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Cycloisomerization of 1,n-Enynes Via Carbophilic Activation

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Computational Mechanisms of Au and Pt Catalyzed Reactions

Part of the book series: Topics in Current Chemistry ((TOPCURRCHEM,volume 302))

Abstract

Metal-catalyzed cycloisomerization of 1,n-enynes has appeared as a highly attractive methodology for the synthesis of original carbo- and heterocycles. This chapter intends to propose an overview of the recent and seminal advances in 1,n-enynes cycloisomerization reactions in the presence of carbophilic transition metals. The recent mechanistic insights, the enantioselective versions, and the applications in total synthesis are highlighted.

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References

  1. Belmont P, Parker E (2009) Eur J Org Chem 35:6075

    Google Scholar 

  2. Lee SI, Chatani N (2009) Chem Commun:371

    Google Scholar 

  3. Jimenez-Nunez E, Echavarren AM (2008) Chem Rev 108:3326

    CAS  Google Scholar 

  4. Michelet V, Toullec PY, Genet J-P (2008) Angew Chem Int Ed 45:7427

    Google Scholar 

  5. Zhang L, Sun J, Kozmin S (2006) Adv Synth Catal 348:2271

    CAS  Google Scholar 

  6. Fairlamb IJS (2004) Angew Chem Int Ed 43:1048

    CAS  Google Scholar 

  7. Lloyd-Jones G (2003) Org Biomol Chem 1:215

    CAS  Google Scholar 

  8. Buisine O, Aubert C, Malacria M (2002) Chem Rev 102:813

    Google Scholar 

  9. Shapiro ND, Toste FD (2010) Synlett 675

    Google Scholar 

  10. Das A, Abu Sohel SM, Liu R-S (2010) Org Biomol Chem 8:860

    Google Scholar 

  11. Abu Sohel SM, Liu R-S (2009) Chem Soc Rev 38:2269

    CAS  Google Scholar 

  12. Furstner A (2009) Chem Soc Rev 38:3208

    Google Scholar 

  13. Arcadi A (2008) Chem Rev 108:3266

    CAS  Google Scholar 

  14. Patil NT, Yamamoto Y (2008) Chem Rev 108:3395

    CAS  Google Scholar 

  15. Li Z, Brouwer C, He C (2008) Chem Rev 108:3239

    CAS  Google Scholar 

  16. Shen HC (2008) Tetrahedron 64:3885

    CAS  Google Scholar 

  17. Skouta R, Li C-J (2008) Tetrahedron 64:4917

    CAS  Google Scholar 

  18. Hashmi ASK, Rudolph M (2008) Chem Soc Rev 37:1766

    CAS  Google Scholar 

  19. Muzart J (2008) Tetrahedron 64:5815

    CAS  Google Scholar 

  20. Gorin DJ, Sherry BD, Toste FD (2008) Chem Rev 108:3351

    CAS  Google Scholar 

  21. Hashmi ASK (2007) Chem Rev 107:3180

    CAS  Google Scholar 

  22. Fürstner A, Davies PW (2007) Angew Chem Int Ed 46:3410

    Google Scholar 

  23. Gorin DJ, Toste FD (2007) Nature 446:395

    CAS  Google Scholar 

  24. Hashmi ASK, Hutchings GJ (2006) Angew Chem Int Ed 45:7896

    Google Scholar 

  25. Jimenez-Nunez E, Echavarren AM (2007) Chem Commun:333

    Google Scholar 

  26. Chianese AR, Lee SJ, Gagné MR (2007) Angew Chem Int Ed 46:4042

    CAS  Google Scholar 

  27. Ma S, Yu S, Gu Z (2006) Angew Chem Int Ed 45:200

    CAS  Google Scholar 

  28. Hashmi ASK (2005) Angew Chem Int Ed 44:6090

    Google Scholar 

  29. Höffmann-Röder A, Krause N (2005) Org Biomol Chem 23:387

    Google Scholar 

  30. Soriano E, Marco-Contelles J (2009) Acc Chem Res 42:1026

    CAS  Google Scholar 

  31. Bongers N, Krause N (2008) Angew Chem Int Ed 47:2178

    CAS  Google Scholar 

  32. Widenhoefer RA (2008) Chem Eur J:5382

    Google Scholar 

  33. Sengupta S, Shi X (2010) Chem Cat Chem 2:609

    CAS  Google Scholar 

  34. Marion N, Nolan SP (2007) Angew Chem Int Ed 46:2750

    CAS  Google Scholar 

  35. Marco-Contelles J, Soriano E (2007) Chem Eur J 13:1350

    CAS  Google Scholar 

  36. Schmidbaur H, Schier A (2010) Organometallics 29:2

    CAS  Google Scholar 

  37. Yukuda Y, Utimoto K (1991) J Org Chem 56:3729

    Google Scholar 

  38. Yukuda Y, Utimoto K (1991) Synthesis:975

    Google Scholar 

  39. Eisenstein O, Hoffmann R (1981) J Am Chem Soc 103:4308

    CAS  Google Scholar 

  40. Shapiro ND, Toste FD (2008) Proc Natl Acad Sci USA 105:2779

    CAS  Google Scholar 

  41. Hooper TN, Green M, Russell CA (2010) Chem Commun 46:2313

    CAS  Google Scholar 

  42. Zuccaccia D, Belpassi L, Rocchigiani L, Tarantelli F, Macchioni A (2010) Inorg Chem 49:3080

    CAS  Google Scholar 

  43. Flügge S, Anoop A, Goddard R, Thiel W, Fürstner A (2009) Chem Eur J 15:8558

    Google Scholar 

  44. Fürstner A, Morency L (2008) Angew Chem Int Ed 47:5030

    Google Scholar 

  45. Hashmi ASK (2008) Angew Chem Int Ed 47:6754

    CAS  Google Scholar 

  46. Eschenmoser A, Ruzicka L, Jeger O, Arigoni D (1955) Helv Chim Acta 38:1890

    CAS  Google Scholar 

  47. Eschenmoser A, Arigoni D (2005) Helv Chim Acta 88:3011

    CAS  Google Scholar 

  48. Stork G, Burgstahler AW (1955) J Am Chem Soc 77:5068

    CAS  Google Scholar 

  49. Schubert U, Ackermann K, Aumann R (1982) Cryst Struct Commun 11:591

    CAS  Google Scholar 

  50. Seidel G, Mynott R, Fürstner A (2009) Angew Chem Int Ed 48:2510

    CAS  Google Scholar 

  51. Benitez D, Shapiro ND, Tkatchouk E, Wang Y, Goddard WA, Toste FD (2009) Nat Chem 1:482

    CAS  Google Scholar 

  52. Fedorov A, Moret M-E, Chen P (2008) J Am Chem Soc 130:8880

    CAS  Google Scholar 

  53. Fedorov A, Chen P (2009) Organometallics 28:1278

    CAS  Google Scholar 

  54. Batiste L, Federov A, Chen P (2010) Chem Commun 46:3899

    CAS  Google Scholar 

  55. Trost BM, Chang VM (1993) Synthesis:824

    Google Scholar 

  56. Chatani N, Morimoto T, Muto T, Murai S (1994) J Am Chem Soc 116:6049

    CAS  Google Scholar 

  57. Chatani N, Furukawa N, Sakurai H, Murai S (1996) Organometallics 15:901

    CAS  Google Scholar 

  58. Fürstner A, Szillat H, Gabor B, Mynott R (1998) J Am Chem Soc 120:8305

    Google Scholar 

  59. Oi S, Tsukamoto I, Miyano S, Inoue Y (2001) Organometallics 20:3704

    CAS  Google Scholar 

  60. Oh CH, Bang SY, Rhim CY (2003) Bull Korean Chem Soc 24:887

    CAS  Google Scholar 

  61. Ota K, Lee SI, Tang J-M, Takachi M, Nakai H, Morimoto T, Sakurai H, Kataoka K, Chatani N (2009) J Am Chem Soc 131:15203

    CAS  Google Scholar 

  62. Chatani N, Inoue H, Morimoto T, Muto T, Murai S (2001) J Org Chem 66:4433

    CAS  Google Scholar 

  63. Nieto-Oberhuber C, Muñoz MP, López S, Jiménez-Núñez E, Nevado C, Herrero-Gómez E, Raducan M, Echavarren AM (2006) Chem Eur J 12:1677

    CAS  Google Scholar 

  64. Nieto-Oberhuber C, Muñoz MP, Buñuel E, Nevado C, Cárdenas DJ, Echavarren AM (2004) Angew Chem Int Ed 43:2402

    CAS  Google Scholar 

  65. Nieto-Oberhuber C, López S, Muñoz MP, Cárdenas DJ, Buñuel E, Nevado C, Echavarren AM (2005) Angew Chem Int Ed 44:6146

    CAS  Google Scholar 

  66. Mezailles N, Ricard L, Gagosz F (2005) Org Lett 7:4133

    CAS  Google Scholar 

  67. Miyanohana Y, Chatani N (2006) Org Lett 8:2155

    CAS  Google Scholar 

  68. Chatani N, Inoue H, Kotsuma T, Murai S (2002) J Am Chem Soc 124:10294

    CAS  Google Scholar 

  69. Nakai H, Chatani N (2007) Chem Lett 36:1494

    CAS  Google Scholar 

  70. Fürstner A, Stelzer F, Szillat H (2001) J Am Chem Soc 123:11863

    Google Scholar 

  71. Nieto-Oberhuber C, López S, Jiménez-Núñez E, Echavarren AM (2006) Chem Eur J 12:5916

    CAS  Google Scholar 

  72. Soriano E, Ballesteros P, Marco-Contelles J (2005) Organometallics 24:3172

    CAS  Google Scholar 

  73. Soriano E, Ballesteros P, Marco-Contelles J (2005) Organometallics 24:3182

    CAS  Google Scholar 

  74. Garcia-Mota M, Cabello N, Maseras F, Echavarren AM, Pérez-Ramirez J, Lopez N (2008) Chem Phys Chem 9:1624

    CAS  Google Scholar 

  75. Cabello N, Jiménez-Núñez E, Buñuel E, Cárdenas DJ, Echavarren AM (2007) Eur J Org Chem:4217

    Google Scholar 

  76. Dankwardt JW (2001) Tetrahedron Lett 42:5809

    CAS  Google Scholar 

  77. Belmont P, Andrez J-C, Allan CSM (2004) Tetrahedron Lett 45:2783

    CAS  Google Scholar 

  78. Shibata T, Ueno Y, Kanda K (2006) Synlett:411

    Google Scholar 

  79. Grisé CM, Barriault L (2006) Org Lett 8:5905

    Google Scholar 

  80. Imase H, Noguchi K, Hirano M, Tanaka K (2008) Org Lett 10:3563

    CAS  Google Scholar 

  81. Cabello N, Rodriguez C, Echavarren AM (2007) Synlett:1753

    Google Scholar 

  82. Bajracharya GB, Nakamura I, Yamamoto Y (2005) J Org Chem 70:892

    CAS  Google Scholar 

  83. Fürstner A, Stelzer F, Szillat H (2000) J Am Chem Soc 122:6785

    Google Scholar 

  84. Trost BM, Doherty GA (2000) J Am Chem Soc 122:3801

    CAS  Google Scholar 

  85. Simmons EM, Hardin AR, Guo X, Sarpong R (2006) Angew Chem Int Ed 47:6650

    Google Scholar 

  86. Simmons EM, Sarpong R (2006) Org Lett 8:2883

    CAS  Google Scholar 

  87. de Jesus CJ, Sarpong R (2010) Org Lett 12:1428

    Google Scholar 

  88. Méndez M, Muñoz MP, Nevado C, Cárdenas DJ, Echavarren AM (2001) J Am Chem Soc 123:10511

    Google Scholar 

  89. Fang S, Wang Z (2009) Eur J Org Chem:5505

    Google Scholar 

  90. Harrak Y, Simonneau A, Malacria M, Gandon V, Fensterbank L (2010) Chem Commun 46:865

    CAS  Google Scholar 

  91. Lee SI, Kim SM, Kim SY, Chung YK (2006) Synlett:2256

    Google Scholar 

  92. Lee SI, Kim SM, Kim SY, Chung YK (2009) Synlett:1355

    Google Scholar 

  93. Comer E, Rohan E, Deng L, Porco JA (2007) Org Lett 9:2123

    CAS  Google Scholar 

  94. Kozak JA, Dake GR (2008) Angew Chem Int Ed 47:4221

    CAS  Google Scholar 

  95. Fernandez-Rivas C, Méndez M, Echavarren AM (2000) J Am Chem Soc 122:1221

    CAS  Google Scholar 

  96. Fernandez-Rivas C, Méndez M, Nieto-Oberhuber C, Echavarren AM (2002) J Org Chem 67:5197

    CAS  Google Scholar 

  97. Porcel S, Echavarren AM (2007) Angew Chem Int Ed 47:2672

    Google Scholar 

  98. Sun J, Conley MP, Zhang L, Kozmin SA (2006) J Am Chem Soc 128:9705

    CAS  Google Scholar 

  99. Zhang L, Kozmin SA (2004) J Am Chem Soc 126:11806

    CAS  Google Scholar 

  100. Boaventura MA, Drouin J, Conia JM (1983) Synthesis:801

    Google Scholar 

  101. Kennedy-Smith JJ, Staben ST, Toste FD (2004) J Am Chem Soc 126:4526

    CAS  Google Scholar 

  102. Staben ST, Kennedy-Smith JJ, Toste FD (2004) Angew Chem Int Ed 43:5350

    CAS  Google Scholar 

  103. Ochida A, Ito H, Sawamura M (2006) J Am Chem Soc 128:16486

    CAS  Google Scholar 

  104. Ito H, Makida Y, Ochida A, Ohmiya H, Sawamura M (2008) Org Lett 10:5051

    CAS  Google Scholar 

  105. Corkey BK, Toste FD (2005) J Am Chem Soc 127:17168

    CAS  Google Scholar 

  106. Binder JT, Crone B, Haug TT, Menz H, Kirsch SF (2008) Org Lett 10:1025

    CAS  Google Scholar 

  107. Montaignac B, Vitale MR, Michelet V, Ratovelomanana-Vidal V (2010) Org Lett 12:2582

    CAS  Google Scholar 

  108. Staben ST, Kennedy-Smith JJ, Huang D, Corkey BK, LaLonde RL, Toste FD (2006) Angew Chem Int Ed 45:5991

    CAS  Google Scholar 

  109. Barabé F, Bétournay G, Bellavance G, Barriault L (2009) Org Lett 11:4236

    Google Scholar 

  110. Corkey BK, Toste FD (2005) J Am Chem Soc 129:2764

    Google Scholar 

  111. Nicolaou KC, Tria GS, Edmonds DJ (2008) Angew Chem Int Ed 47:1783

    Google Scholar 

  112. Blum J, Beer-Krafts H, Badrieh Y (1995) J Org Chem 60:5567

    CAS  Google Scholar 

  113. Nevado C, Ferrer C, Echavarren AM (2004) Org Lett 6:3191

    CAS  Google Scholar 

  114. Ferrer C, Raducan M, Nevado C, Claverie CK, Echavarren AM (2007) Tetrahedron 63:6306

    CAS  Google Scholar 

  115. Mamane V, Gress T, Krause H, Fürstner A (2004) J Am Chem Soc 126:8654

    CAS  Google Scholar 

  116. Harrak Y, Blazykowski C, Bernard M, Cariou K, Mainetti E, Mouriès V, Dhimane AL, Fensterbank L, Malacria M (2004) J Am Chem Soc 126:8656

    CAS  Google Scholar 

  117. Luzung MR, Markham JP, Toste FD (2004) J Am Chem Soc 126:10858

    CAS  Google Scholar 

  118. Freytag M, Ito S, Yoshifuji M (2006) Chem Asian J 1:693

    CAS  Google Scholar 

  119. Soriano E, Ballesteros P, Marco-Contelles J (2004) J Org Chem 69:8018

    CAS  Google Scholar 

  120. He R-X, Li M, Li X-Y (2005) J Mol Struct THEOCHEM 717:21

    CAS  Google Scholar 

  121. Ye L, Chen Q, Zhang J, Michelet V (2009) J Org Chem 74:9550

    CAS  Google Scholar 

  122. Komeyama K, Saigo N, Myiagi M, Takaki K (2009) Angew Chem Int Ed 48:9875

    CAS  Google Scholar 

  123. Horino Y, Yamamoto T, Ueda K, Kuroda S, Toste FD (2009) J Am Chem Soc 131:2809

    CAS  Google Scholar 

  124. Fehr C, Farris I, Sommer H (2006) Org Lett 8:1839

    CAS  Google Scholar 

  125. Fehr C, Winter B, Magpantay I (2009) Chem Eur J 15:9773

    CAS  Google Scholar 

  126. Fehr C, Magpantay I, Arpagaus J, Marquet X, Vuagnoux M (2009) Angew Chem Int Ed 48:7221

    CAS  Google Scholar 

  127. Shibata T, Kobayashi Y, Maekawa S, Toshida N, Takagi K (2005) Tetrahedron 61:9018

    CAS  Google Scholar 

  128. Brissy D, Skander M, Retailleau P, Marinetti A (2007) Organometallics 26:5782

    CAS  Google Scholar 

  129. Brissy D, Skander M, Jullien H, Retailleau P, Marinetti A (2009) Org Lett 11:2137

    CAS  Google Scholar 

  130. Chao C-M, Beltrami D, Toullec PY, Michelet V (2009) Chem Commun:6988

    Google Scholar 

  131. Nishimura T, Kawamoto T, Nagaosa M, Kumamoto H, Hayashi T (2010) Angew Chem Int Ed 49:1638

    CAS  Google Scholar 

  132. Kim SY, Chung YK (2010) J Org Chem 75:1280

    Google Scholar 

  133. Chatani N, Inoue H, Kotsuma T, Murai S (2002) J Am Chem Soc 124:10295

    Google Scholar 

  134. Fürstner A, Davies PW, Gress T (2005) J Am Chem Soc 127:8244

    Google Scholar 

  135. Nieto-Oberhuber C, Pérez-Galán P, Herrero-Gómez E, Lauterbach T, Rodriguez C, López S, Bour C, Rosellón A, Cárdenas DJ, Echavarren AM (2008) J Am Chem Soc 130:269

    CAS  Google Scholar 

  136. Odabachian Y, Gagosz F (2009) Adv Synth Catal 351:379

    CAS  Google Scholar 

  137. Lee YT, Kang YK, Chung YK (2009) J Org Chem 74:7922

    CAS  Google Scholar 

  138. Marion F, Coulomb C, Courillon C, Fensterbank L, Malacria M (2004) Org Lett 6:1509

    CAS  Google Scholar 

  139. Marion F, Coulomb J, Servais A, Courillon C, Fensterbank L, Malacria M (2006) Tetrahedron 62:3856

    CAS  Google Scholar 

  140. Couty S, Meyer C, Cossy J (2006) Angew Chem Int Ed 45:6726

    CAS  Google Scholar 

  141. Couty S, Meyer C, Cossy J (2009) Tetrahedron 65:1809

    CAS  Google Scholar 

  142. Soriano E, Marco-Contelles J (2005) J Org Chem 70:9345

    CAS  Google Scholar 

  143. Tenaglia A, Gaillard S (2008) Angew Chem Int Ed 47:2454

    CAS  Google Scholar 

  144. Fürstner A, Stimson CC (2007) Angew Chem Int Ed 46:8845

    Google Scholar 

  145. Kim SY, Park Y, Chung YK (2010) Angew Chem Int Ed 49:415

    CAS  Google Scholar 

  146. Kirsch SF, Binder JT, Crone B, Duschek A, Haug TT, Liébert C, Menz H (2007) Angew Chem Int Ed 46:2310

    CAS  Google Scholar 

  147. Sethofer SG, Staben ST, Hung OY, Toste FD (2008) Org Lett 10:4315

    CAS  Google Scholar 

  148. Galland JC, Savignac M, Genêt JP (1997) Tetrahedron Lett 38:8695

    CAS  Google Scholar 

  149. Galland JC, Dias S, Savignac M, Genêt JP (2001) Tetrahedron 57:5137

    CAS  Google Scholar 

  150. Charruault L, Michelet V, Genêt JP (2002) Tetrahedron Lett 43:4757

    CAS  Google Scholar 

  151. Méndez M, Muñoz MP, Echavarren AM (2000) J Am Chem Soc 122:11549

    Google Scholar 

  152. Nevado C, Cárdenas DJ, Echavarren AM (2003) Chem Eur J 9:2627

    CAS  Google Scholar 

  153. Nishizawa M, Yadav VK, Skwarczynski M, Takao H, Imagawa H, Sugihara T (2003) Org Lett 5:1609

    CAS  Google Scholar 

  154. Faller JW, Fontaine PP (2006) J Organomet Chem 691:1912

    CAS  Google Scholar 

  155. Nieto-Oberhuber C, Paz Muñoz M, Bunuel E, Nevado C, Cardenas DJ, Echavarren AM (2005) Angew Chem Int Ed 44:6146

    CAS  Google Scholar 

  156. Genin E, Leseurre, Toullec PY, Genêt J-P, Michelet V (2007) Synlett:1780

    Google Scholar 

  157. Chao C-M, Toullec PY, Michelet V (2009) Tetrahedron Lett 50:3719

    CAS  Google Scholar 

  158. Sethofer SG, Mayer T, Toste FD (2010) J Am Chem Soc 132:8276

    CAS  Google Scholar 

  159. Zhang L, Kozmin SA (2005) J Am Chem Soc 127:6962

    CAS  Google Scholar 

  160. Sherry BD, Maus L, Laforzeta BN, Toste FD (2006) J Am Chem Soc 128:8132

    CAS  Google Scholar 

  161. Buzas AK, Istrate FM, Gagosz F (2007) Angew Chem Int Ed 46:1141

    CAS  Google Scholar 

  162. Toullec PY, Blarre T, Michelet V (2009) Org Lett 11:2888

    CAS  Google Scholar 

  163. Li G, Liu Y (2010) J Org Chem 75:2903

    CAS  Google Scholar 

  164. Nevado C, Charuault L, Michelet V, Nieto-Oberhuber C, Muñoz MP, Méndez M, Rager M-N, Genêt J-P, Echavarren AM (2003) Eur J Org Chem:706

    Google Scholar 

  165. Baumgarten S, Lesage D, Gandon V, Goddard J-P, Malacria M, Tabet J-C, Gimbert Y, Fensterbank L (2010) Chem Cat Chem 1:138

    Google Scholar 

  166. Nelsen DL, Gagné MR (2009) Organometallics 28:950

    CAS  Google Scholar 

  167. Charruault L, Michelet V, Taras R, Gladiali S, Genêt JP (2004) Chem Commun:850

    Google Scholar 

  168. Gladiali S, Alberico E (2008) In: Börner A (ed) Trivalent phosphorus compounds in asymmetric catalysis: synthesis and applications, vol 2. Wiley-VCH, Weinheim, p 177

    Google Scholar 

  169. Toullec PY, Michelet V (2010) Curr Org Chem 14:1245

    Google Scholar 

  170. Gladiali S, Toullec PY, Genêt J-P, Michelet V (2011) Electronic encyclopedia of reagents for organic synthesis. Wiley, New York

    Google Scholar 

  171. Muñoz MP, Adrio J, Carretero JC, Echavarren AM (2005) Organometallics 24:1293

    Google Scholar 

  172. Martinez A, Garcia-Garcia P, Fernandez-Rodriguez MA, Rodriguez F, Sanz R (2010) Angew Chem Int Ed 49:4633

    CAS  Google Scholar 

  173. Chao C-M, Genin E, Toullec PY, Genêt JP, Michelet V (2009) J Organomet Chem 694:538

    CAS  Google Scholar 

  174. Matsumoto Y, Selim KB, Nakanishi H, Yamada K-I, Yamamoto Y, Tomioka K (2010) Tetrahedron Lett 51:404

    CAS  Google Scholar 

  175. Jiménez-Núñez E, Claverie CK, Nieto-Oberhuber C, Echavarren AM (2006) Angew Chem Int Ed 45:5452

    Google Scholar 

  176. Escribano-Cuesta A, López-Carillo V, Janssen D, Echavarren AM (2009) Chem Eur J 15:5646

    CAS  Google Scholar 

  177. Schelwies M, Dempwolff AL, Rominger F, Helmchen G (2007) Angew Chem Int Ed 46:5598

    Google Scholar 

  178. Schelwies M, Moser R, Dempwolff AL, Rominger F, Helmchen G (2009) Chem Eur J 15:10888

    CAS  Google Scholar 

  179. Jiménez-Núñez E, Molawi K, Echavarren AM (2009) Chem Commun:7327

    Google Scholar 

  180. Molawi K, Delpont N, Echavarren AM (2010) Angew Chem Int Ed 49:3517

    CAS  Google Scholar 

  181. Zhou Q, Chen X, Ma D (2010) Angew Chem Int Ed 49:3513

    CAS  Google Scholar 

  182. Witham CA, Mauleón P, Shapiro ND, Sherry BD, Toste FD (2007) J Am Chem Soc 129:5838

    CAS  Google Scholar 

  183. Chatani N, Kataoka K, Murai S, Furukawa N, Seki Y (1998) J Am Chem Soc 120:9104

    CAS  Google Scholar 

  184. Mainetti E, Mouries V, Fensterbank L, Malacria M, Marco-Contelles J (2002) Angew Chem Int Ed 41:2132

    CAS  Google Scholar 

  185. Marco-Contelles J, Soriano E (2006) J Mol Struct THEOCHEM 761:45

    CAS  Google Scholar 

  186. Nieto-Oberhuber C, López S, Muñoz MP, Jiménez-Núñez E, Buñuel E, Cárdenas DJ, Echavarren AM (2006) Chem Eur J 12:1694

    CAS  Google Scholar 

  187. Jiménez-Núñez E, Raducan M, Lauterbach T, Molawi K, Solorio CR, Echavarren AM (2009) Angew Chem Int Ed 48:6152

    Google Scholar 

  188. Kim SM, Park JH, Choi SY, Chung YK (2007) Angew Chem Int Ed 46:6172

    CAS  Google Scholar 

  189. Sim SH, Lee SI, Park JH, Chung YK (2010) Adv Synth Catal 352:317

    CAS  Google Scholar 

  190. López S, Herrero-Gómez E, Pérez-Galán P, Nieto-Oberhuber C, Echavarren AM (2006) Angew Chem Int Ed 45:6029

    Google Scholar 

  191. Nieto-Oberhuber C, López S, Echavarren AM (2005) J Am Chem Soc 127:6178

    CAS  Google Scholar 

  192. Yeh M-CP, Tsao W-C, Lee B-J, Lin T-L (2008) Organometallics 27:5326

    CAS  Google Scholar 

  193. Toullec PY, Genin E, Leseurre E, Genêt JP, Michelet V (2006) Angew Chem Int Ed 45:7427

    CAS  Google Scholar 

  194. Amijs CHM, Ferrer C, Echavarren AM (2007) Chem Commun:698

    Google Scholar 

  195. Amijs CHM, López-Carrillo V, Raducan M, Pérez-Galán P, Ferrer C, Echavarren AM (2008) J Org Chem 73:7721

    CAS  Google Scholar 

  196. Leseurre L, Chao C-M, Seki T, Genin E, Toullec PY, Genet J-P, Michelet V (2009) Tetrahedron 65:1911

    CAS  Google Scholar 

  197. Nieto-Oberhuber C, Pérez-Galán P, Herrero-Gómez E, Lauterbach T, Rodríguez C, López S, Bour C, Rosellón A, Cárdenas DJ, Echavarren AM (2008) J Am Chem Soc 130:269

    CAS  Google Scholar 

  198. Harrison TJ, Patrick BO, Dake GR (2007) Org Lett 9:367

    CAS  Google Scholar 

  199. Kozak JA, Dodd JM, Harrison TJ, Jardine KJ, Patrick BO, Dake GR (2009) J Org Chem 74:6929

    CAS  Google Scholar 

  200. Imagawa H, Iyenaga T, Nishizawa M (2005) Org Lett 7:451

    CAS  Google Scholar 

  201. Imagawa H, Iyenaga T, Nishizawa M (2005) Synlett:703

    Google Scholar 

  202. Nishizawa N, Imagawa H, Yamamoto H (2010) Org Biomol Chem 8:511

    CAS  Google Scholar 

  203. Toullec PY, Chao C-M, Chen Q, Gladiali S, Genêt J-P, Michelet V (2008) Adv Synth Catal 350:2401

    CAS  Google Scholar 

  204. Chao C-M, Vitale MR, Toullec PY, Genêt J-P, Michelet V (2009) Chem Eur J 15:1319

    CAS  Google Scholar 

  205. Leseurre L, Toullec PY, Genêt J-P, Michelet V (2007) Org Lett 9:4049

    CAS  Google Scholar 

  206. Böhringer S, Gagosz F (2008) Adv Synth Catal 350:2617

    Google Scholar 

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Toullec, P.Y., Michelet, V. (2011). Cycloisomerization of 1,n-Enynes Via Carbophilic Activation. In: Soriano, E., Marco-Contelles, J. (eds) Computational Mechanisms of Au and Pt Catalyzed Reactions. Topics in Current Chemistry, vol 302. Springer, Berlin, Heidelberg. https://doi.org/10.1007/128_2010_116

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