Advertisement

Catalysis Letters

, Volume 149, Issue 6, pp 1513–1559 | Cite as

Synthesis of Six-Membered N-Heterocycles Using Ruthenium Catalysts

  • Navjeet KaurEmail author
Article
  • 34 Downloads

Abstract

A wide variety of biological activities are possessed by nitrogen, oxygen, and sulfur containing heterocycles and many methods are explored for the preparation of these heterocyclic compounds. Metal catalysts worked with high activity in organic reactions. The synthesis of heterocycles with the help of metal catalysts became very important in organic synthesis. New protocols have been investigated for the synthesis of heterocycles in the last decades. This article mainly focused on the synthesis of six-membered N-heterocylces in the presence of ruthenium catalyst.

Graphical Abstract

Keywords

Ruthenium Catalysis Nitrogen heterocycles Grubs catalyst RCM Asymmetric synthesis 

Notes

Compliance with Ethical Standards

Conflict of interest

The authors declare no conflict of interest.

References

  1. 1.
    Balaban AT, Oniciu DC, Katritzky AR (2004) Chem Rev 104:2777Google Scholar
  2. 2.
    Majumdar P, Pati A, Patra M, Behera RK, Behera AK (2014) Chem Rev 114:2942Google Scholar
  3. 3.
    Majumdar KC, Chattopadhyay B, Ray K (2010) Curr Org Synth 7:153Google Scholar
  4. 4.
    Compain P (2007) Adv Synth Catal 349:1829Google Scholar
  5. 5.
    Pellissier H (2013) Chem Rev 113:442Google Scholar
  6. 6.
    Martins MAP, Cunico W, Pereira CMP, Flores AFC, Bonacorso HG, Zanatta N (2004) Curr Org Synth 1:391Google Scholar
  7. 7.
    Kaur N (2015) Catal Rev 57:478Google Scholar
  8. 8.
    Domling A (2006) Chem Rev 106:17Google Scholar
  9. 9.
    Kaur N (2015) J Heterocycl Chem 52:953Google Scholar
  10. 10.
    Kaur N (2017) Curr Org Synth 14:531Google Scholar
  11. 11.
    Kaur N (2017) Curr Org Synth 14:972Google Scholar
  12. 12.
    Kaur N (2017) Mini Rev Org Chem 14:3Google Scholar
  13. 13.
    Kaur N (2016) Synth React Inorg Met Org Nano-Met Chem 46:983Google Scholar
  14. 14.
    Kaur N (2017) Inorg Nano-Met Chem 47:163Google Scholar
  15. 15.
    Orru RVA, de Greef M (2003) Synthesis 10:1471Google Scholar
  16. 16.
    Kaur N (2018) Synth Commun 48:1551Google Scholar
  17. 17.
    Kaur N (2018) Synth Commun 48:1588Google Scholar
  18. 18.
    Kaur N (2018) Synth Commun 48:1715Google Scholar
  19. 19.
    Kaur N (2018) Synth Commun 48:2119Google Scholar
  20. 20.
    Kaur N (2018) Synth Commun 48:2715Google Scholar
  21. 21.
    Kaur N (2018) Synth Commun 48:2935Google Scholar
  22. 22.
    Kaur N (2018) Synth Commun 48:2815Google Scholar
  23. 23.
    Kaur N (2018) Inorg Chem Commun 99:82Google Scholar
  24. 24.
    Kaur N (2014) Inorg Chem Commun 49:86Google Scholar
  25. 25.
    Kaur N, Kishore D (2014) Synth Commun 44:1173Google Scholar
  26. 26.
    Kaur N, Kishore D (2014) Synth Commun 44:1019Google Scholar
  27. 27.
    Kaur N (2014) Synth Commun 44:3483Google Scholar
  28. 28.
    Kaur N (2014) Synth Commun 44:3509Google Scholar
  29. 29.
    Kaur N (2014) Synth Commun 44:3229Google Scholar
  30. 30.
    Kaur N (2018) Synth Commun 48:1235Google Scholar
  31. 31.
    Kaur N (2018) Synth Commun 48:1259Google Scholar
  32. 32.
    Kaur N (2018) J Sulfur Chem 39:544Google Scholar
  33. 33.
    Kaur N (2015) J Iran Chem Soc 12:9Google Scholar
  34. 34.
    Kaur N (2015) Synth Commun 45:1269Google Scholar
  35. 35.
    Kaur N (2015) Synth Commun 45:1379Google Scholar
  36. 36.
    Kaur N (2014) Synth Commun 44:3201Google Scholar
  37. 37.
    Kaur N (2015) Synth Commun 45:1Google Scholar
  38. 38.
    Kaur N (2015) Synth Commun 45:35Google Scholar
  39. 39.
    Kaur N (2018) Curr Org Synth 15:940Google Scholar
  40. 40.
    Kaur N (2018) Synth Commun 48:2457Google Scholar
  41. 41.
    Kaur N (2015) Synth Commun 45:789Google Scholar
  42. 42.
    Kaur N (2015) Synth Commun 45:151Google Scholar
  43. 43.
    Kaur N (2015) Synth Commun 45:173Google Scholar
  44. 44.
    Kaur N (2015) Synth Commun 45:273Google Scholar
  45. 45.
    Kaur N (2015) Synth Commun 45:300Google Scholar
  46. 46.
    Kaur N, Kishore D (2014) Synth Commun 44:1375Google Scholar
  47. 47.
    Kaur N (2015) Synth Commun 45:909Google Scholar
  48. 48.
    Kaur N (2015) Synth Commun 45:432Google Scholar
  49. 49.
    Kaur N (2014) J Iran Chem Soc 11:523Google Scholar
  50. 50.
    Kaur N (2015) Synth Commun 45:1145Google Scholar
  51. 51.
    Kaur N (2015) Synth Commun 45:1493Google Scholar
  52. 52.
    Kaur N (2015) Synth Commun 45:1599Google Scholar
  53. 53.
    Kaur N (2015) Synth Commun 45:1711Google Scholar
  54. 54.
    Patil NT, Yamamoto Y (2008) Chem Rev 108:3395Google Scholar
  55. 55.
    Kaur N (2015) Synth Commun 45:403Google Scholar
  56. 56.
    Kaur N (2015) Synth Commun 45:539Google Scholar
  57. 57.
    Kaur N, Kishore D (2014) Synth Commun 44:2577Google Scholar
  58. 58.
    Kaur N, Kishore D (2014) Synth Commun 44:2615Google Scholar
  59. 59.
    Kaur N, Kishore D (2014) Synth Commun 44:2739Google Scholar
  60. 60.
    Alberico D, Scott ME, Lautens M (2007) Chem Rev 107:174Google Scholar
  61. 61.
    Kaur N (2017) Curr Organocatal 4:122Google Scholar
  62. 62.
    Dick AR, Sanford MS (2006) Tetrahedron 62:2439Google Scholar
  63. 63.
    Kaur N (2015) Catal Rev 57:1Google Scholar
  64. 64.
    Kaur N, Kishore D (2014) Synth Commun 44:3082Google Scholar
  65. 65.
    Kaur N, Kishore D (2014) Synth Commun 44:3047Google Scholar
  66. 66.
    Nakamura I, Yamamoto Y (2004) Chem Rev 104:2127Google Scholar
  67. 67.
    Zeni G, Larock RC (2006) Chem Rev 106:4644Google Scholar
  68. 68.
    Jimenez-Gonzalez L, Garcia-Munoz S, Alvarez-Corral M, Munoz-Dorado M, Rodriguez-Garcia I (2006) Chem Eur J 12:8762Google Scholar
  69. 69.
    Li Z, He C (2006) Eur J Org Chem 19:4313Google Scholar
  70. 70.
    Claesson A, Sahlberg C, Luthman K (1979) Acta Chem Scand B 33:309Google Scholar
  71. 71.
    Claesson A, Olsson LI (1979) Synthesis 9:743Google Scholar
  72. 72.
    Hunt JCA, Laurent P, Moody CJ (2002) J Chem Soc Perkin Trans 1 21:2378Google Scholar
  73. 73.
    Bates RW, Boonsombat J, Lu Y, Nemeth JA, Sa-Ei K, Song P, Cai MP, Cranwell PB, Winbush S (2008) Pure Appl Chem 80:681Google Scholar
  74. 74.
    Kotha S, Singh K (2004) Tetrahedron Lett 45:9607Google Scholar
  75. 75.
    Banafi L, Guanti G, Paravidino M, Riva R (2005) Org Biomol Chem 3:1729Google Scholar
  76. 76.
    Majumdar KC, Muhuri S, Islam RU, Chattopadhyay B (2009) Heterocycles 78:1109Google Scholar
  77. 77.
    Miller SI, Blackwell HE, Grubbs RH (1996) J Am Chem Soc 118:9606Google Scholar
  78. 78.
    van den Nieuwendijk AMCH, Ghisaidoobe ABT, Overkleeft HS, Brussee J, van der Gen A (2004) Tetrahedron 60:10385Google Scholar
  79. 79.
    Krafft ME, Song EH, Davoile RJ (2005) Tetrahedron Lett 46:6359Google Scholar
  80. 80.
    Matteis VD, van Delft FL, Jakobi H, Lindell S, Tiebes J, Rutjes FPJT (2006) J Org Chem 71:7527Google Scholar
  81. 81.
    Chang MY, Kung YH, Chen ST (2006) Tetrahedron 62:10843Google Scholar
  82. 82.
    Hercouet A, Baudet C, Carboni B (2004) Tetrahedron Lett 45:8749Google Scholar
  83. 83.
    Mori M, Wakamatsu H, Saito N, Sato Y, Narita R, Sato Y, Fujita R (2006) Tetrahedron 62:3872Google Scholar
  84. 84.
    Fustero S, Sanchez-Rosello M, Jimenez D, Sanz-Cervera JF, del Pozo C, Acena JL (2006) J Org Chem 71:2706Google Scholar
  85. 85.
    Hong SH, Day MW, Grubbs RH (2004) J Am Chem Soc 126:7414Google Scholar
  86. 86.
    Marhold M, Buer A, Hiemstra H, van Maarseveen JH, Haufe G (2004) Tetrahedron Lett 45:57Google Scholar
  87. 87.
    Chaterjee AK, Morgan JP, Scholl M, Grubbs RH (2000) J Am Chem Soc 122:3783Google Scholar
  88. 88.
    Chao W, Meketa ML, Weinreb SM (2004) Synthesis 12:2058Google Scholar
  89. 89.
    Yamaguchi R, Fujita KI, Zhu M (2010) Heterocycles 81:1093Google Scholar
  90. 90.
    Hesp KD, Stradiotto M (2010) Chem Cat Chem 2:1192Google Scholar
  91. 91.
    Xie JH, Zhu SF, Zhou QL (2011) Chem Rev 111:1713Google Scholar
  92. 92.
    Bahn S, Imm S, Neubert L, Zhang M, Neumann H, Beller M (2011) Chem Cat Chem 3:1853Google Scholar
  93. 93.
    Kallstrom S, Leino R (2008) Bioorg Med Chem 16:601Google Scholar
  94. 94.
    Cody WL, Holsworth DD, Powell NA, Jalaie M, Zhang E, Wang W, Samas B, Bryant J, Ostroski R, Ryan MJ, Edmunds JJ (2005) Bioorg Med Chem 13:59Google Scholar
  95. 95.
    Hu XE, Kim NK, Gray JL, Almstead JIK, Seibel WL, Ledoussal B (2003) J Med Chem 46:3656Google Scholar
  96. 96.
    Petukhov PA, Zhang J, Wang CZ, Ye YP, Johnson KM, Kozikowski AP (2004) J Med Chem 47:3009Google Scholar
  97. 97.
    Trost BM, Krische MJ (1998) Synlett 1:1Google Scholar
  98. 98.
    Aubert C, Buisine O, Malacria M (2002) Chem Rev 102:813Google Scholar
  99. 99.
    Zhang Z, Zhu G, Tong X, Wang F, Xie X, Wang J, Liang L (2006) Curr Org Chem 10:1457Google Scholar
  100. 100.
    Imamoglu Y, Dragutan V (2007) Springer 375Google Scholar
  101. 101.
    Michelet V, Toullec PY, Genet JP (2008) Angew Chem Int Ed 47:4268Google Scholar
  102. 102.
    Lee SI, Chatani N (2009) Chem Commun 4:371Google Scholar
  103. 103.
    Furstner A, Stelzer F, Szillat H (2001) J Am Chem Soc 123:11863Google Scholar
  104. 104.
    Hatano M, Mikami K (2003) J Am Chem Soc 125:4704Google Scholar
  105. 105.
    Trost BM, Surivet JP, Toste FD (2004) J Am Chem Soc 126:15592Google Scholar
  106. 106.
    Shibata T, Kobayashi Y, Maekawa S, Toshida N, Takagi K (2005) Tetrahedron 61:9018Google Scholar
  107. 107.
    Trost BM, Martinez J, Kulawiec RJ, Indolese AF (1993) J Am Chem Soc 115:10402Google Scholar
  108. 108.
    Trost BM, Indolese AF (1993) J Am Chem Soc 115:4361Google Scholar
  109. 109.
    Trost BM, Indolese AF, Muller TJJ, Treptow B (1995) J Am Chem Soc 117:615Google Scholar
  110. 110.
    Trost BM, Muller TJJ, Martinez J (1995) J Am Chem Soc 117:1888Google Scholar
  111. 111.
    Chen H, Li S (2005) Organometallics 24:872Google Scholar
  112. 112.
    Trost BM, Frederiksen MU, Rudd MT (2005) Angew Chem Int Ed 44:6630Google Scholar
  113. 113.
    Murugesan S, Jiang F, Achard M, Bruneau C, Derien S (2012) Chem Commun 48:6589Google Scholar
  114. 114.
    Gill TP, Mann KR (1982) Organometallics 1:485Google Scholar
  115. 115.
    Trost BM, Older CM (2002) Organometallics 21:2544Google Scholar
  116. 116.
    Kundig EP, Monnier FR (2004) Adv Synth Catal 346:901Google Scholar
  117. 117.
    Donohoe TJ, Basutto JA, Bower JF, Rathi A (2011) Org Lett 13:1036Google Scholar
  118. 118.
    Movassaghi M, Hill MD (2006) J Am Chem Soc 128:4592Google Scholar
  119. 119.
    Kamatani A, Chatani N, Morimoto T, Murai S (2000) J Org Chem 65:9230Google Scholar
  120. 120.
    Trost BM, Machacek MR (2002) Angew Chem Int Ed 41:4693Google Scholar
  121. 121.
    Marsh GP, Parsons PJ, McCarthy C, Corniquet XG (2007) Org Lett 9:2613Google Scholar
  122. 122.
    Ballini R, Petrini M (2009) ARKIVOC ix:195Google Scholar
  123. 123.
    Schmidt B (2004) Eur J Org Chem 9:1865Google Scholar
  124. 124.
    Sutton AE, Seigal BA, Finnegan DF, Snapper ML (2002) J Am Chem Soc 124:13390Google Scholar
  125. 125.
    Furstner A, Ackermann L, Gabor B, Goddard R, Lehmann CW, Mynott R, Stelzer F, Thiel OR (2001) Chem Eur J 7:3236Google Scholar
  126. 126.
    Kinoshita A, Mori M (1994) Synlett 12:1020Google Scholar
  127. 127.
    Mori M (2010) Materials 3:2087Google Scholar
  128. 128.
    Kinoshita A, Sakakibara N, Mori M (1999) Tetrahedron 55:8155Google Scholar
  129. 129.
    Kitamura T, Sato Y, Mori M (2001) Chem Commun 14:1258Google Scholar
  130. 130.
    Kitamura T, Sato Y, Mori M (2002) Adv Synth Catal 344:678Google Scholar
  131. 131.
    Kalbarczyk KP, Diver ST (2009) J Org Chem 74:2193Google Scholar
  132. 132.
    Buffat MGP (2004) Tetrahedron 60:1701Google Scholar
  133. 133.
    Trost BM, Pinkerton AB, Kremzow D (2000) J Am Chem Soc 122:12007Google Scholar
  134. 134.
    Li GY, Chen J, Yu WY, Hong W, Che CM (2003) Org Lett 5:2153Google Scholar
  135. 135.
    Deng QH, Xu HW, Yuen AWH, Xu ZJ, Che CM (2008) Org Lett 10:1529Google Scholar
  136. 136.
    Naota T, Murahashi S (1991) Synlett 9:693Google Scholar
  137. 137.
    Trost BM, Maulide N, Livingston RC (2008) J Am Chem Soc 130:16502Google Scholar
  138. 138.
    Abrunhosa-Thomas I, Roy O, Barra M, Besset T, Chalard P, Troin Y (2007) Synlett 10:1613Google Scholar
  139. 139.
    Watson PS, Jiang B, Scott B (2000) Org Lett 2:3679Google Scholar
  140. 140.
    Trost BM (1991) Science 254:1471Google Scholar
  141. 141.
    Kondo T, Okada T, Mitsudo TA (2002) J Am Chem Soc 124:186Google Scholar
  142. 142.
    Yoshida K, Kawagoe F, Hayashi K, Horiuchi S, Imamoto T, Yanagisawa A (2009) Org Lett 11:515Google Scholar
  143. 143.
    Fu GC, Nguyen ST, Grubbs RH (1993) J Am Chem Soc 115:9856Google Scholar
  144. 144.
    Fu GC, Grubbs RH (1992) J Am Chem Soc 114:7324Google Scholar
  145. 145.
    Rutjes FPJT, Schoemaker HE (1997) Tetrahedron Lett 38:677Google Scholar
  146. 146.
    Taillier C, Hameury T, Bellosta V, Cossy J (2007) Tetrahedron 63:4472Google Scholar
  147. 147.
    Dieters A, Martin SF (2004) Chem Rev 104:2199Google Scholar
  148. 148.
    Chippindale AM, Davies SG, Iwamoto K, Parkin RM, Smethurst CAP, Smith AD, Rodriguez-Solla H (2003) Tetrahedron 59:3253Google Scholar
  149. 149.
    Perlmutter P, Rose M, Vounatsos F (2003) Eur J Org Chem 4:756Google Scholar
  150. 150.
    Davies SG, Iwamoto K, Smethurst CAP, Smith AD, Rodriguez-Solla H (2002) Synlett 7:1146Google Scholar
  151. 151.
    Pachamuthu K, Vankar YD (2001) J Organomet Chem 624:359Google Scholar
  152. 152.
    Davies HML, Venkataramani C (2002) Angew Chem Int Ed 41:2197Google Scholar
  153. 153.
    Fustero S, Jimenez D, Sanchez-Rosello M, del Pozo C (2007) J Am Chem Soc 129:6700Google Scholar
  154. 154.
    Hamid MHSA, Allen CL, Lamb GW, Maxwell AC, Maytum HC, Watson AJA, Williams JMJ (2009) J Am Chem Soc 131:1766Google Scholar
  155. 155.
    Boeda F, Clavier H, Jordaan M, Meyer WH, Nolan SP (2008) J Org Chem 73:259Google Scholar
  156. 156.
    Dondas HA, Clique B, Cetinkaya B, Grigg R, Kilner C, Morris J, Sridharan V (2005) Tetrahedron 61:10652Google Scholar
  157. 157.
    Varela JA, Saa C (2003) Chem Rev 103:3787Google Scholar
  158. 158.
    Nakao Y (2011) Synthesis 20:3209Google Scholar
  159. 159.
    Maier M (2000) Angew Chem Int Ed 39: 2073Google Scholar
  160. 160.
    Huwe CM, Kiehl OC, Blechert S (1996) Synlett 1:65Google Scholar
  161. 161.
    Carda M, Castillo S, Rodriguez S, Uriel S, Marco JA (1999) Synlett 10:1639Google Scholar
  162. 162.
    Rodriguez S, Castillo S, Carda M, Marco JA (2002) Tetrahedron 58:1185Google Scholar
  163. 163.
    Hcck MP, Baylon C, Nolan SP, Mioskowski C (2001) Org Lett 3:1989Google Scholar
  164. 164.
    Kindennan SS, van Maarseveen JH, Schoemaker HE, Hiemstra H, Rutjes FPJT (2001) Org Lett 3:2045Google Scholar
  165. 165.
    Chattetjee AK, Grubbs RH (1999) Org Lett 1:1751Google Scholar
  166. 166.
    Scwab P, Grubbs RH, Ziller IW (1996) J Am Chem Soc 118:100Google Scholar
  167. 167.
    Bates RW, Lu Y (2009) J Org Chem 74:9460Google Scholar
  168. 168.
    Nag S, Batra S (2011) Tetrahedron 67:8959Google Scholar
  169. 169.
    Takahashi K, Nakano H, Fujita R (2005) Tetrahedron Lett 46:8927Google Scholar
  170. 170.
    Honda T, Ushiwata M, Mizutani H (2006) Tetrahedron Lett 47:6251Google Scholar
  171. 171.
    Wybrow RAJ, Edwards AS, Stevenson NG, Adams H, Johnstone C, Harrity JPA (2004) Tetrahedron 60:8869Google Scholar
  172. 172.
    Schurer SC, Blechert S (1999) Tetrahedron Lett 40:1877Google Scholar
  173. 173.
    Diver ST, Giessert AJ (2004) Chem Rev 104:1317Google Scholar
  174. 174.
    Cho J, Lee YM, Kim D, Kim S (2009) J Org Chem 74:3900Google Scholar
  175. 175.
    Nagahara Y, Shinomiya T, Kuroda S, Kaneko N, Nishio R, Ikekita M (2005) Cancer Sci 96:83Google Scholar
  176. 176.
    Katoh M, Matsune R, Nagase H, Honda T (2004) Tetrahedron Lett 45:6221Google Scholar
  177. 177.
    Alegret C, Ginesta X, Riera A (2008) Eur J Org Chem 10:1789Google Scholar
  178. 178.
    Lesma G, Landoni N, Sacchetti A, Silvani A (2010) Tetrahedron 66:4474Google Scholar
  179. 179.
    Singh GS, Desta ZY (2012) Chem Rev 112:6104Google Scholar
  180. 180.
    Zibuck R, Streiber J (1998) Org Synth 9:432Google Scholar
  181. 181.
    Kotha S, Sreenivasachary N (2001) Eur J Org Chem 17:3375Google Scholar
  182. 182.
    Kotha S, Sreenivasachary N (2000) Chem Commun 6:503Google Scholar
  183. 183.
    Mujahidin D, Doye S (2005) Eur J Org Chem 13:2689Google Scholar
  184. 184.
    Uematsu N, Fujii A, Hashiguchi S, Ikariya T, Noyori R (1996) J Am Chem Soc 118:4916Google Scholar
  185. 185.
    Muller TE, Hultzsch KC, Yus M, Foubelo F, Tada M (2008) Chem Rev 108:3795Google Scholar
  186. 186.
    Trost BM, Gutierrez AC (2007) Org Lett 9:1473Google Scholar
  187. 187.
    Gutierrez AC, Trost BM (2007) Org Lett 9:1473Google Scholar
  188. 188.
    Rudd MT, Trost BM (2002) J Am Chem Soc 124:4178Google Scholar
  189. 189.
    Yamamoto Y, Takagishi H, Itoh K (2001) Org Lett 3:2117Google Scholar
  190. 190.
    Yamamoto Y, Okuda S, Itoh K (2001) Chem Commun 12:1102Google Scholar
  191. 191.
    Hong P, Yamazaki H (1977) Tetrahedron Lett 18:1333Google Scholar
  192. 192.
    Hoberg H, Oster BW (1982) Synthesis 4:324Google Scholar
  193. 193.
    Yamamoto Y, Ogawa R, Itoh K (2001) J Am Chem Soc 123:6189Google Scholar
  194. 194.
    Kotha S, Brahmachary E, Lahiri K (2005) Eur J Org Chem 22:4741Google Scholar
  195. 195.
    Yamamoto Y, Kinpara K, Saigoku T, Takagishi H, Okuda S, Nishiyama H, Itoh K (2005) J Am Chem Soc 127:605Google Scholar
  196. 196.
    Varela JA, Castedo L, Saa C (2003) J Org Chem 68:8595Google Scholar
  197. 197.
    Mori M, Kuzuba Y, Kitamura T, Sato Y (2002) Org Lett 4:3855Google Scholar
  198. 198.
    Kitamura T, Kuzuba Y, Sato Y, Wakamatsu H, Fujita R, Mori M (2004) Tetrahedron 60:7375Google Scholar
  199. 199.
    Barrett AGM, Baugh SPD, Braddock DC, Flack K, Gibson VC, Giles MR, Marshall EL, Procopiou PA, White AJP, Williams DJ (1998) J Org Chem 63:7893Google Scholar
  200. 200.
    Duboc R, Henaut C, Savignac M, Genet JP, Bhatnagar N (2001) Tetrahedron Lett 42:2461Google Scholar
  201. 201.
    Tarling CA, Holmes AB, Markwell RE, Pearson ND (1999) J Chem Soc Perkin Trans 1 12:1695Google Scholar
  202. 202.
    Alcaide B, Almendros P (2010) Topics Heterocycl Chem 22:1Google Scholar
  203. 203.
    Desroy N, Robert-Peillard F, Toueg J, Duboc R, Henaut C, Rager MN, Savignac M, Genet JP (2004) Eur J Org Chem 23:4840Google Scholar
  204. 204.
    Desroy N, Robert-Peillard F, Toueg J, Henaut C, Duboc R, Rager MN, Savignac M, Genet JP (2004) Synthesis 16:2665Google Scholar
  205. 205.
    Nath M, Mukhopadhyay R, Bhattacharyya A (2006) Org Lett 8:317Google Scholar
  206. 206.
    Arjona O, Csaky AG, Murcia MC, Plumet J (2000) Tetrahedron Lett 41:9777Google Scholar
  207. 207.
    Arjona O, Csaky AG, Leon V, Medel R, Plumet J (2004) Tetrahedron Lett 45:565Google Scholar
  208. 208.
    Mori M, Wakamatsu H, Sato Y, Fujita R (2006) J Mol Cat A: Chem 254:64Google Scholar
  209. 209.
    Arisawa M, Takezawa E, Nishida A, Mori M, Nakagawa M (1997) Synlett 10:1179Google Scholar
  210. 210.
    Ben-Othman R, Othman M, Ciamala K, Knorr M, Strohmann C, Decroix B (2009) Tetrahedron 65:4846Google Scholar
  211. 211.
    Lesma G, Colombo A, Sacchetti A, Silvani A (2009) J Org Chem 74:590Google Scholar
  212. 212.
    Kim S, Lee T, Lee E, Lee J, Fan GJ, Lee SK, Kim D (2004) J Org Chem 69:3144Google Scholar
  213. 213.
    Yi CS, Yun SY, Guzei IA (2005) J Am Chem Soc 127:5782Google Scholar
  214. 214.
    Fukuda Y, Shindo M, Shishido K (2003) Org Lett 5:749Google Scholar
  215. 215.
    Hoveyda AH, Malcolmson SJ, Meek SJ, Zhugralin AR (2010) Angew Chem Int Ed 49:34Google Scholar
  216. 216.
    Shimizu K, Takimoto M, Mori M (2003) Org Lett 5:2323Google Scholar
  217. 217.
    Benakki H, Colacino E, Andre C, Guenoun F, Martinez J, Lamaty F (2008) Tetrahedron 64:5949Google Scholar
  218. 218.
    Liddel JR (1997) Nat Prod Rep 14:653Google Scholar
  219. 219.
    Ma S, Ni B, Liang Z (2004) J Org Chem 69:6305Google Scholar
  220. 220.
    Ajamian A, Gleason JL (2004) Angew Chem Int Ed 43:3754Google Scholar
  221. 221.
    Shindoh N, Takemoto T, Takasu K (2009) Chem Eur J 15:12168Google Scholar
  222. 222.
    Patil NT, Shinde VS, Gajula B (2012) Org Biomol Chem 10:211Google Scholar
  223. 223.
    Knowles WS (2002) Angew Chem Int Ed 41:1998Google Scholar
  224. 224.
    Noyori R (2002) Angew Chem Int Ed 41:2008Google Scholar
  225. 225.
    Sharpless B (2002) Angew Chem Int Ed 41:2024Google Scholar
  226. 226.
    Grubbs RH (2006) Angew Chem Int Ed 45:3760Google Scholar
  227. 227.
    Angeli M, Bandini M, Garelli A, Piccinelli F, Tommasi S, Umani-Ronchi A (2006) Org Biomol Chem 4:3291Google Scholar
  228. 228.
    Chen Y, Dias HVR, Lovely CJ (2003) Tetrahedron Lett 44:1379Google Scholar
  229. 229.
    Gracias V, Gasiecki AF, Djuric SW (2005) Org Lett 7:3183Google Scholar
  230. 230.
    Arimitsu S, Fernandez B, del Pozo C, Fustero S, Hammond GB (2008) J Org Chem 73:2656Google Scholar
  231. 231.
    Chandrasekhar S, Tiwari B (2009) Tetrahedron: Asymmetry 20:1924Google Scholar
  232. 232.
    Negishi E (2011) Angew Chem Int Ed 50:6738Google Scholar
  233. 233.
    Suzuki A (2011) Angew Chem Int Ed 50:6723Google Scholar
  234. 234.
    Ascic E (2011) Angew Chem Int Ed 50:5188Google Scholar
  235. 235.
    Hong P, Yamazaki H (1977) Synthesis 1:50Google Scholar
  236. 236.
    Hoberg H, Oster BW (1982) J Organomet Chem 234:C35Google Scholar
  237. 237.
    Hoberg H, Oster BW (1983) J Organomet Chem 252:359Google Scholar
  238. 238.
    Earl RA, Vollhardt KPC (1983) J Am Chem Soc 105:6991Google Scholar
  239. 239.
    Yamamoto Y, Kinpara K, Saigoku T, Takagishi H, Okuda S, Nishiyama H, Itoh K (2005) J Am Chem Soc 124:5059Google Scholar
  240. 240.
    Tanaka K, Takahashi Y, Suda T, Hirano M (2008) Synlett 11:1724Google Scholar
  241. 241.
    Tanaka K, Wada A, Nogushi K (2005) Org Lett 7:4737Google Scholar
  242. 242.
    Friedman RK, Oberg KM, Dalton DM, Rovis T (2010) Pure Appl Chem 82:1353Google Scholar
  243. 243.
    Gonzalez-Gomez A, Dominguez G, Perez-Castells J (2005) Tetrahedron Lett 46:7267Google Scholar
  244. 244.
    Huang J, Xiong H, Hsung RP, Rameshkumar C, Mulder JA, Grebe TP (2002) Org Lett 4:2417Google Scholar
  245. 245.
    Perron J, Joseph B, Merour JY (2004) Tetrahedron 60:10099Google Scholar
  246. 246.
    Fukumoto H, Takahashi K, Ishihara J, Hatakeyama S (2006) Angew Chem Int Ed 45:2731Google Scholar

Copyright information

© Springer Science+Business Media, LLC, part of Springer Nature 2019

Authors and Affiliations

  1. 1.Department of ChemistryBanasthali VidyapithBanasthaliIndia

Personalised recommendations