Diastereoselective Synthesis of Heterocycles via Intramolecular Pd-Catalyzed Alkene Aryliodination

Chapter
Part of the Springer Theses book series (Springer Theses)

Abstract

The construction of the carbon–carbon single bond is one of the most important focus in organic synthesis. Due to the ubiquity of this bond in organic molecules, as well as the infinite number of both substitutional and stereochemical combinations, the development of diverse methods which forge this bond has remained a strong focus. As a testament to the value of these methods, the 2010 Nobel Prize in chemistry was awarded to Richard F. Heck, Ei-ichi Negishi and Akira Suzuki for “palladium-catalyzed cross-coupling in organic synthesis”. This important recognition prompted a rapid increase in the world-wide effort to invent new, and elaborate on existing classes of Pd-catalyzed cross-couplings.

References

  1. 1.
    Petrone, D.A., Malik, H.A., Clemenceau, A., Lautens, M.: Org. Lett. 14, 4806 (2012)CrossRefGoogle Scholar
  2. 2.
    Petrone, D.A., Yoon, H., Weinstabl, H., Lautens, M.: Angew. Chem. Int. Ed. 53, 7908 (2014)CrossRefGoogle Scholar
  3. 3.
    Petrone, D.A., Le, C.M., Newman, S.G., Lautens, M.: Pd-catalyzed carboiodination: early developments to recent advancements (Chap. 7). In: Colacot, T. (ed.) New trends in cross-coupling. The Royal Society of Chemistry, Cambridge (2015)Google Scholar
  4. 4.
    Petrone, D.A., Ye, J., Lautens, M.: Chem. Rev. 116, 8003–8004 (2016)CrossRefGoogle Scholar
  5. 5.
    Johansson Seechurn, C.C.C., Kitching, M.O., Colacot, T.J., Snieckus, V.: Angew. Chem. Int. Ed. 51, 5062 (2012)CrossRefGoogle Scholar
  6. 6.
    Negishi, E.: In Negishi E, de Meijere, A. (eds.) Handbook of Organopalladium Chemistry for Organic Synthesis, vol. 1. 1st edn., p. 213. Wiley, New York (2002)Google Scholar
  7. 7.
    Stille, J.K., Lau, K.S.: Acc. Chem. Res. 10, 434 (1977)CrossRefGoogle Scholar
  8. 8.
    Amatore, C., Jutand, A.: J. Organomet. Chem. 576, 254 (1999)CrossRefGoogle Scholar
  9. 9.
    Cadado, A.L., Espinet, P.: Organometallics 17, 954 (1998)CrossRefGoogle Scholar
  10. 10.
    Amii, H., Uneyama, K.: Chem. Rev. 109, 2119 (2009)CrossRefGoogle Scholar
  11. 11.
    Clot, E., Eisenstein, O., Jasim, N., MacGregor, S.A., McGrady, J.E., Perutz, R.N.: Acc. Chem. Res. 44, 333 (2011)CrossRefGoogle Scholar
  12. 12.
    Ohashi, M., Shibata, M., Saijo, H., Kambara, T., Ogoshi, S.: Organometallics 32, 3631 (2013)CrossRefGoogle Scholar
  13. 13.
    de Jong, G.T., Bickelhaupt, F.M.: J. Phys. Chem. A 109, 9685 (2005)CrossRefGoogle Scholar
  14. 14.
    Collman, J.P., Hegedus, L.S., Norton, J.R., Finke, R.G.: Principles and applications of organotransition metal chemistry, 2nd edn, pp. 176–258. University Science Books, Mill Valley (1987)Google Scholar
  15. 15.
    Spessard, G.O., Meissler, G.L.: Organometallic chemistry, pp. 171–175. Prentice Hall, Upper Saddle River, New Jersey (1996)Google Scholar
  16. 16.
    Christmann, U., Vilar, R.: Angew. Chem. Int. E. 44, 366 (2005)CrossRefGoogle Scholar
  17. 17.
    Hartwig, J.F.: Organotransition metal chemistry: from bonding to catalysis, 1st edn, pp. 895–898. University Science Books, Mill Valley (2010)Google Scholar
  18. 18.
    Mateo, C., Fernández-Rivas, C., Echavarren, A.M., Cárdenes, D.J.: J Organometallics 16, 1997 (1997)CrossRefGoogle Scholar
  19. 19.
    Denmark, S.E., Sweise, R.F.: Acc. Chem. Res. 35, 835 (2002)CrossRefGoogle Scholar
  20. 20.
    Miyaura, N., Yamada, K., Sufinome, H., Suzuki, A.: J. Am. Chem. Soc. 107, 972 (1985)CrossRefGoogle Scholar
  21. 21.
    Lennox, A.J.J., Lloyd-Jones, G.C.: Angew. Chem. Int. Ed. 52, 7362 (2013)CrossRefGoogle Scholar
  22. 22.
    Ridgway, B.H., Woerpel, K.A.: J. Org. Chem. 63, 458 (1998)CrossRefGoogle Scholar
  23. 23.
    Matos, K., Soderquist, J.A.: J. Org. Chem. 63, 461 (1998)CrossRefGoogle Scholar
  24. 24.
    Miyaura, N.: Top. Curr. Chem. 219, 11 (2002)CrossRefGoogle Scholar
  25. 25.
    Cárdenes, D.J., Mateo, C., Echavarren, A.M.: Angew. Chem. Int. Ed. 33, 2445 (1996)CrossRefGoogle Scholar
  26. 26.
    Casado, A.L., Espinet, P.: J. Am. Chem. Soc. 120, 8978 (1998)CrossRefGoogle Scholar
  27. 27.
    Icci, A., Angelucci, F., Bassetti, L., Lo Sterzo, C.: J. Am. Chem. Soc. 124, 1060 (2002)CrossRefGoogle Scholar
  28. 28.
    Cotter, W.D., Barbour, L., McNamera, K.L., Hechter, R., Lachicotte, R.J.: J. Am. Chem. Soc. 120, 11016 (1998)CrossRefGoogle Scholar
  29. 29.
    Hartwig, J.F.: Inorg. Chem. 46, 1936 (2007)CrossRefGoogle Scholar
  30. 30.
    Heck, R.F.: J. Am. Chem. Soc. 90, 5518 (1968)CrossRefGoogle Scholar
  31. 31.
    Heck, R.F.: J. Am. Chem. Soc. 90, 5526 (1968)CrossRefGoogle Scholar
  32. 32.
    Heck, R.F.: J. Am. Chem. Soc. 90, 5531 (1968)CrossRefGoogle Scholar
  33. 33.
    Heck, R.F.: J. Am. Chem. Soc. 90, 5535 (1968)CrossRefGoogle Scholar
  34. 34.
    Heck, R.F.: J. Am. Chem. Soc. 90, 5538 (1968)CrossRefGoogle Scholar
  35. 35.
    Heck, R.F.: J. Am. Chem. Soc. 90, 5542 (1968)CrossRefGoogle Scholar
  36. 36.
    Heck, R.F.: J. Am. Chem. Soc. 90, 5546 (1968)CrossRefGoogle Scholar
  37. 37.
    Fujiwara, Yuzo, Moritani, I., Danno, S., Asano, R., Teranishi, S.: J. Am. Chem. Soc. 91, 7166 (1968)CrossRefGoogle Scholar
  38. 38.
    Mizoroki, T., Mori, K., Ozaki, A.: Bull. Chem. Soc. Jpn 44, 581 (1971)CrossRefGoogle Scholar
  39. 39.
    Heck, R.F., Nolley, J.P.: J. Org. Chem. 14, 2320 (1972)CrossRefGoogle Scholar
  40. 40.
    Mizoroki, T., Mori, K., Ozaki, A.: Bull. Chem. Soc. Jpn 46, 1505 (1973)CrossRefGoogle Scholar
  41. 41.
    Dieck, H.A., Heck, R.F.: J. Am. Chem. Soc. 96, 1133 (1974)CrossRefGoogle Scholar
  42. 42.
    Coulson, D.R.: Chem. Commun. 1530 (1968)Google Scholar
  43. 43.
    Dieck, H.A., Heck, R.F.: J. Org. Chem. 40, 1083 (1975)CrossRefGoogle Scholar
  44. 44.
    Kim, J.-I.I., Patel, B.A., Heck, R.F.: J. Org. Chem. 46, 1067 (1981)CrossRefGoogle Scholar
  45. 45.
    Ziegler, C.B., Heck, R.F.: J. Org. Chem. 43, 2941 (1978)CrossRefGoogle Scholar
  46. 46.
    Julia, M., Duteil, M., Grard, C., Kuntz, E.: Bull. Soc. Chim. Fr. 2791 (1973)Google Scholar
  47. 47.
    Spencer, A.: J. Organomet. Chem. 270, 115 (1984)CrossRefGoogle Scholar
  48. 48.
    Davison, J.B., Simon, N.M., Sojka, S.A.: J. Mol. Catal. 22, 349 (1984)CrossRefGoogle Scholar
  49. 49.
    Ben-David, Y., Portney, M., Milstein, D.: J. Am. Chem. Soc. 111, 8742 (1989)CrossRefGoogle Scholar
  50. 50.
    Ben-David, Y., Portney, M., Milstein, D.: J. Chem. Soc. Chem. Commun. 1816 (1989)Google Scholar
  51. 51.
    Ben-David, Y., Portney, M., Gozin, M., Milstein, D.: Organometallics 11, 1995 (1992)CrossRefGoogle Scholar
  52. 52.
    Portney, M., Ben-David, Y., Milstein, D.: Organometallics 12, 4734 (1993)CrossRefGoogle Scholar
  53. 53.
    Herrmann, W.A., Brossner, C., Öfele, K., Reisinger, C.-P., Priermeier, T., Beller, M., Fischer, H.: Angew. Chem. Int. Ed. 34, 1844 (1995)CrossRefGoogle Scholar
  54. 54.
    Herrmann, W.A., Elison, M., Fischer, J., Köcher, C., Artus, G.R.J.: Angew. Chem. Int. Ed. 34, 2371 (1995)CrossRefGoogle Scholar
  55. 55.
    Reetz, M.T., Lohmer, G., Schwickardi, R.: Angew. Chem. Int. Ed. 37, 481 (1998)CrossRefGoogle Scholar
  56. 56.
    Ehrentraut, A., Zapf, A., Beller, M.: Synlett 11, 1589 (2000)Google Scholar
  57. 57.
    Kauffmann, D.E., Nouroozian, M., Henze, H., Synlett, 1091 (1996)Google Scholar
  58. 58.
    Beller, M., Zapf, A., Synlett, 792 (1998)Google Scholar
  59. 59.
    Littke, A.F., Fu, G.C.: J. Org. Chem. 64, 10 (1999)CrossRefGoogle Scholar
  60. 60.
    Littke, A.F., Fu, G.C.: J. Am. Chem. Soc. 123, 6989 (2001)CrossRefGoogle Scholar
  61. 61.
    Shaughnessy, K.H., Kim, P., Hartwig, J.F.: J. Am. Chem. Soc. 126, 1184 (2004)CrossRefGoogle Scholar
  62. 62.
    Heck, R.F.: Org. React. 27, 345 (1982)Google Scholar
  63. 63.
    Davies, G.D., Hallberg, A.: Chem. Rev. 89, 1433 (1989)CrossRefGoogle Scholar
  64. 64.
    Heck, R.F.: In: Trost, B.M., Flemming, I. (eds.), Comprehensive Organic Synthesis, vol. 4. Permagon Press, Oxford (1991)Google Scholar
  65. 65.
    De Meijere, A., Meyer, F.E.: Angew. Chem. Int. Ed. 33, 2739 (1994)CrossRefGoogle Scholar
  66. 66.
    Brase, S., deMeijere, A.: In: Diederich, F., Stang, P.J. (eds.) Metal-Catalyzed Cross-Coupling Reactions. Wiley, New York (1998)Google Scholar
  67. 67.
    Beletskaya, I.P., Cheprakov, A.V.: Chem. Rev. 100, 3009 (2000)CrossRefGoogle Scholar
  68. 68.
    Beletskaya, I.P., Cheprakov, A.V.: In T. Colacot, (ed.) New Trends in Cross-Coupling: Theory and Application, pp. 355–478 . The Royal Society of Chemistry, Cambridge (2015)Google Scholar
  69. 69.
    DeAngelis, A., Colacot, T.J.: In Colacot, T. (ed.) New Trends in Cross-Coupling: Theory and Application, pp. 20–90. The Royal Society of Chemistry, Cambridge (2015)Google Scholar
  70. 70.
    Chartoire, A., Nolan, S.P.: In Colacot, T. (ed.), New Trends in Cross-Coupling: Theory and Application, pp. 139–227. The Royal Society of Chemistry, Cambridge (2015)Google Scholar
  71. 71.
    Negishi, E.-I., Coperet, C., Ma, S., Liou, S.-Y., Liu, F.: Chem. Rev. 96, 365 (1996)CrossRefGoogle Scholar
  72. 72.
    Negishi, E.-i, Copéret, C., Ma, S., Liou, S.-Y., Liu, F.: Chem. Rev. 95, 365 (1996)CrossRefGoogle Scholar
  73. 73.
    Mori, M., Chiba, K., Ban, Y.: Tetrahedron Lett. 18, 1037 (1977)CrossRefGoogle Scholar
  74. 74.
    Cortese, N.A., Ziegler, C.B., Hrnjez, B.J., Heck, R.F.: J. Org. Chem. 43, 2952 (1978)CrossRefGoogle Scholar
  75. 75.
    Odle, R., Belvins, B., Ratcliff, M., Hegedus, L.S.: J. Org. Chem. 45, 2790 (1980)CrossRefGoogle Scholar
  76. 76.
    Narula, C.K., Mak, K.T., Heck, R.F.: J. Org. Chem. 48, 2792 (1983)CrossRefGoogle Scholar
  77. 77.
    Grigg, R., Stevenson, P., Worakun, T.: J. Chem. Soc. Chem. Commun. 1073 (1984)Google Scholar
  78. 78.
    Tour, J.M., Negishi, E.-I.: J. Am. Chem. Soc. 107, 8289 (1985)CrossRefGoogle Scholar
  79. 79.
    Abelman, M.M., Oh, T., Overman, L.E.: J. Org. Chem. 52, 4130 (1987)CrossRefGoogle Scholar
  80. 80.
    Larock, R.C., Song, H., Baker, B.E., Gong, W.H.: Tetrahedron Lett. 29, 2919 (1988)CrossRefGoogle Scholar
  81. 81.
    Negishi, E.-I., Zhang, Y., O’Connor, B.: Tetrahedron Lett. 29, 2915 (1988)CrossRefGoogle Scholar
  82. 82.
    Sato, Y., Sodeoka, M., Shibasaki, M.: Chem. Lett. 19, 1953 (1990)CrossRefGoogle Scholar
  83. 83.
    Nicolaou, K.C., Bulger, P.G., Sarlah, D.: Angew. Chem. Int. Ed. 44, 4442 (2005)CrossRefGoogle Scholar
  84. 84.
    Jeffery, T.: Tetrahedron 52, 10113 (1996)CrossRefGoogle Scholar
  85. 85.
    Danishefsky, S.J., Masters, J.J., Young, W.B., Link, J.T., Synder, L.B., Magee, T.V., Kung, D.K., Isaacs, R.C.A., Bornmann, W.G., Alaimo, C.A., Coburn, C.A., Di Grandi, M.J.: J. Am. Chem. Soc. 118, 2843 (1996)CrossRefGoogle Scholar
  86. 86.
    Kagan, H.B., Diter, P., Gref, A., Guillaneux, D., Masson-Szymcak, A., Rebriére, F., Riant, O., Samuel, O., Taidien, S.: Pure Appl. Chem. 68, 29 (1996)CrossRefGoogle Scholar
  87. 87.
    Shibasaki, M., Boden, C.D.J., Kojima, A.: Tetrahedron 53, 7371 (1997)CrossRefGoogle Scholar
  88. 88.
    Shibasaki, M., Vogl, E.M., Ohshima, T.: Adv. Synth. Catal. 346, 1533 (2004)CrossRefGoogle Scholar
  89. 89.
    Sato, Y., Sodeoka, M., Shibasaki, M.: J. Org. Chem. 54, 4738 (1989)CrossRefGoogle Scholar
  90. 90.
    Carpenter, N.E., Kucera, D.J., Overman, L.E.: J. Org. Chem. 54, 5846 (1989)CrossRefGoogle Scholar
  91. 91.
    Ozawa, F., Kubo, A., Hayashi, T.: J. Am. Chem. Soc. 113, 1417 (1991)CrossRefGoogle Scholar
  92. 92.
    Cabri, W., Candiani, I., DeBernardinis, S., Francalanci, F., Penco, S.: J. Org. Chem. 56, 5796 (1991)CrossRefGoogle Scholar
  93. 93.
    Brown, J.M., Pérez-Torrente, J., Alcock, N.W., Clase, H.J.: Organometallics 14, 207 (1995)CrossRefGoogle Scholar
  94. 94.
    Brown, J.M., Hii, K.K.: Angew. Chem. Int. Ed. 35, 657 (1996)CrossRefGoogle Scholar
  95. 95.
    Hii, K.K., Claridge, T.D.W., Brown, J.M., Smith, A., Deeth, R.J.: Helv. Chim. Acta 84, 3043 (2001)CrossRefGoogle Scholar
  96. 96.
    Ashimori, A., Overman, L.E.: J. Org. Chem. 57, 4571 (1992)CrossRefGoogle Scholar
  97. 97.
    Overman, L.E., Poon, D.J.: Angew. Chem. Int. Ed. 36, 519 (1997)CrossRefGoogle Scholar
  98. 98.
    Thorn, D.L., Hoffman, R.: J. Am. Chem. Soc. 100, 2079 (1978)CrossRefGoogle Scholar
  99. 99.
    Samsel, E.G., Norton, J.R.: J. Am. Chem. Soc. 106, 5505 (1984)CrossRefGoogle Scholar
  100. 100.
    Ashimori, A., Bachand, B., Calter, M.A., Govek, S.P., Overman, L.E., Poon, D.J.: J. Am. Chem. Soc. 120, 6488 (1998)CrossRefGoogle Scholar
  101. 101.
    Lapierre, A.J.B., Geib, S.J., Curran, D.P.: J. Am. Chem. Soc. 129, 494 (2007)CrossRefGoogle Scholar
  102. 102.
    Tsuji, J.: Palladium Reagents and Catalysts—New Perspectives for the 21st Century, 2nd edn, pp. 1–26. Wiley, West Sussex (2004)CrossRefGoogle Scholar
  103. 103.
    Vigalok, A.: Chem. Eur. J. 14, 5102 (2008)CrossRefGoogle Scholar
  104. 104.
    Casado, A.L., Espinet, P.: J. Am. Chem. Soc. 120, 9878 (1998)CrossRefGoogle Scholar
  105. 105.
    Xue, L., Lin, Z.: Chem. Soc. Rev. 39, 1692 (2010)CrossRefGoogle Scholar
  106. 106.
    Ettorre, R.: Inorg. Nuc. Chem. Lett. 5, 45 (1968)CrossRefGoogle Scholar
  107. 107.
    Fahey, D.R.: J. Chem. Soc. Chem. Commun. 417 (1970)Google Scholar
  108. 108.
    Fahey, D.R.: J. Organomet. Chem. 27, 283 (1971)CrossRefGoogle Scholar
  109. 109.
    Roy, A.H., Hartwig, J.F.: J. Am. Chem. Soc. 123, 1232 (2001)CrossRefGoogle Scholar
  110. 110.
    Roy, A.H., Hartwig, J.F.: Organometallics 23, 1533 (2004)CrossRefGoogle Scholar
  111. 111.
    Littke, A.F., Dai, C., Fu, G.C.: J. Am. Chem. Soc. 122, 4020 (2000)CrossRefGoogle Scholar
  112. 112.
    Alcazar-Roman, L.M., Hartwig, J.F.: J. Am. Chem. Soc. 123, 12905 (2000)CrossRefGoogle Scholar
  113. 113.
    Stambuli, J.P., Bühl, M., Hartwig, J.F.: J. Am. Chem. Soc. 124, 9346 (2002)CrossRefGoogle Scholar
  114. 114.
    Roy, A.H., Hartwig, J.F.: J. Am. Chem. Soc. 125, 13944 (2003)CrossRefGoogle Scholar
  115. 115.
    Grushin, V.V., Alper, H.: Chem. Rev. 94, 1047 (1994)CrossRefGoogle Scholar
  116. 116.
    Lam, K.C., Marder, T.B., Lin, Z.: Organometallics 26, 758 (2007)CrossRefGoogle Scholar
  117. 117.
    Yahav-Levi, A., Goldberg, I., Vigalok, A.: J. Am. Chem. Soc. 128, 8710 (2006)CrossRefGoogle Scholar
  118. 118.
    Ruddick, J.D., Shaw, B.L.: J. Chem. Soc. (A) 2969 (1969)Google Scholar
  119. 119.
    Goldberg, K.I., Yan, J.Y., Winter, E.L.: J. Am. Chem. Soc. 116, 1573 (1994)CrossRefGoogle Scholar
  120. 120.
    Goldberg, K.I., Yan, J.Y., Breitung, E.M.: J. Am. Chem. Soc. 117, 6889 (1995)CrossRefGoogle Scholar
  121. 121.
    Maitlis, P.M., Haynes, A., Sunley, G.J., Howard, M.J.: J. Chem. Soc. Dalton Trans. 2187 (1996)Google Scholar
  122. 122.
    Kampmeier, J.A., Rodehorst, R.M., Phillip, J.B.: J. Am. Chem. Soc. 103, 1847 (1981)CrossRefGoogle Scholar
  123. 123.
    Gonsalvi, L., Gaunt, J.A., Adams, H., Castro, A., Sunley, G.J., Haynes, A.: Organometallics 22, 1047 (2003)CrossRefGoogle Scholar
  124. 124.
    Frech, C.M., Milstein, D.: J. Am. Chem. Soc. 128, 12434 (2006)CrossRefGoogle Scholar
  125. 125.
    Newman, S.G., Lautens, M.: J. Am. Chem. Soc. 132, 11416 (2010)CrossRefGoogle Scholar
  126. 126.
    Newman, S.G., Lautens, M.: J. Am. Chem. Soc. 133, 1778 (2011)CrossRefGoogle Scholar
  127. 127.
    Shelby, Q., Kataoka, N., Mann, G., Hartwig, J.F.: J. Am. Chem. Soc. 122, 10718 (2000)CrossRefGoogle Scholar
  128. 128.
    Tollman, C.A.: Chem. Rev. 77, 313 (1977)CrossRefGoogle Scholar
  129. 129.
    Lan, Y., Liu, P., Newman, S.G., Lautens, M., Houk, K.N.: Chem. Sci. 3, 1987 (2012)CrossRefGoogle Scholar
  130. 130.
    Liu, H., Li, C., Qiu, D., Tong, X.: J. Am. Chem. Soc. 133, 6187 (2011)CrossRefGoogle Scholar
  131. 131.
    Newman, S.G., Howell, J.K., Nicolaus, N., Lautens, M.: J. Am. Chem. Soc. 133, 14916 (2011)CrossRefGoogle Scholar
  132. 132.
    Klapars, A., Buchwald, S.L.: J. Am. Chem. Soc. 124, 14844 (2002)CrossRefGoogle Scholar
  133. 133.
    Jia, X., Petrone, D.A., Lautens, M.: Angew. Chem. Int. Ed. 51, 9870 (2012)CrossRefGoogle Scholar
  134. 134.
    Ellis, G.P., Lockhart, I.M.: In Ellis, G.P. (eds.) The Chemistry of Heterocyclic Compounds, Chromenes, Chromanones, and Chromones. Wiley-VCH, New York (1977)Google Scholar
  135. 135.
    Kamigauchu, M., Noda, Y., Nishijo, J., Iwasaki, K., Tobetto, K., In, Y., Tomoo, K., Ishita, T.: Bioorg, Med. Chem. Let. 13, 1867 (2005)Google Scholar
  136. 136.
    Kim, D.K.: Arch. Pharmacal Res. 25, 817 (2002)CrossRefGoogle Scholar
  137. 137.
    Ma, W.G., Fukushi, Y., Tahara, S.: Fitoterapia 70, 258 (1999)CrossRefGoogle Scholar
  138. 138.
    Ninomiya, I., Yamamoto, O., Naito, T.: J. Chem. Soc. Chem. Commun. 437 (1976)Google Scholar
  139. 139.
    Cushman, M., Abbaspour, A., Gupta, Y.P.: J. Am. Chem. Soc. 105, 2873 (1983)CrossRefGoogle Scholar
  140. 140.
    Cushman, M., Abbaspour, A., Gupta, Y.P.: J. Am. Chem. Soc. 112, 5898 (1990)CrossRefGoogle Scholar
  141. 141.
    Hanaoka, M., Yoshida, S., Mukai, C.: Tetrahedron Lett. 29, 6621 (1988)CrossRefGoogle Scholar
  142. 142.
    Cushman, M., Chen, J.-K.: J. Org. Chem. 52, 1517 (1987)CrossRefGoogle Scholar
  143. 143.
    Tani, C., Takao, N.: Yakugaku Zasshi 82, 755 (1962)CrossRefGoogle Scholar
  144. 144.
    Nielsen, L., Lindsay, K.B., Faber, J., Nielsen, N.C., Skrydstrup, T.: J. Org. Chem. 72, 10035 (2007)CrossRefGoogle Scholar
  145. 145.
    Low, D.W., Pattison, G., Wieczsysty, M.D., Churchill, G.H., Lam, H.W.: Org. Lett. 14, 2548 (2012)CrossRefGoogle Scholar
  146. 146.
    Weinstabl, H., Suhartono, M., Qureshi, Z., Lautens, M.: Angew. Chem. Int. Ed. 52, 5305 (2012)CrossRefGoogle Scholar
  147. 147.
    Blackmond, D.G.: Angew. Chem. Int. Ed. 44, 4302 (2005)CrossRefGoogle Scholar
  148. 148.
    Maresca, L., Natile, G.: Comments Inorg. Chem. 14, 349 (1993)CrossRefGoogle Scholar
  149. 149.
    Albano, V.G., Natile, G., Panunzi, A.: Cood. Chem. Rev. 133, 67 (1994)CrossRefGoogle Scholar
  150. 150.
    Hatano, M., Terada, M., Mikami, K.: Angew. Chem. Int. Ed. 40, 249 (2001)CrossRefGoogle Scholar
  151. 151.
    Greeves, N.: Reduction of C=O to CHOH by metal hydrides. In: Trost, T., Flemming, I. (eds.) Comprehensive Organic Synthesis, vol. 7. Permagon Press, Oxford (1991)Google Scholar
  152. 152.
    Gabbutt, C.D., Heron, B.M., Instone, A.C.: Tetrahedron 62, 737 (2006)CrossRefGoogle Scholar
  153. 153.
    Subramanian, V., Batchu, B.R., Barange, D., Pal, M.: J. Org. Chem. 70, 4778 (2005)CrossRefGoogle Scholar
  154. 154.
    Miura, K., Wang, D., Hosomi, A.: J. Am. Chem. Soc. 127, 9366 (2005)CrossRefGoogle Scholar
  155. 155.
    Mizuno, A., Kusama, H., Iwasawa, N.: Chem. Eur. J. 16, 8248 (2010)CrossRefGoogle Scholar
  156. 156.
    Hurada, T., Kurokawa, H., Kagamikhara, Y., Tanaka, S., Inoue, A., Oku, A.: J. Org. Chem. 57, 1412 (1992)CrossRefGoogle Scholar
  157. 157.
    Zhao, J.-F., Loh, T.-P.: Angew. Chem. Int. Ed. 48, 7232 (2009)CrossRefGoogle Scholar
  158. 158.
    Shchepin, R., Xu, C., Dussault, P.: Org. Lett. 12, 4772 (2010)CrossRefGoogle Scholar
  159. 159.
    Nakajima, M., Kotani, S., Ishizaka, T., Hashimoto, S.: Terahedron Lett. 46, 157 (2005)CrossRefGoogle Scholar
  160. 160.
    Hon, Y.-S., Hsu, T.-R., Chen, C.-Y., Lin, Y.-H., Chnag, F.-J., Hseish, C.-H., Szu, P.: Tetrahedron 59, 1509 (2003)CrossRefGoogle Scholar
  161. 161.
    Zheng, J.-S., Chang, H.-N., Liu, L., Wang, F.-L.: J. Am. Chem. Soc. 133, 11080 (2011)CrossRefGoogle Scholar
  162. 162.
    Joly, G.D., Jacobsen, E.N.: Org. Lett. 4, 1795 (2002)CrossRefGoogle Scholar
  163. 163.
    Druais, V., Hall, M.J., Corsi, C., Wandeborn, S.V., Meyer, C., Cossy, J.: Tetrahedron 66, 6358 (2010)CrossRefGoogle Scholar
  164. 164.
    He, H., Zaturska, D., Kim, J., Aguirre, J., Llauger, L., She, Y., Wu, N., Immormino, R.M., Gewirth, D.T., Chiosis, H.: J. Med. Chem. 49, 381 (2006)CrossRefGoogle Scholar
  165. 165.
    Weinstabl, H., Suhartono, M., Qureshi, Z., Lautens, M.: Angew. Chem. Int. Ed. 52, 5305 (2013)CrossRefGoogle Scholar
  166. 166.
    Mattson, R.J., Sloan, C.P., Lockhart, C.C., Catt, J.D., Gao, Q., Huang, S.: J. Org. Chem. 64, 8004 (1999)CrossRefGoogle Scholar
  167. 167.
    Lv, P., Huang, K., Xie, L., Xu, X.: Org. Biomol. Chem. 9, 3133 (2011)CrossRefGoogle Scholar
  168. 168.
    Faber, J., Lindsay, K.B., Nielson, L., Nielson, N.C.: Skrydstrup, Troels. J. Org. Chem. 72, 10035 (2007)CrossRefGoogle Scholar
  169. 169.
    Kosciolowicz, A., Rozwadowska, M.D.: Tetrahedron Asymmetry 17, 1444 (2007)CrossRefGoogle Scholar
  170. 170.
    Amin, S.R., Bean, C.J., Bettigeri, S.V., Forbes, D.C., Law, A.M., Stockman, R.A.: Synth. Commun. 39, 2405 (2009)CrossRefGoogle Scholar
  171. 171.
    Esumi, T., Fukino, M., Hatakeyama, S., Ishihara, J., Okamoto, N., Shibahara, S., Takahashi, K., Tashiro, Y.: Synthesis 17, 2935 (2009)Google Scholar
  172. 172.
    Bjerglund, K., Friis, S., Hernandez, D., Lindsay, K.B., Mittag, T., Mose, R., Nielsen, L., Skrydstrup, T.: J. Org. Chem. 75, 3283 (2010)CrossRefGoogle Scholar
  173. 173.
    Ackerman, L., Lygin, L.V., Hofmann, N.: Angew. Chem. Int. Ed. 50, 6379 (2011)CrossRefGoogle Scholar
  174. 174.
    Grigg, R., Sansano, J.M., Santhakumar, V., Sridharan, V., Thangavelanthum, R., Thornton-Pett, M., Wilson, D.: Tetrahedron Lett. 53, 11803 (1997)CrossRefGoogle Scholar

Copyright information

© Springer International Publishing AG, part of Springer Nature 2018

Authors and Affiliations

  1. 1.Laboratory for Organic ChemistryETH ZürichZürichSwitzerland

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