Multicomponent Synthesis of Highly Substituted Imidazolines via a Silicon Mediated 1,3-Dipolar Cycloaddition

S. Peddibhotla; J. J. Tepe

doi:10.1055/s-2003-40196

SPECIALTOPIC

Multicomponent Synthesis of Highly Substituted Imidazolines via a Silicon Mediated 1,3-Dipolar Cycloaddition

S. Peddibhotla, J. J. Tepe*
Department of Chemistry, Michigan State University, East Lansing, MI 48824, USA
Fax: +1(517)3531793; e-Mail: tepe@cem.msu.edu;

Abstract

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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

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References

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