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Synthesis 2003(9): 1433-1440
DOI: 10.1055/s-2003-40196
DOI: 10.1055/s-2003-40196
SPECIALTOPIC
© Georg Thieme Verlag Stuttgart ˙ New York
Multicomponent Synthesis of Highly Substituted Imidazolines via a Silicon Mediated 1,3-Dipolar Cycloaddition
Weitere Informationen
Publikationsverlauf
Publikationsdatum:
24. Juni 2003 (online)
Abstract
A diastereoselective multicomponent synthesis of highly functionalized imidazolines is reported. A silicon mediated 1,3 dipolar cycloaddition of the in situ generated münchnone with an imine resulted in the formation of highly substituted imidazolines. The imidazolines contain a four-point diversity and two stereocenters and the cycloaddition reaction is applicable to aryl, alkyl, acyl, and heterocyclic substitutions.
Key words
imidazolines - 1,3-dipolar cycloaddition - diastereoselective - heterocycles - imidazoles
- 1
Vedejs E. Advances in Cycloaddition JAI; Greenwich CT: 1988. - 2
Padwa A.Schoffstall AM. Advances in Cycloaddition 1990, 2: 1 - 3
1,3-Dipolar Cycloaddition
Chemistry
Padwa A. Wiley; New York: 1984. Vols. 1 & 2. - 4
Harwood LM.Vickers RJ. Chem. Heterocycl. Compd. 2002, 59: 169 - 5
Synthetic Applications of
Dipolar Cycloaddition Chemistry Towards Heterocyclic and Natural
Products
Padwa A.Pearson W. Wiley-VCH; Weinheim: 2002. - 6
Terao Y.Aono M.Achiwa K. Heterocycles 1988, 27: 981 - 7
Longmire JM.Wang B.Zhang X. J. Am. Chem. Soc. 2002, 124: 13400 - 8
Gothelf AS.Gothelf KV.Hazell RG.Jorgensen KA. Angew. Chem. Int. Ed. 2002, 42: 4236 - 9
Gothelf KV.Jorgensen KA. Chem. Rev. 1998, 98: 863 - 10
Gothelf KV.Jensen KB.Jorgensen KA. Sci. Prog. 1999, 82: 327 - 11
Padwa A.Burgess EM.Gingrich HL.Roush DM. J. Org. Chem. 1982, 47: 786 - 12
Consonni R.Croce PD.Ferraccioli R.La Rosa C. J. Chem. Res., Synop. 1991, 188 - 13
Bilodeau MT.Cunningham AM. J. Org. Chem. 1998, 63: 2800 - 14
Gotthardt H.Huisgen R.Bayer HO. J. Am. Chem. Soc. 1970, 92: 4340 - 15
Croce PD.Ferraccioli R.La Rosa C. Tetrahedron 1999, 55: 201 - 16
Peddibhotla S.Jayakumar S.Tepe JJ. Org. Lett. 2002, 4: 3533 - 17
Lucet D.Le Gall T.Mioskowski C. Angew. Chem. Int. Ed. 1998, 37: 2580 - 18
Perry MC.Burges K. Tetrahedron: Asymmetry 2003, 14: 951 - 19
Hillier AC.Grasa GA.Viciu MS.Lee HM.Yang C.Nolan SP. J. Organomet. Chem. 2002, 653: 69 - 20
Alexakis A.Winn CL.Guillen F.Pytkowicz J.Roland S.Mangeney P. Adv. Synth. Catal. 2003, 345: 345 - 21
Guillen F.Winn CL.Alexakis A. Tetrahedron: Asymmetry 2001, 12: 2083 - 22
Gilbert IH.Rees DC. Tetrahedron 1995, 51: 6315 - 23
Hsiao Y.Hegedus LS. J. Org. Chem. 1997, 62: 3586 - 24
Puntener K.Hellman MD.Kuester E.Hegedus LS. J. Org. Chem. 2000, 65: 8301 - 25
Boland NA.Casey M.Hynes SJ.Matthews JW.Smyth MP. J. Org. Chem. 2002, 67: 3919 - 26
Derstine CW.Smith DN.Katzenellenbogen JA. J. Am. Chem. Soc. 1996, 118: 8485 - 27
Dghaym RD.Dhawan R.Arndtsen BA. Angew. Chem., Int. Ed. Engl. 2001, 40: 3228 - 28
Dhawan R.Dghaym RD.Arndtsen BA. J. Am. Chem. Soc. 2003, 125: 1474 - 29
Mukerjee AK. Heterocycles 1987, 26: 1077 - 30
Avalos M.Babiano R.Cintas P.Hursthouse MB.Jimenez JL.Light ME.Lopez I.Palacios JC.Silvero G. Chemistry 2001, 7: 3033 - 31
Prasad KK.Petrzilka T. Helv. Chim. Acta 1975, 58: 2504 - 32
Chen FMF.Kuroda K.Benoiton NL. Synthesis 1979, 230 - 33
Viso A.Fernandez De La Pradilla R.Guerrero-Strachan C.Alonso M.Martinez-Ripoll M.Andre II. J. Org. Chem. 1997, 62: 2316 - 34
Okada H.Akaki T.Oderaotoshi Y.Minakata S.Komatsu M. Tetrahedron 2003, 59: 197 - 35
Komatsu M.Okada H.Yokoi S.Minakata S. Tetrahedron Lett. 2003, 44: 1603 - 36
Komatsu M.Okada H.Akaki T.Oderaotoshi Y.Minakata S. Org. Lett. 2002, 4: 3505