Selective carbon-carbon bond cleavage for the stereoselective synthesis of acyclic systems

Angewandte Chemie - International Edition

Volumn 54, Issue 2, 2015, Pages 414-429

  Marek, Ilan ^a   Masarwa, Ahmad ^a   Delaye, Pierre Olivier ^a   Leibeling, Markus ^a  

^a TECHNION ISRAEL INSTITUTE OF TECHNOLOGY   (Israel)

Author keywords

C C activation; Carbometalation; Ring opening; Stereocenters; Strained molecules

Indexed keywords

COVALENT BONDS; FUNCTIONAL GROUPS; PLANNING; STEREOCHEMISTRY; STEREOSELECTIVITY;

C-C ACTIVATIONS; CARBOMETALATION; RING OPENING; STEREOCENTERS; STRAINED MOLECULES;

CARBON;

EID: 84923022319     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201405067     Document Type: Review

References (251)

1. E. M. Carreira, L. Kvaerno, Classics in Stereoselective Synthesis, Wiley-VCH, Weinheim, 2009.
2. a) P. A. Wender, B. L. Miller, Nature 2009, 460, 197;
3. b) N. Z. Burns, P. S. Baran, R.W. Hoffmann, Angew. Chem. 2009, 121, 2896;
4. Angew. Chem. Int. Ed. 2009, 48, 2854;
5. c) P. S. Baran, T. J. Maimone, J. M. Richter, Nature 2007, 446, 404;
6. d) B. M. Trost, Science 1991, 254, 1471.
7. a) K. Ruhland, Eur. J. Org. Chem. 2012, 2683;
8. b) C. Aïssa, Synthesis 2011, 3389;
9. c) M. Murakami, T. Matsuda, Chem. Commun. 2011, 47, 1100;
10. d) H. Yorimitsu, K. Oshima, Bull. Chem. Soc. Jpn. 2009, 82, 778;
11. e) Y. J. Park, J.-W. Park, C.-H. Junn, Acc. Chem. Res. 2008, 41, 222;
12. f) M. Murakami, M. Makino, S. Ashida, T. Matsuda, Bull. Chem. Soc. Jpn. 2006, 79, 1315;
13. g) J. A. Tunge, E. C. Burger, Eur. J. Org. Chem. 2005, 1715;
14. h) C.-H. Jun, Chem. Soc. Rev. 2004, 33, 610;
15. i) C. Perthuisot, B. L. Edelbach, D. L. Zubris, N. Simhai, C. N. Iverson, C. Müller, T. Satoh, W. D. Jones, J. Mol. Catal. A 2002, 189, 157;
16. j) M. Murakami, Y. Ito, Top. Organomet. Chem. 1999, 3, 97;
17. k) J. L. Beauchamps, Chem. Rev. 1990, 90, 629.
18. a) L. Ackermann, Acc. Chem. Res. 2013, 46, 281;
19. b) K. M. Engle, T.-S. Mei, M. Wasa, J.-Q. Yu, Acc. Chem. Res. 2012, 45, 788;
20. c) L. Ackermann, Modern Arylation Methods, Wiley-VCH, Weinheim, 2009;
21. d) R.G. Bergman, Science 1984, 223, 902.
22. B. Rybtchinski, D. Milstein, Angew. Chem. 1999, 111, 918;
23. Angew. Chem. Int. Ed. 1999, 38, 870.
24. M. Gozin, A. Weisman, Y. Ben-David, D. Milstein, Nature 1993, 364, 699.
25. M. Gozin, M. Aizenberg, S.-Y. Liou, A. Weisman, Y. Ben-David, D. Milstein, Nature 1994, 370, 42.
26. A. Maercker, J. D. Roberts, J. Am. Chem. Soc. 1966, 88, 1742.
27. a) C. A. Carson, M. A. Kerr, Chem. Soc. Rev. 2009, 38, 3051;
28. b) M. Rubin, M. Rubina, V. Gevorgyan, Chem. Rev. 2007, 107, 3117;
29. c) M. Yu, B. L. Pagenkopf, Tetrahedron 2005, 61, 321;
30. d) M. Rubina, V. Gevorgyan, Tetrahedron 2004, 60, 3129;
31. e) O. G. Kulinkovich, Chem. Rev. 2003, 103, 2597.
32. a) G. Audran, H. Pelissier, Adv. Synth. Catal. 2010, 352, 575;
33. b) M. Rubin, M. Rubina, V. Gevorgyan, Chem. Rev. 2007, 107, 3117;
34. c) A. Brandi, S. Cicchi, F. M. Cordero, A. Goti, Chem. Rev. 2003, 103, 1213;
35. d) I. Nakamura, Y. Yamamoto, Adv. Synth. Catal. 2002, 344, 111;
36. e) A. de Meijere, S. I. Kozhushkov, A. F. Khlebnikov, Top. Curr. Chem. 2000, 207, 89;
37. f) A. Goti, F. M. Cordero, A. Brandi, Top. Curr. Chem. 1996, 178, 1;
38. g) M. Lautens, W. Klute, W. Tam, Chem. Rev. 1996, 96, 49;
39. h) P. Binger, U. Schuchardt, Chem. Ber. 1981, 114, 3313.
40. I. Marek, S. Simaan, A. Masarwa, Angew. Chem. 2007, 119, 7508;
41. Angew. Chem. Int. Ed. 2007, 46, 7364.
42. a) T. F. Schneider, J. Kaschel, D. B. Wertz, Angew. Chem. 2014, 126, 5608;
43. Angew. Chem. Int. Ed. 2014, 53, 5504;
44. b) H.-U. Reissig, R. Zimmer, Chem. Rev. 2003, 103, 1151;
45. M. A. Drahl, M. Manpadi, L. J. Williams, Angew. Chem. 2013, 125, 11430;
46. Angew. Chem. Int. Ed. 2013, 52, 11222.
47. M. Lautens, C. Meyer, A. Lorenz, J. Am. Chem. Soc. 1996, 118, 10676.
48. S. Simaan, A. F. G. Goldberg, S. Rosset, I. Marek, Chem. Eur. J. 2010, 16, 774.
49. A. G. Bessmertnykh, K. A. Blinov, Y. K. Grishin, N. A. Donskaya, E. V. Tveritinova, N. M. Yur'eva, I. P. Beletskaya, J. Org. Chem. 1997, 62, 6069.
50. a) S. Simaan, I. Marek, Chem. Commun. 2009, 292;
51. b) A. Masarwa, A. Stanger, I. Marek, Angew. Chem. 2007, 119, 8185;
52. Angew. Chem. Int. Ed. 2007, 46, 8039;
53. c) S. Simaan, A. Masarwa, P. Bertus, I. Marek, Angew. Chem. 2006, 118, 4067;
54. Angew. Chem. Int. Ed. 2006, 45, 3963;
55. d) S. Simaan, I. Marek, Org. Lett. 2007, 9, 2569.
56. a) A. Y. Hong, B. M. Stoltz, Eur. J. Org. Chem. 2013, 2745;
57. b) J. P. Das, I. Marek, Chem. Commun. 2011, 47, 459;
58. c) C. Hawner, A. Alexakis, Chem. Commun. 2010, 46, 7295;
59. d) M. Bella, T. Casperi, Synthesis 2009, 1583;
60. e) P. G. Cozzi, R. Hilgraf, N. Zimmermann, Eur. J. Org. Chem. 2007, 5969;
61. f) I. Marek, G. Sklute, Chem. Commun. 2007, 43, 1683;
62. g) B. M. Trost, C. Jiang, Synthesis 2006, 369;
63. h) J. Christoffers, A. Baro, Adv. Synth. Catal. 2005, 347, 1473;
64. i) I. Denissova, L. Barriault, Tetrahedron 2003, 59, 10105;
65. j) J. Christoffers, A. Mann, Angew. Chem. 2001, 113, 4725;
66. Angew. Chem. Int. Ed. 2001, 40, 4591;
67. k) E. J. Corey, A. Guzman-Perez, Angew. Chem. 1998, 110, 2092;
68. Angew. Chem. Int. Ed. 1998, 37, 388;
69. l) I. Marek, Y. Minko, M. Pasco, T. Mejuch, N. Gilboa, H. Chechik, J. D. Das, J. Am. Chem. Soc. 2014, 136, 2682.
70. S. Simaan, A. Masarwa, E. Zohar, A. Stanger, P. Bertus, I. Marek, Chem. Eur. J. 2009, 15, 8449.
71. The E and Z isomers of ACPs 10 have opposite absolute configurations. The E/Z ratio of (E)-10 is 93:7, and the absolute configuration of (E)-10 is S, whereas (Z)-10 is R-configured. Each geometric isomer was formed with an enantiomeric ratio of > 99:1. Accordingly, in the rhodium-catalyzed hydrosilylation reaction of enantiomerically pure 10 [(E,S)-10/(Z,R)-10 = 93:7], E and Z homoallylsilanes 14 were formed with the same E/Z ratio as that of the starting material [(E,R)-14/(Z, S)-14 = 93:7]. After chromatographic separation of the two isomers, they were each subjected to hydrogenation of the double bond, followed by oxidation. The corresponding saturated alcohols containing a quaternary center were obtained in quantitative yield with an enantiomeric ratio similar to that of the starting material (Scheme 7).
72. M. Suginome, T. Matsuda, Y. Ito, J. Am. Chem. Soc. 2000, 122, 11015.
73. M. Oestreich, E. Hartmann, M. Mewald, Chem. Rev. 2013, 113, 402.
74. T. Ohmura, H. Taniguchi, Y. Kondo, M. Suginome, J. Am. Chem. Soc. 2007, 129, 3518.
75. a) M. Pasco, N. Gilboa, T. Mejuch, I. Marek, Organometallics 2013, 32, 942;
76. b) I. Marek, Tetrahedron 2002, 58, 9463;
77. c) D. S. Matteson, R.W. H. Mah, J. Am. Chem. Soc. 1963, 85, 2599.
78. a) T. Yamamoto, Y. Akai, Y. Nagata, M. Suginome, Angew. Chem. 2011, 123, 9006;
79. Angew. Chem. Int. Ed. 2011, 50, 8844;
80. b) T. Yamamoto, T. Yamada, Y. Nagata, M. Suginome, J. Am. Chem. Soc. 2010, 132, 7899;
81. c) T. Yamamoto, M. Suginome, Angew. Chem. 2009, 121, 547;
82. Angew. Chem. Int. Ed. 2009, 48, 539.
83. Y. Akai, T. Yamamoto, Y. Nagata, T. Ohmura, M. Suginome, J. Am. Chem. Soc. 2012, 134, 11092.
84. T. Ohmura, H. Taniguchi, M. Suginome, Org. Lett. 2009, 11, 2880.
85. H. Taniguchi, T. Ohmira, M. Suginome, J. Am. Chem. Soc. 2009, 131, 11298.
86. K. Ogata, D. Shimada, S. Furuya, S.-I. Fukuzawa, Org. Lett. 2013, 15, 1182.
87. S. Simaan, I. Marek, J. Am. Chem. Soc. 2010, 132, 4066.
88. a) E. Negishi, T. Takahashi, Bull. Chem. Soc. Jpn. 1998, 71, 755;
89. b) E. Negishi, T. Takahashi, Acc. Chem. Res. 1994, 27, 124.
90. A. Masarwa, D. Didier, T. Zabrodski, M. Schinkel, L. Ackermann, I. Marek, Nature 2014, 505, 199.
91. a) N. Chinkov, A. Levin, I. Marek, Angew. Chem. 2006, 118, 479;
92. Angew. Chem. Int. Ed. 2006, 45, 465;
93. b) N. Chinkov, A. Levin, I. Marek, Synlett 2006, 501;
94. c) N. Chinkov, S. Majumdar, I. Marek, J. Am. Chem. Soc. 2003, 125, 13258.
95. a) S. Harada, H. Kiyono, R. Nishio, T. Taguchi, Y. Hanzawa, J. Org. Chem. 1997, 62, 3994;
96. b) P.W. Dimmock, R. Whitby, J. Chem. Soc. Chem. Commun. 1994, 2323.
97. a) L. T. Kliman, S. N. Mlynarski, S. N. Ferris, J. P. Morken, Angew. Chem. 2012, 124, 536;
98. Angew. Chem. Int. Ed. 2012, 51, 521;
99. b) I. Marek, Tetrahedron 2002, 58, 9463;
100. c) D. Brasseur, I. Marek, J.-F. Normant, Tetrahedron 1996, 52, 7235;
101. d) I. Marek, J.-F. Normant, Chem. Rev. 1996, 96, 3241.
102. a) F. Shahera, I. Zouev, I. Marek, Tetrahedron 2004, 60, 1329;
103. b) N. Chinkov, H. Chechik, S. Majumdar, I. Marek, Synthesis 2002, 2473;
104. c) S. Farhat, I. Marek, Angew. Chem. 2002, 114, 1468;
105. Angew. Chem. Int. Ed. 2002, 41, 1410;
106. d) A. Liard, H. Chechik, S. Farhat, N. Molender-Vais, C. Averbuj, I. Marek, J. Organomet. Chem. 2001, 624, 26;
107. e) A. Liard, I. Marek, J. Org. Chem. 2000, 65, 7218.
108. a) M. A. Bowring, R. G. Bergman, T. D. Tilley, J. Am. Chem. Soc. 2013, 135, 13121;
109. b) S. Kundu, J. Choi, D. Y. Wang, Y. Choliy, T. J. Emge, K. Krogh-Jespersen, A. S. Goldman, J. Am. Chem. Soc. 2013, 135, 5127;
110. c) C. Aïssa, D, Crepin, D. J. Tetlow, K. Y. T. Ho, Org. Lett. 2013, 15, 1322;
111. d) N. Ishida, Y. Shimamoto, T. Yano, M. Murakami, J. Am. Chem. Soc. 2013, 135, 19103;
112. e) C. Mukai, Y. Ohta, Y. Oura, Y. Kawaguchi, F. Inagaki, J. Am. Chem. Soc. 2012, 134, 19580;
113. f) D. Crepin, C. Tugny, J. H. Murray, C. Aïssa, Chem. Commun. 2011, 47, 10957;
114. g) J. Choi, D. Y. Wang, S. Kundu, Y. Choliy, T. J. Emge, K. Krogh-Jespersen, A. S. Goldman, Science 2011, 332, 1545;
115. h) D. Crepin, J. Dawick, C. Aïssa, Angew. Chem. 2010, 122, 630;
116. Angew. Chem. Int. Ed. 2010, 49, 620;
117. i) T. Seiser, G. Cathomen, N. Cramer, Synlett 2010, 1699;
118. j) C. Aïssa, A. Fürstner, J. Am. Chem. Soc. 2007, 129, 14836;
119. k) M. Shi, L.-P. Liu, J. Tang, J. Am. Chem. Soc. 2006, 128, 7430;
120. l) C.-H. Jun, C.W. Moon, D.-Y. Lee, Chem. Eur. J. 2002, 8, 2422;
121. m) A. D. Aloise, M. E. Layton, M. D. Shair, J. Am. Chem. Soc. 2000, 122, 12610;
122. n) J. O. Hoberg, P.W. Jennings, J. Am. Chem. Soc. 1990, 112, 5347.
123. A. de Meijere, Chem. Rev. 2003, 103, 931
124. I. Ryu, K, Matsumoto, M. Ando, S. Murai, N. Sonoda, Tetrahedron Lett. 1980, 21, 4283.
125. B. Giese, H. Horler, Tetrahedron Lett. 1983, 24, 3221.
126. O. G. Kulinkovich, Chem. Rev. 2003, 103, 2597.
127. a) E. M. Bassan, C. A. Baxter, G. L. Beutner, K. M. Emerson, F. J. Fleitz, S. Johnson, S. Keen, M. M. Kim, J. T. Kuethe, W. R. Leonard, P. R. Mullens, D. J. Muzzio, C. Roberge, N. Yasuda, Org. Process Res. Dev. 2012, 16, 87;
128. b) T. Imai, H. Mineta, S. Nishida, J. Org. Chem. 1990, 55, 4986.
129. D. B. Collum, F. Mohamadi, J. S. Hallock, J. Am. Chem. Soc. 1983, 105, 6882.
130. A. H. Hoveyda, D. A. Evans, G. C. Fu, Chem. Rev. 1993, 93, 1307.
131. A. B. Charette, A. Beauchemin, Org. React. 2004, 58, 1.
132. D. B. Collum, W. C. Still, F. Mohamadi, J. Am. Chem. Soc. 1986, 108, 2094.
133. P. Kočovský, J. Šrogl, M. Pour, A. Gogoll, J. Am. Chem. Soc. 1994, 116, 186.
134. a) A. G. Barrett, W. Tam, J. Org. Chem. 1997, 62, 4653;
135. b) A. G. M. Barrett, W. Tam, J. Org. Chem. 1997, 62, 7673.
136. a) M. Defosseux, N. Blanchard, C. Meyer, J. Cossy, Tetrahedron 2005, 61, 7632;
137. b) M. Defosseux, N. Blanchard, C. Meyer, J. Cossy, J. Org. Chem. 2004, 69, 4626;
138. c) J. Cossy, N. Blanchard, C. Meyer, Org. Lett. 2001, 3, 2567;
139. d) J. Cossy, N. Blanchard, C. Meyer, Eur. J. Org. Chem. 2001, 2841;
140. e) J. Cossy, N. Blanchard, C. Hamel, C. Meyer, J. Org. Chem. 1999, 64, 2608;
141. f) J. Cossy, N. Blanchard, C. Meyer, Synthesis 1999, 1063;
142. g) J. Cossy, N. Blanchard, C. Meyer, Tetrahedron Lett. 1999, 40, 8361.
143. C. Meyer, N. Blanchard, M. Defosseux, J. Cossy, Acc. Chem. Res. 2003, 36, 766.
144. E. Nakamura, K. Sekiya, I. Kuwajima, Tetrahedron Lett. 1987, 28, 337.
145. a) S. Aoki, T. Fujimura, E. Nakamura, I. Kuwajima, J. Am. Chem. Soc. 1988, 110, 3296;
146. b) D. Rosa, A. Orellana, Org. Lett. 2011, 13, 110;
147. c) D. Rosa, O. Arellana, Chem. Commun. 2012, 48, 1922.
148. E. Nakamura, H. Oshino, I. Kuwajima, J. Am. Chem. Soc. 1986, 108, 3745.
149. K. Nomura, T. Hirayama, S. Matsubara, Chem. Asian J. 2009, 4, 1298.
150. K. Nomura, S. Matsubara, Chem. Asian J. 2010, 5, 147.
151. a) K. Cheng, P. J. Caroll, P. J. Walsh, Org. Lett. 2011, 13, 2346;
152. H. Y. Kim, P. J. Walsh, Acc. Chem. Res. 2012, 45, 1533.
153. D. T. Ziegler, A. M. Steffens, T.W. Funk, Tetrahedron Lett. 2010, 51, 6726.
154. a) P. P. Das, K. Belmore, J. K. Cha, Angew. Chem. 2012, 124, 9655;
155. Angew. Chem. Int. Ed. 2012, 51, 9517;
156. b) P. P. Das, B. B. Parida, J. K. Cha, ARKIVOC 2012, 74.
157. a) D. Rosa, A. Orellana, Chem. Commun. 2013, 49, 5420;
158. b) K. Cheng, P. J. Walsh, Org. Lett. 2013, 15, 2298.
159. B. B. Parida, P. P. Das, M. Niocel, J. K. Cha, Org. Lett. 2013, 15, 1780.
160. a) P. Tang, Y. Qin, Synthesis 2012, 44, 2969;
161. b) M. Yu, B. L. Pagenkopf, Tetrahedron 2005, 61, 321;
162. c) H. N. C. Wong, M.-Y. Hon, C.-W. Tse, Y.-C. Yip, J. Tanko, T. Hudlicky, Chem. Rev. 1989, 89, 165;
163. d) S. Danishefsky, Acc. Chem. Res. 1979, 12, 66;
164. e) The Chemistry of the Cyclopropyl Group, Patai Series (Ed.: Z. Rappoport), Wiley-Interscience, New York, 1995.
165. a) S. M. Wales, M. M. Walker, J. S. Johnson, Org. Lett. 2013, 15, 2558
166. b) Y.-Y. Zhou, L.-J. Wang, J. Li, X.-L. Sun, Y. Tang, J. Am. Chem. Soc. 2012, 134, 9066;
167. c) J. Moran, A. G. Smith, R. M. Carris, J. S. Johnson, M. J. Krische, J. Am. Chem. Soc. 2011, 133, 18618;
168. d) D. Marcoux, S. R. Goudreau, A. B. Charette, J. Org. Chem. 2009, 74, 8939.
169. P.-O. Delaye, D. Didier, I. Marek, Angew. Chem. 2013, 125, 5441;
170. Angew. Chem. Int. Ed. 2013, 52, 5333
171. a) S. Harada, H. Kiyno, T. Taguchi, Y. Hanzawa, Tetrahedron Lett. 1995, 36, 9489;
172. b) Y. Hanzawa, S. Harada, R. Nishio, T. Taguchi, Tetrahedron Lett. 1994, 35, 9421.
173. a) E. Tsoglin, H. Chechik, G. Karseboom, N. Chinkov, A. Stanger, I. Marek, Adv. Synth. Catal. 2009, 351, 1005;
174. b) H. Chechik-Lankin, I. Marek, Synthesis 2005, 3311;
175. c) S. Farhat, I. Zouev, I. Marek, Tetrahedron 2004, 60, 1329.
176. B. Canchegui, P. Bertus, J. Szymoniak, Synlett 2001, 123.
177. a) G. C. Vougioukalakis, R. H. Grubbs, Chem. Rev. 2010, 110, 1746;
178. b) A. M. Lozano-Vila, S. Monsaert, A. Bajek, F. Verpoort, Chem. Rev. 2010, 110, 4865;
179. c) Metathesis in Natural Product Synthesis (Eds.: J. Cossy, S. Arsenyadis, C. Meyer), Wiley-VCH, Weinheim, 2010;
180. d) K. C. Nicolaou, P. G. Bulger, D. Sarlah, Angew. Chem. 2005, 117, 4564;
181. Angew. Chem. Int. Ed. 2005, 44, 4490;
182. e) S. T. Diver, A. J. Giessert, Chem. Rev. 2004, 104, 1317;
183. f) Handbook of Metathesis (Ed.: R. H. Grubb), Wiley-VCH, Weinheim, 2003;
184. g) A. H. Hoveyda, J. Org. Chem. 2014, 79, 4763.
185. A. H. Hoveyda, P. J. Lombardi, R. V. O'Brien, A. R. Zhugralin, J. Am. Chem. Soc. 2009, 131, 8378.
186. a) B. M. Branan, X. Wang, P. Jankowski, J. Wicha, L. A. Paquette, J. Org. Chem. 1994, 59, 6874;
187. b) J. K. Crandall, W.W. Conover, J. Org. Chem. 1978, 43, 1323;
188. c) L. E. Friedrich, R. A. Leckonby, D. M. Stout, Y.-S. P. Lam, J. Org. Chem. 1978, 43, 604;
189. d) L. E. Friedrich, R. A. Fiato, J. Org. Chem. 1974, 39, 416;
190. e) L. E. Friedrich, R. A. Fiato, J. Am. Chem. Soc. 1974, 96, 5783;
191. f) J. Ciabattoni, J. P. Kocienski, J. Am. Chem. Soc. 1971, 93, 4902;
192. g) L. E. Friedrich, R. A. Cormier, J. Org. Chem. 1970, 35, 451;
193. h) J. Ciabattoni, J. P. Kocienski, J. Am. Chem. Soc. 1969, 91, 6534.
194. Y. Gao, R. M. Hanson, J. M. Klunder, S. Y. Ko, H. Masamune, K. B. Sharpless, J. Am. Chem. Soc. 1987, 109, 5765.
195. D. Bassavaiah, B. S. Reddy, S. S. Badsara, Chem. Rev. 2010, 110, 5447.
196. A. Basheer, M. Mishima, I. Marek, Org. Lett. 2011, 13, 4076.
197. P. R. Khoury, J. D. Goddard, W. Tam, Tetrahedron 2004, 60, 8103.
198. R. D. Bach, O. Dmitrenko, J. Am. Chem. Soc. 2004, 126, 4444.
199. a) T. Seiser, T. Saget, D. N. Tran, N. Cramer, Angew. Chem. 2011, 123, 7884;
200. Angew. Chem. Int. Ed. 2011, 50, 7740;
201. b) J. C. Namyslo, D. E. Kaufmann, Chem. Rev. 2003, 103, 1485;
202. E. Lee-Ruff, G. Mladenova, Chem. Rev. 2003, 103, 1449.
203. T. Nishimura, K. Ohe, S. Uemura, J. Am. Chem. Soc. 1999, 121, 2645.
204. a) T. Nishimura, S. Uemura, J. Am. Chem. Soc. 1999, 121, 11010;
205. b) A. Schweinitz, A. Chtchemelinine, A. Orellana, Org. Lett. 2011, 13, 232;
206. c) D. Rosa, A. Chtchemelinine, A. Orellana, Synthesis 2012, 44, 1885.
207. a) S. Matsumura, Y. Maeda, T. Nishimura, S. Uemura, J. Am. Chem. Soc. 2003, 125, 8862;
208. b) T. Nishimura, S. Matsumura, Y. Maeda, S. Uemura, Chem. Commun. 2002, 50;
209. T. Nishimura, S. Matsumura, Y. Maeda, S. Uemura, Tetrahedron Lett. 2002, 43, 3037.
210. a) N. Ishida, W. Ikemoto, M. Murakami, J. Am. Chem. Soc. 2014, 136, 5912;
211. b) N. Ishida, S. Sawano, M. Murakami, Nat. Commun. 2014, 5, 3111;
212. c) L. Souillart, E. Parker, N. Cramer, Angew. Chem. 2014, 126, 3045;
213. Angew. Chem. Int. Ed. 2014, 53, 3001;
214. d) E. Parker, N. Cramer, Organometallics 2014, 33, 780;
215. e) L. Souillart, N. Cramer, Chem. Sci. 2014, 5, 837;
216. f) A. Yada, S. Fujita, M. Murakami, J. Am. Chem. Soc. 2014, 136, 7217;
217. g) T. Seiser, N. Cramer, Chem. Eur. J. 2010, 16, 3383;
218. h) T. Seiser, O. A. Roth, N. Cramer, Angew. Chem. 2009, 121, 6438;
219. Angew. Chem. Int. Ed. 2009, 48, 6320;
220. i) M. Shigeno, T. Yamamoto, M. Murakami, Chem. Eur. J. 2009, 15, 12929;
221. j) T. Seiser, N. Cramer, Angew. Chem. 2008, 120, 9435;
222. Angew. Chem. Int. Ed. 2008, 47, 9294.
223. a) T. Seiser, N. Cramer, J. Am. Chem. Soc. 2010, 132, 5340;
224. b) N. Cramer, T. Seiser, Synlett 2011, 4, 449.
225. T. Matsuda, M. Shigeno, M. Makino, M. Murakami, Org. Lett. 2006, 8, 3379.
226. a) H. Yu, C. Wang, Y. Yang, Z.-M. Dang, Chem. Eur. J. 2014, 20, 3839;
227. b) L. Ding, N. Ishida, M. Murakami, K. Morokuma, J. Am. Chem. Soc. 2014, 136, 169.
228. N. Ishida, Y. Nakanishi, M. Murakami, Angew. Chem. 2013, 125, 12091;
229. Angew. Chem. Int. Ed. 2013, 52, 11875.
230. a) Y. Masuda, M. Hasegawa, M. Yamashita, K. Nozaki, N. Ishida, M. Murakami, J. Am. Chem. Soc. 2013, 135, 7142;
231. b) T. Matsuda, M. Shigeno, M. Murakami, J. Am. Chem. Soc. 2007, 129, 12086;
232. c) T. Matsuda, M. Makino, M. Murakami, Bull. Chem. Soc. Jpn. 2005, 78, 1528;
233. d) T. Matsuda, M. Makino, M. Murakami, Org. Lett. 2004, 6, 1257;
234. e) M. Murakami, T. Itahashi, Y. Ito, J. Am. Chem. Soc. 2002, 124, 13976;
235. f) M. Murakami, T. Itahashi, H. Amii, K. Takahashi, Y. Ito, J. Am. Chem. Soc. 1998, 120, 9949.
236. a) T. Nishimura, T. Yoshinaka, Y. Nishiguchi, Y. Maeda, S. Uemura, Org. Lett. 2005, 7, 2425;
237. b) T. Nishimura, Y. Nishiguchi, Y. Maeda, S. Uemura, J. Org. Chem. 2004, 69, 5342;
238. c) T. Nishimura, S. Uemura, J. Am. Chem. Soc. 2000, 122, 12049.
239. T. Nishimura, T. Katoh, K. Takatsu, R. Shintani, T. Hayashi, J. Am. Chem. Soc. 2007, 129, 14158.
240. Y. Terao, H. Wakui, T. Satoh, M. Miura, M. Nomura, J. Am. Chem. Soc. 2001, 123, 10407.
241. a) P. Jones, P. Knochel, J. Org. Chem. 1999, 64, 186;
242. b) P. Jones, N. Millot, P. Knochel, Chem. Commun. 1998, 2405;
243. c) P. Jones, P. Knochel, Chem. Commun. 1998, 2407.
244. a) M. Iwasaki, S. Hayashi, K. Hirano, H. Yorimitsu, K. Oshima, J. Am. Chem. Soc. 2007, 129, 4463;
245. b) S. Hayashi, K. Hirano, H. Yorimitsu, K. Oshima, J. Am. Chem. Soc. 2006, 128, 2210.
246. Y. Takada, S. Hayashi, K. Hirano, H. Yorimitsu, K. Oshima, Org. Lett. 2006, 8, 2515.
247. M. Sai, H. Yorimitsu, K. Oshima, Angew. Chem. 2011, 123, 3352;
248. Angew. Chem. Int. Ed. 2011, 50, 3294.
249. S. Hayashi, K. Hirano, H. Yorimitsu, K. Oshima, Org. Lett. 2005, 7, 3577.
250. a) R. Wakabayashi, D. Fujino, S. Hayashi, H. Yorimitsu, K. Oshima, J. Org. Chem. 2010, 75, 4337;
251. b) S. Hayashi, K. Hirano, H. Yorimitsu, K. Oshima, J. Am. Chem. Soc. 2007, 129, 12650.