RSS-Feed abonnieren
Bitte kopieren Sie die angezeigte URL und fügen sie dann in Ihren RSS-Reader ein.
https://www.thieme-connect.de/rss/thieme/de/10.1055-s-00000084.xml
Synthesis 2009(22): 3744-3750
DOI: 10.1055/s-0029-1217013
DOI: 10.1055/s-0029-1217013
PAPER
© Georg Thieme Verlag
Stuttgart ˙ New YorkMerrifield Resin Supported Ionic Liquids/l-Proline as Efficient and Recyclable Catalyst Systems for Asymmetric Aldol Reaction
Weitere Informationen
Received
3 June 2009
Publikationsdatum:
23. September 2009 (online)
Publikationsverlauf
Publikationsdatum:
23. September 2009 (online)

Abstract
Merrifield resin supported ionic liquids/l-proline as efficient and recyclable catalyst systems for asymmetric aldol reaction have been developed. l-Proline with Merrifield resin supported ionic liquids can catalyze asymmetric aldol reaction smoothly and generate the corresponding products in good to excellent yields and ee values. In addition, the supported catalyst systems can be recycled simply by filtration and reused for five times without significant decrease in activity.
Key words
Merrifield resin - organocatalyst - aldol reaction - l-proline - ionic liquids - supported catalysts
- 1a
Heathcock CH. In Comprehensive Organic Synthesis Vol. 2:Trost BM.Fleming I.Heathcock CH. Pergamon; Oxford: 1991. Chap. 1.5.Reference Ris Wihthout Link - 1b
Heathcock CH. In Comprehensive Organic Synthesis Vol. 2:Trost BM.Fleming I.Heathcock CH. Pergamon; Oxford: 1991. Chap. 1.6.Reference Ris Wihthout Link - 1c
Kim BM.Williams SF.Masamune S. In Comprehensive Organic Synthesis Vol. 2:Trost BM.Fleming I.Heathcock CH. Pergamon; Oxford: 1991. Chap. 1.7.Reference Ris Wihthout Link - 2a
Mukaiyama T. Tetrahedron 1999, 55: 8609Reference Ris Wihthout Link - 2b
Nicolaou KC.Vourloumis D.Wissinger N.Baran PS. Angew. Chem. Int. Ed. 2000, 39: 44Reference Ris Wihthout Link - 2c
Evans DA.Ratz AM.Huff BE.Sheppard GS. J. Am. Chem. Soc. 1995, 117: 3448Reference Ris Wihthout Link - 2d
Narasaka K.Pai FC. Tetrahedron 1984, 40: 2233Reference Ris Wihthout Link - 2e
Keck GE.Wager CA.Sell T.Wager TT. J. Org. Chem. 1999, 64: 2172Reference Ris Wihthout Link - For examples, see:
- 3a
Barbas CF.Heine A.Zhong G.Hoffmann T.Gramatikova S.Björnestedt R.List B.Anderson J.Stura EA.Wilson IA.Lerner RA. Science 1997, 278: 2085Reference Ris Wihthout Link - 3b
Hoffmann T.Zhong G.List B.Shabat D.Anderson J.Gramatikova S.Lerner RA.Barbas CF. J. Am. Chem. Soc. 1998, 120: 2768Reference Ris Wihthout Link - 3c
List B.Shabat D.Barbas CF.Lerner RA. Chem. Eur. J. 1998, 4: 881Reference Ris Wihthout Link - 4a
Yamada YMA.Yoshikawa N.Sasai H.Shibasaki M. Angew. Chem., Int. Ed. 1997, 36: 1871Reference Ris Wihthout Link - 4b
Yoshikawa N.Yamada YMA.Das J.Sasai H.Shibasaki M. J. Am. Chem. Soc. 1999, 121: 4168Reference Ris Wihthout Link - 5a
Hartikka A.Arvidsson PI. Tetrahedron: Asymmetry 2004, 15: 1831Reference Ris Wihthout Link - 5b
Torii H.Nakadai M.Ishihara K.Saito S.Yamamoto H. Angew. Chem. Int. Ed. 2004, 43: 1983Reference Ris Wihthout Link - 5c For a review, see:
Saito S.Yamamoto H. Acc. Chem. Res. 2004, 37: 570Reference Ris Wihthout Link - For recent reviews, see:
- 6a
Silvestri MG.Desantis G.Mitchell M.Wong C.-H. Top. Stereochem. 2003, 23: 267Reference Ris Wihthout Link - 6b
Sukumaran J.Hanefeld U. Chem. Soc. Rev. 2005, 34: 530Reference Ris Wihthout Link - 6c
Samland AK.Sprenger GA. Appl. Microbiol. Biotechnol. 2006, 71: 253Reference Ris Wihthout Link - 7a
Reymond J.-L. J. Mol. Catal. B: Enzym. 1998, 5: 331Reference Ris Wihthout Link - 7b
Zhu X.Tanaka F.Hu Y.Heine A.Fuller R.Zhong G.Olson AJ.Lerner RA.Barbas CF.Wilson IA. J. Mol. Biol. 2004, 343: 1269Reference Ris Wihthout Link - 8
Movassaghi M.Jacobsen EN. Science 2002, 298: 1904 - 9a
Eder U.Sauer G.Wiechert R. Angew. Chem., Int. Ed. Engl. 1971, 10: 496Reference Ris Wihthout Link - 9b
Hajos ZG.Parrish DR. J. Org. Chem. 1974, 39: 1615Reference Ris Wihthout Link - 10a
List B.Lerner RA.Barbas CF. J. Am. Chem. Soc. 2000, 122: 2395Reference Ris Wihthout Link - 10b
Sakthivel K.Notz W.Bui T.Barbas CF. J. Am. Chem. Soc. 2001, 123: 5260Reference Ris Wihthout Link - 11
Cordova A.Zou W.Dziedzic P.Ibrahem I.Reyes E.Xu Y. Chem. Eur. J. 2006, 12: 5383 - 12
List B. Chem. Commun. 2006, 819 - 13
Miao W.Chan T.-H. Adv. Synth. Catal. 2006, 348: 1711 - 14
Gruttadauria M.Giacalone F. Eur. J. Org. Chem. 2007, 4688 - 15
Yan J.Wang L. Synthesis 2008, 2065 - 16
Fernandez-Lopez R.Kofoed J.Machuqueiro M.Darbre T. Eur. J. Org. Chem. 2005, 5268 - 17
Chandrasekhar S.Reddy NR.Sultana SS.Narsihmulu C.Reddy KV. Tetrahedron 2006, 62: 338 - 18
Zhou Y.Shan Z. Tetrahedron: Asymmetry 2006, 17: 1671 - 19
Zhou L.Wang L. Chem. Lett. 2007, 36: 628 - 20
Choudary BM.Chakrapani L.Ramani T.Kumar KV.Kantam ML. Tetrahedron 2006, 62: 9571 - 21
Chen J.-R.An X.-L.Zhu X.-Y.Wang X.-F.Xiao W.-J. J. Org. Chem. 2008, 74: 6006 - 22
Lei M.Shi L.-X.Li G.Chen S.-L.Fang W.-H.Ge Z.-M.Cheng T.-M.Li R.-T. Tetrahedron 2007, 63: 7892 - 23
Gu Q.Wang X.-F.Wang L.Wu X.-Y.Zhou Q.-L. Tetrahedron: Asymmetry 2006, 17: 1537