactions of aldehydes with nitrostyrenes catalyzed by functionalized chiral ionic liquids. Tetrahedron 2008, 64, 5091–5097; (b) Luo , S. ; Mi , X. ; Liu , S. ; Xu , P. L. ; Cheng , J.-P. Surfactant-type asymmetric organocatalyst: Organocatalytic asymmetric Michael addition to nitrostyrenes in water. Chem. Commun. 2006, 3687–3689; (c) Ni , B. ; Zhang , Q. ; Dhungana , K. ; Headley , A. D. Ionic liquid–supported (ILS) (S)-pyrrolidine sulfonamide, a recyclable organocatalyst for the highly enantioselective Michael addition to nitroolefins. Org. Lett. 2009, 11, 1037–1040.
   Web of Science ®Google Scholar
• Dahlin , N. A. ; Boegevig , H. ; Adolfsson , H. N-Arenesulfonyl-2-amino methyl pyrrolidines: Novel modular ligands and organocatalysts for asymmetric catalysis . Adv. Synth. Catal. 2004 , 346 , 1101 – 1105 .
   Web of Science ®Google Scholar
• Kumaran , G. ; Kulkarni , G. H. Effect of the α -alkyl substituent of conjugated nitroolefins on the formation of cyclic nitronic esters vs. nitrocyclopropanes in their reaction with sulfur ylides . Synthesis 1995 , 1545 – 1548 .
   Web of Science ®Google Scholar
• Yee , Y. K. ; Bernstein , P. R. ; Adams , E. J. ; Brown , F. J. ; Cronk , L. A. ; Hebbel , K. C. ; Vacek , E. P. ; Krell , R. D. ; Snyder , D. W. A novel series of selective leukotriene antagonists: Exploration and optimization of the acidic region in 1,6-disubstituted indoles and indazoles . J. Med. Chem. 1990 , 33 , 2437 – 2451
   Web of Science ®Google Scholar
• Li , P. ; Wang , L. ; Zhang , Y. ; Wang , G. Silica-gel-supported pyrrolidine-based chiral ionic liquid as recyclable organocatalyst for asymmetric Michael addition to nitrostyrenes . Tetrahedron 2008 , 64 , 7633 – 7638 .
   Web of Science ®Google Scholar
• Cao , C. L. ; Ye , M. C. ; Sun , X. L. ; Tang , Y. Pyrrolidine-thiourea as a bifunctional organocatalyst: Highly enantioselective Michael addition of cyclohexanone to nitroolefins . Org. Lett. 2006 , 8 , 2901 – 2904 .
   PubMed Web of Science ®Google Scholar