Synthesis of spiro[bicyclo[2.2.1]heptane-2,2′-furan]-3-amines via stereoselective cycloadditions of trimethylenemethane to (1S,3EZ,4R)-3-arylimino-1,7,7-trimethylbicyclo[2.2.1]heptan-2-ones

Tetrahedron Asymmetry

Volumn 18, Issue 19, 2007, Pages 2365-2376

  Grošelj, Uroš ^a   Meden, Anton ^a   Stanovnik, Branko ^a   Svete, Jurij ^a  

^a UNIVERSITY OF LJUBLJANA   (Slovenia)

Author keywords

[No Author keywords available]

Indexed keywords

3 ARYLIMINO 1,7,7 TRIMETHYLBICYCLO[2.2.1]HEPTAN 2 ONE; AMINE; AMINOALCOHOL; CARBON; DIAMINE; EXOCYCLIC DOUBLE BOND; FURAN DERIVATIVE; HEPTANE DERIVATIVE; METHANE; NITROGEN; PYRROLIDINE DERIVATIVE; SPIRO[BICYCLO[2.2.1]HEPTANE 2,2' FURAN] 3 AMINE; TRIMETHYLENEMETHANE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL BOND; CHIRALITY; CYCLOADDITION; NUCLEAR MAGNETIC RESONANCE; NUCLEAR OVERHAUSER EFFECT; PRIORITY JOURNAL; REDUCTION; STEREOCHEMISTRY; STEREOSPECIFICITY; STRUCTURE ANALYSIS; X RAY DIFFRACTION;

EID: 35348833604     PISSN: 09574166     EISSN: 1362511X     Source Type: Journal    
DOI: 10.1016/j.tetasy.2007.09.018     Document Type: Article

References (50)

1. Money T. Nat. Prod. Rep. (1985) 253-289
2. Oppolzer W. Tetrahedron 43 (1987) 1969-2004
3. Oppolzer W. Pure Appl. Chem. 62 (1990) 1241-1250
4. Money T. Remote Functionalization of Camphor: Application to Natural Product Synthesis. Organic Synthesis: Theory and Applications Vol. 3 (1996), JAI Press 1-83
5. Kitamura M., Suga S., Kawai K., and Noyori R. J. Am. Chem. Soc. 108 (1986) 6071-6072
6. Nugent W. Chem. Commun. (1999) 1369-1370
7. García C., and Walsh P.J. Org. Lett. 5 (2003) 3641-3644
8. Bunlaksananusorn T., Polborn K., and Knochel P. Angew. Chem., Int. Ed. 42 (2003) 3941-3943
9. Bunlaksananusorn T., and Knochel P. J. Org. Chem. 69 (2004) 4595-4601
10. Kadyrov R., Ilaldinov I.Z., Almena J., Monsees A., and Riermeier T.H. Tetrahedron Lett. 46 (2005) 7397-7400
11. Stanovnik B., and Svete J. Targets Heterocycl. Syst. 4 (2000) 105-137
12. Stanovnik B., and Svete J. Synlett (2000) 1077-1091
13. Svete J. J. Heterocycl. Chem. 39 (2002) 437-454
14. Stanovnik B., and Svete J. Chem. Rev. 104 (2004) 2433-2480 and references cited therein
15. Svete J. Monatsh. Chem. 135 (2004) 629-647
16. Stanovnik B., and Svete J. Mini-Rev. Org. Chem. 2 (2005) 211-224
17. Pirc S., Bevk D., Jakše R., Rečnik S., Golič L., Golobič A., Meden A., Stanovnik B., and Svete J. Synthesis (2005) 2969-2988
18. Pirc S., Bevk D., Golobič A., Stanovnik B., and Svete J. Helv. Chim. Acta 89 (2006) 30-44
19. Jakše R., Bevk D., Golobič A., Svete J., and Stanovnik B. Z. Naturforsch. 61b (2006) 1-7
20. Časar Z., Bevk D., Svete J., and Stanovnik B. Tetrahedron 61 (2005) 7508-7519
21. Wagger J., Bevk D., Meden A., Svete J., and Stanovnik B. Helv. Chim. Acta 89 (2006) 240-248
22. Wagger J., Golič Grdadolnik S., Grošelj U., Meden A., Stanovnik B., and Svete J. Tetrahedron: Asymmetry 18 (2007) 464-475
23. Grošelj U., Rečnik S., Svete J., Meden A., and Stanovnik B. Tetrahedron: Asymmetry 13 (2002) 821-833
24. Grošelj U., Bevk D., Jakše R., Meden A., Stanovnik B., and Svete J. Tetrahedron: Asymmetry 17 (2006) 79-91
25. Grošelj U., Bevk D., Jakše R., Meden A., Stanovnik B., and Svete J. Tetrahedron: Asymmetry 16 (2005) 2927-2945
26. Grošelj U., Bevk D., Jakše R., Rečnik S., Meden A., Stanovnik B., and Svete J. Tetrahedron 61 (2005) 3991-3998
27. Grošelj U., Bevk D., Jakše R., Meden A., Pirc S., Rečnik S., Stanovnik B., and Svete J. Tetrahedron: Asymmetry 15 (2004) 2367-2383
28. Grošelj U., Bevk D., Jakše R., Meden A., Rečnik S., Stanovnik B., and Svete J. Synthesis (2005) 1087-1094
29. Grošelj U., Bevk D., Jakše R., Pirc S., Stanovnik B., Svete J., and Meden A. Tetrahedron: Asymmetry 16 (2005) 2187-2197
30. Grošelj U., Bevk D., Jakše R., Meden A., Stanovnik B., and Svete J. Tetrahedron: Asymmetry 17 (2006) 1217-1237
31. Grošelj U., Rečnik S., Meden A., Stanovnik B., and Svete J. Acta Chim. Slov. 53 (2006) 245-256
32. Grošelj U., Tavčar G., Bevk D., Meden A., Žemva B., Stanovnik B., and Svete J. Tetrahedron: Asymmetry 17 (2006) 1715-1727
33. Denmark S.E., and Rivera I. J. Org. Chem. 59 (1994) 6887-6889
34. Trost B.M., and Marrs C.M. J. Am. Chem. Soc. 115 (1993) 6636-6645
35. Chan D.M.T. In: Kobayashi S., and Jørgensen K.A. (Eds). Recent Advances in Palladium-Catalyzed Cycloadditions Involving Trimethylenemethane and its Analogs. Cycloaddition Reactions in Organic Synthesis (2001), Wiley-VCH, Weinheim, Germany 57-84
36. McClure N.L., Dai G.-Y., and Mosher H.S. J. Org. Chem. 53 (1988) 2617-2620
37. Richer J.-C., and Rossi A. Can. J. Chem. 50 (1972) 1376-1385
38. Van Toan V., and Lightner D.A. Tetrahedron 43 (1987) 5769-5774
39. Nevalainen M., and Nevalainen V. Tetrahedron: Asymmetry 12 (2001) 1771-1777
40. Oppolzer W., and Chapius C. Tetrahedron Lett. 25 (1984) 5383-5386
41. Abraham R.J., and Fisher J. Magn. Reson. Chem. 23 (1985) 862-871
42. Abraham R.J., and Fisher J. Magn. Reson. Chem. 24 (1986) 451-459
43. Karplus M. J. Chem. Phys. 30 (1959) 11-15
44. Singh B.K., Basu-Mallik H., and Bhaduri B. J. Indian Chem. Soc. 8 (1931) 95-117
45. Collect Software. Nonius, BV, Delft, The Netherlands, 1998.
46. Otwinowski Z., and Minor W. Methods Enzymol. 276 (1997) 307-326
47. Altomare A., Burla M.C., Camalli M., Cascarano G.L., Giacovazzo C., Guagliardi A., Moliterni A.G.G., Polidori G., and Spagna R. J. Appl. Crystallogr. 32 (1999) 115-119
48. Hall S.R., King G.S.D., and Stewart J.M. The Xtal3.4 User's Manual (1995), University of Western Australia, Lamb, Perth
49. Burnett, M. N.; Johnson, C. K. In ortep-III: Oak Ridge Thermal Ellipsoid Plot Program for Crystal Structure Illustrations, Oak Ridge National Laboratory Report ORNL-6895, 1996.
50. Wang H., and Robertson B.E. In: Wilson A.J.C. (Ed). Structure and Statistics in Crystallography (1985), Adenine Press, New York