Chapter 12 Ring rearrangement metathesis (RRM) - A new concept in piperidine and pyrrolidine synthesis

Strategies and Tactics in Organic Synthesis

Volumn 4, Issue C, 2004, Pages 315-346

  Basra, Sandeep ^a   Blechert, Siegfried ^a  

^a TECHNISCHE UNIVERSITÄT BERLIN   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 33749256319     PISSN: 18746004     EISSN: None     Source Type: Book Series    
DOI: 10.1016/S1874-6004(04)80016-9     Document Type: Chapter

References (81)

1. Watson P.S., Jiang B., and Scott B. Org. Lett. 2 (2000) 3679
2. Doernyei G., Incze M., Moldvai I., and Szantay C. Synthetic Commun. 33 (2003) 2329
3. Holsworth D.D., Bakir R., Uyeda R.T., Ge Y., Lau J., Hansen T.K., and Andersen H.S. Synth Commun. 33 (2003) 1789
4. Hedley S.J., Moran W.J., Price D.A., and Harrity J.P.A. J. Org. Chem. 68 (2003) 4286
5. Dhavale D.D., Matin M.M., Sharma T., and Sabharwal S.G. Bioorg. Med. Chem. 11 (2003) 3295
6. Kumar A.R., Reddy J.S., and Rao B.V. Tetrahedron Lett. 44 (2003) 5687
7. Lee J., Reynolds C., Jetter M.C., Youngman M.A., Hlasta D.J., Dax S.L., Stone D.J., Zhang S.-P., and Codd E.E. Bioorg. Med. Chem. Lett. 13 (2003) 1879
8. Bailey P.D., Millwood P.A., and Smith P.D. J.C.S. Chem. Commun. (1998) 633
9. Laschat S., and Dickner T. Synthesis (2000) 1781
10. Connon Stephen J., and Blechert S. Angew. Chem. Int. Ed. Engl. 42 (2003) 1900
11. Fürstner A. Angew. Chem. Int. Ed. Engl. 39 (2000) 3012
12. Roy R., and Das S.K. Chem. Commun. (2000) 519
13. Philips A.J., and Abell A.D. Aldrichim. Acta 32 (1999) 75
14. Armstrong S.K. J.C.S.Perkin Trans. 1 (1998) 371
15. Grubbs R.H., and Chang S. Tetrahedron 54 (1998) 4413
16. Ivin K.J. J. Mol. Catal. A 133 (1998) 1
17. Alkene Metathesis in Organic Synthesis (1998), Springer, Berlin
18. Randall M.L., and Snapper M.L. J. Mol. Catal. A 133 (1998) 29
19. Schuster M., and Blechert S. Angew. Chem. Int. Ed. Engl. 36 (1997) 2037
20. Nguyen S.T., Grubbs R.H., and Ziller J.W. J. Am. Chem. soc. 115 (1993) 9858
21. Schwab P., France M.B., Ziller J.W., and Grubbs R.H. Angew. Chem. Int. Ed. Engl. 34 (1995) 2039
22. Schwab P., Grubbs R.H., and Ziller J.W. J. Am. Chem. soc. 118 (1996) 100
23. Scholl M., Trnka T.M., Morgan J.P., and Grubbs R.H. Tetrahedron Lett. 40 (1999) 2247
24. Garber S.B., Kingsbury J.S., Gray B.L., and Hoveyda A.H. J. Am. Chem. soc. 122 (2000) 8168
25. Gessler S., Randl S., and Blechert S. Tetrahedron Lett. 41 (2000) 9973
26. Stragies R., and Blechert S. Synlett (1998) 169
27. Zuercher W.J., Hashimoto M., and Grubbs R.H. J. Am. Chem. soc. 118 (1996) 6634
28. Harrity J.P.A., Visser M.0S., Gleason J.D., and Hoveyda A.H. J. Am. Chem. soc. 119 (1997) 1488
29. Burke S.D., Quinn K.J., and Chen V.J. J. Org. Chem. 63 (1998) 8626
30. Ovaa H., van der Marel G.A., van Boom J.H., Stragies R., and Blechert S. Chem. Commun. (2000) 1501
31. Ovaa H., Stapper C., van der Marel G.A., Overkleeft H.S., van Boom J.H., and Blechert S. Tetrahedron 55 (2002) 7503
32. Voigtmann U., and Blechert S. Synthesis (2000) 893
33. Wolczunowicz G., Cocu F.G., and Posternak T. Helv. Chim. Acta 55 (1970) 2275
34. Trost B.M., and Van Vranken D.L. Chem. Rev. 96 (1996) 395
35. Guengerich F.P., DiMari S.J., and Broquist H.P. J. Am. Chem. soc. 95 (1973) 2055
36. Nishimura Y. In: Atta-ur-Rahmany (Ed). Studies in Natural Products Chemistry Vol. 10 (1992), Elsevier, Amsterdam 495-583
37. El Nemr A. Tetrahedron 56 (2000) 8579
38. Zhao H., Hans S., Cheng X., and Mootoo D.R. J. Org. Chem. 6 (2001) 1761
39. de Vincente, J. Trost B.M., and Patterson D.E. Chem. Eur. J. 5 (1999) 3279
40. Arrayas R.G., Canada J., and Carretero J.C. Synlett (2000) 53
41. Buschmann N., Rueckert A., and Blechert S. J. Org. Chem. 67 (2002) 4325
42. Trost B.M., and Patterson D.E. J. Org. Chem. 63 (1998) 1339
43. Van Vranken D.L., and Bingel C. J. Am. Chem. soc. 774 (1992) 9327
44. Mukai C., Sugimoto Y., Miyazawa K., Yamaguchi S., and Hanaoka M. J. Org. Chem. 55 (1998) 6281
45. Kolb H.C., van Niewenhze M.S., and Sharpless K.B. Chem. Rev. 94 (1994) 2483
46. Stragies R., and Blechert S. J. Am. Chem. soc. 722 (2000) 9584
47. Brakman J.C., Daloze D., Pasteels J.M., Van Hecke P., Declercq J.M., Stinwell V., and Francke W. Z. Naturforsch 42c (1987) 627
48. Mitsunobu O. Synthesis (1981) 1
49. Schrock R.R., Murdzek J.S., Bazan G.C., Robbins J., DiMare M., and Oregan M. J. Am. Chem. soc. 112 (1990) 3875
50. Tsuji J. Synthesis (1984) 369
51. Kang S.-K., Jung K.-Y., Chung J.-U., Namkoong E.-Y., and Kim T.-H. J. Org. Chem. 60 (1995) 4678
52. Okazoe T., Takai K., and Utimoto K. J. Am. Chem. soc. 109 (1987) 951
53. Liebermann C. Ber. 22 (1889) 675
54. Liebermann C., and Cybulski G. Ber. 28 (1895) 578
55. Leete E. Phytochemistry 22 (1983) 699
56. Turner C.E., Elsohly M.A., Hanus L., and Elsohly H.N. Phytochemistry 20 (1981) 1403
57. Stapper C., and Blechert S. J. Org. Chem. 67 (2002) 6456
58. Johnson C.R., Golebiowski A., Steensma D.H., and Scialdone M.A. J. Org. Chem. 53 (1993) 7185
59. Johnson C.R., Golebiowski A., and Steensma D.H. J. Am. Chem. soc. 114 (1992) 9414
60. Rother A., Bobbitt J.M., and Schwarting A.E. Chem. Ind. (1962) 654
61. Schwarting A.E., Bobbitt J.M., Rother A., Atal C.K., Khanna K.L., Leary J.D., and Walter W.G. Lloydia 26 (1963) 258
62. Blechert S., and Stapper C. Eur. J. Org. Chem. (2002) 2855
63. Lloyd H.A. Tetrahedron Lett. 50 (1965) 4537
64. Lloyd H.A. Tetrahedron Lett. 22 (1965) 1761
65. Schaudt M., and Blechert S. J. Org. Chem. 68 (2003) 2913
66. Corey E.J., and Eckrich T.M. Tetrahedron Lett. 24 (1983) 3165
67. Singer R.D., and Knöchel R. Chem. Rev. 93 (1993) 2117
68. Ernst M., and Helmchen G. Synthesis 74 (2002) 1953
69. Still W.C., and Mitra A. J. Am. Chem. soc. 100 (1978) 1927
70. Ovaa H., Lastdrager H.B., Codée J.D.C., van der Marel G.A., Overkleeft H.S., and van Boom J.H. J.C.S.Perkin Trans.1 27 (2002) 2370
71. Riether D., and Mulzer J. Org. Lett. 2 (2000) 3139
72. Gerdil R., Liu H., and Bernardineli G. Helv. Chim. Acta (1999) 418
73. Liu W., and Ghosh A.K. J. Org. Chem. 62 (1997) 7908
74. Johnson C.R., and Bis S.J. Tetrahedron Lett. 33 (1992) 7287
75. Staudinger H., and Meyer J. Helv. Chim. Acta 2 (1919) 635
76. Stragies R., and Blechert S. Tetrahedron 55 (1999) 8179
77. Michel K.H., Sandberg F., Haglid F., and Norm T. Acta Pharm. Suecica 4 (1967) 97
78. Daly J.W., and Spande T.F. In: Pelletier S.W. (Ed). Alkaloids: Chemical and Biological Perspectives Vol. 4 (1986), Wiley, New York 1
79. Michael J.P. In: Cordell G.A. (Ed). Alkaloids Vol. 55 (2001), Academic Press, London 92
80. Daly J.W., Garraffo H.M., and Spande T.F. In: Cordell G.A. (Ed). Alkaloids Vol. 43 (1993), Academic Press, London 186
81. Zaminer J., Stapper C., and Blechert S. Tetrahedron Lett. 43 (2002) 6739