Complex polycyclic molecules from acyclic precursors via transition metal-catalyzed cascade reactions

Topics in Organometallic Chemistry

Volumn 19, Issue , 2006, Pages 259-294

  Aubert, Corinne ^a   Fensterbank, Louis ^a   Gandon, Vincent ^a   Malacria, Max ^a  

^a SORBONNE UNIVERSITÉ   (France)

Author keywords

Carbenoid; Cascade; Cycloaddition; Cycloisomerization; Skeletal rearrangement

Indexed keywords

EID: 33845435469     PISSN: 14366002     EISSN: None     Source Type: Book Series    
DOI: 10.1007/3418_011     Document Type: Review

References (99)

1. Malacria M (1996) Chem Rev 96:289
2. Tietze LF, Haunert F (2000) In: Vögtle F, Stoddart JF, Shibasaki M (eds) Stimulating concepts in chemistry. Wiley, Weinheim, p 39
3. Padwa A, Weingarten MD (1996) Chem Rev 96:223
4. de Kimpe N (1996) In: Katritzky AR, Rees CW, Scriven EFV, Padwa A (eds) Comprehensive heterocyclic chemistry II, vol 1. Pergamon, New York, p 507
5. Zhang TY, Hatfield LD (1996) In: Katritzky AR, Rees CW, Scriven EFV, Padwa A (eds) Comprehensive heterocyclic chemistry II, vol 1. Pergamon, New York, p 591
6. Jastrzebski JTBH, van Koten G (1996) In: Katritzky AR, Rees CW, Scriven EFV, Padwa A (eds) Comprehensive heterocyclic chemistry II, vol 1. Pergamon, New York, p 623
7. Page MI (ed) (1992) The chemistry of β-lactams. Blackie, Glasgow
8. Bruggink A (ed) (2001) Synthesis of β-lACTAMS aNtibiotics. Kluwer, Dordrecht
9. Marco-Contelles J (2004) Angew Chem Int Ed 43:2198
10. Gomez-Gallego M, Manchero MJ, Sierra MA (2000) Tetrahedron 56:5743
11. Ghiron C, Rossi T (1997) Targets Heterocycl Syst 1:161
12. Biondi S (1997) Spec Publ R Soc Chem 198:86
13. Perboni A, Tamburini B, Rossi T, Donati D, Tarzia G, Gaviraghi G (1993) Spec Publ R Soc Chem 119:21
14. Kinugasa M, Hashimoto S (1972) J Chem Soc Chem Commun: 466
15. Miura M, Enna M, Okuro K, Nomura M (1995) J Org Chem 60:4999
16. Shintani R, Fu GC (2003) Angew Chem Int Ed 42:4082
17. van Beek TA, de Groot A (1986) Recl Trav Chim Pays-Bas 105:513
18. Schuda P (1980) Top Curr Chem 91:75
19. Minto RE, Townsend CA (1997) Chem Rev 97:2537
20. Roggenbuck R, Schmidt A, Eilbracht P (2002) Org Lett 4:289
21. Eilbracht P, Bärfacker L, Buss C, Hollmann C, Kitsos-Rzychon BE, Kranemann CL, Rische T, Roggenbuck R, Schmidt A (1999) Chem Rev 99:3329
22. Ashfeld BL, Miller KA, Martin SF (2004) Org Lett 6:1321
23. Bonaga LVR, Krafft ME (2004) Tetrahedron 60:9795
24. Brummond KM, Kent JL (2000) Tetrahedron 56:3263
25. Wender PA, Husfeld CO, Langkopf E, Love JA, Pleuss N (1998) Tetrahedron 54:7203
26. Ashfeld BL, Miller KA, Smith AJ, Tran K, Martin SF (2005) Org Lett 7:1661
27. Evans PA, Robinson JE (2001) J Am Chem Soc 123:4609
28. Jeong N, Seo SD, Shin JY (2000) J Am Chem Soc 122:10220
29. Lautens M, Klute W, Tam W (1996) Chem Rev 96:49
30. Ojima I, Tzamarioudaki M, Li Z, Donovan RJ (1996) Chem Rev 96:635
31. Eichberg MJ, Dorta RL, Grotjahn DB, Lamottke K, Schmidt M, Vollhardt KPC (2001) J Am Chem Soc 123:9324
32. Carruthers W (1990) In: Baldwin JE, Magnus PD (eds) Cycloaddition reactions in organic synthesis. Tetrahedron organic chemistry series, vol 8. Pergamon, Oxford
33. Yamamoto Y, Kitahara H, Ogawa R, Kawaguchi H, Tatsumi K, Itoh K (2000) J Am Chem Soc 122:4310
34. Odedra A, Wu C-J, Madhushaw RJ, Wang S-L, Liu R-S (2003) J Am Chem Soc 125:9610
35. Theobald BJ (2002) Tetrahedron 58:4133
36. Quintal MM, Closser KD, Shea KM (2004) Org Lett 6:4949
37. Son SU, Choi MR, Chung YK, Lee S-G (2000) Org Lett 2:2097
38. Ojima I (2002) Pure Appl Chem 74:159
39. Ojima I, Vu AT, McCullagh JV, Kinoshita A (1999) J Am Chem Soc 121:3230
40. Mahandru GM, Skauge ARL, Chowdhury SK, Amarasinghe KKD, Heeg MJ, Montgomery J (2003) J Am Chem Soc 125:13481
41. Kande KD, Amarasinghe KKD, Chowdhury SK, Heeg MJ, Montgomery J (2001) Organometallics 20:370
42. Thommen M, Keese R (1997) Synlett: 231
43. Thommen M, Veretenov A, Guidetti-Grept R, Keese R (1996) Helv Chim Acta 79:461
44. Kim DH, Son SU, Chung YK, Lee S-G (2002) Chem Commun: 56
45. Hong SH, Kim JW, Choi DS, Chung YK, Lee S-G (1999) Chem Commun: 2099
46. Lee SI, Son SU, Choi MR, Chung YK, Lee S-G (2003) Tetrahedron Lett 44:4705
47. Brummond KM, You L (2005) Tetrahedron 61:6180
48. Funk RL, Vollhardt KPC (1980) J Am Chem Soc 102:5253
49. Cruciani P, Stammler R, Aubert C, Malacria M (1996) J Org Chem 61:2699
50. Cruciani P, Aubert C, Malacria M (1996) Synlett: 105
51. Doyle MP (1995) In: Abel EW, Stone FGA, Wilkinson G, Hegedus L (eds) Comprehensive organometallic chemistry II, vol 12. Pergamon, Oxford, p 387
52. Gillon A, Ovadia D, Kapon M, Bien S (1982) Tetrahedron 38:1477
53. Dauben WG, Dinges J, Smith TC (1993) J Org Chem 58:7635
54. Chiu P, Chen B, Cheng KF (2001) Org Lett 3:1721
55. Chen B, Ko RYY, Yuen MSM, Cheng K-F, Chiu P (2003) J Org Chem 68:4195
56. Graening T, Friedrichsen W, Lex J, Schmalz H-G (2002) Angew Chem Int Ed 41:1524
57. Hodgson DM, Brückl T, Glen R, Labande AH, Selden DA, Dossetter AG, Redgrave AJ (2004) Proc Natl Acad Sci USA 101:5450
58. Padwa A, Krumpe KE, Gareau Y, Chiacchio U (1991) J Org Chem 56:2523
59. Monnier F, Castillo D, Dérien S, Toupet L, Dixneuf PH (2003) Angew Chem Int Ed 42:5474
60. Ni Y, Montgomery J (2004) J Am Chem Soc 126:11162
61. McDonald FE, Reddy KS, Diaz Y (2000) J Am Chem Soc 122:4304
62. Barluenga J, Diéguez A, Rodriguez F, Florez J, Fananas FJ (2002) J Am Chem Soc 124:9056
63. Barluenga J, Dieguez A, Rodriguez F, Fananas FJ (2005) Angew Chem Int Ed 44:126
64. Monteiro N, Balme G (2000) J Org Chem 65:3223
65. Chisholm MH, Clark HC (1973) Acc Chem Res 6:202
66. Trost BM, Tanoury GJ (1988) J Am Chem Soc 110:1636
67. Trost BM, Trost MK (1991) J Am Chem Soc 113:1850
68. Trost BM, Chang VK (1993) Synthesis: 824
69. Trost BM, Hashmi ASK (1993) Angew Chem Int Ed Engl 32:1085
70. Trost BM, Hashmi ASK (1994) J Am Chem Soc 116:2183
71. Chatani N, Morimoto T, Muto T, Murai S (1994) J Am Chem Soc 116:6049
72. Pilette D, Moreau S, Le Bozec H, Dixneuf PH, Corrigan JF, Carty AJ (1994) Chem Commun: 409
73. Blum J, Beer-Kraft H, Badrieh Y (1995) J Org Chem 60:5567
74. Bruneau C (2005) Angew Chem Int Ed 44:2328
75. Chatani N, Furukawa N, Sakurai H, Murai S (1996) Organometallics 15:901
76. Méndez M, Mamane V, Fürstner A (2003) Chemtracts-Org Chem 16:397
77. Añorbe L, Domínguez G, Pérez-Castells J (2004) Chem Eur J 10:4938
78. Echavarren AM, Nevado C (2004) Chem Soc Rev 33:431
79. Fürstner A, Szillat H, Gabor B, Mynott R (1998) J Am Chem Soc 120:8305
80. Trost BM, Doherty GA (2000) J Am Chem Soc 122:3801
81. Chatani N, Kataoka K, Murai S, Furukawa N, Seki Y (1998) J Am Chem Soc 120:9104
82. Mainetti E, Mouriès V, Fensterbank L, Malacria M, Marco-Contelles J (2002) Angew Chem Int Ed 41:2132
83. Rautenstrauch V (1984) J Org Chem 49:950
84. Mamane V, Gress T, Krause H, Fürstner A (2004) J Am Chem Soc 126:8654
85. Harrak Y, Blaszykowski C, Bernard M, Cariou K, Mainetti E, Mouriès V, Dhimane AL, Fensterbank L, Malacria M (2004) J Am Chem Soc 126:8656
86. Cariou K, Mainetti E, Fensterbank L, Malacria M (2004) Tetrahedron 60:9745
87. Anjum S, Marco-Contelles J (2005) Tetrahedron 61:4793
88. Fürstner A, Hannen P (2004) Chem Commun: 2546
89. Peppers BP, Diver ST (2004) J Am Chem Soc 126:9524
90. Diver ST, Giessert AJ (2004) Chem Rev 104:1317
91. Nieto-Oberhuber C, Paz Muñoz M, Buñuel E, Nevado C, Cárdenas DJ, Echavarren AM (2004) Angew Chem Int Ed 43:2402
92. Luzung MR, Markham JP, Toste FD (2004) J Am Chem Soc 126:10858
93. Zhang L, Kozmin SA (2005) J Am Chem Soc 127:6962
94. Kusama H, Yamabe H, Onizawa Y, Hoshino T, Iwasawa N (2005) Angew Chem Int Ed 44:468
95. Miki K, Nishino F, Ohe K, Uemura S (2002) J Am Chem Soc 124:5260
96. Nishino F, Miki K, Kato H, Ohe K, Uemura S (2003) Org Lett 5:2615
97. Nishibayashi Y, Yoshikawa E, Inada Y, Hidai M, Uemura S (2004) J Am Chem Soc 126:16066
98. Cadran N, Cariou K, Hervé G, Aubert C, Fensterbank L, Malacria M, Marco-Contelles J (2004) J Am Chem Soc 126:3408
99. Nishizawa M, Yadav VK, Skwarczynski M, Takao H, Imagawa H, Sugihara T (2003) Org Lett 5:1609