Recent advances in transition-metal-catalyzed intermolecular carbomagnesiation and carbozincation

Beilstein Journal of Organic Chemistry

Volumn 9, Issue , 2013, Pages 278-302

  Murakami, Kei ^a   Yorimitsu, Hideki ^a,b  

^a KYOTO UNIVERSITY   (Japan)

^b JAPAN SCIENCE AND TECHNOLOGY AGENCY   (Japan)

Author keywords

Alkene; Alkyne; Carbomagnesiation; Carbometalation; Carbozincation; Transition metal

Indexed keywords

EID: 84874618992     PISSN: None     EISSN: 18605397     Source Type: Journal    
DOI: 10.3762/bjoc.9.34     Document Type: Review

References (136)

1. Grignard, V. C. R. Hebd. Seances Acad. Sci. 1900, 130, 1322-1324.
2. Lee, J.; Velarde-Ortiz, R.; Guijarro, A.; Wurst, J. R.; Rieke, R. D. J. Org. Chem. 2000, 65, 5428-5430. doi:10.1021/jo000413i (Pubitemid 30666461)
3. Piller, F. M.; Appukkuttan, P.; Gavryushin, A.; Helm, M.; Knochel, P. Angew. Chem. 2008, 120, 6907-6911. doi:10.1002/ange.200801968
4. Angew. Chem., Int. Ed. 2008, 47, 6802-6806. doi:10.1002/anie.200801968
5. Knochel, P.; Almena Perea, J. J.; Jones, P. Tetrahedron 1998, 54, 8275-8319. doi:10.1016/S0040-4020(98)00318-4 (Pubitemid 28294229)
6. Majid, T. N.; Knochel, P. Tetrahedron Lett. 1990, 31, 4413-4416. doi:10.1016/S0040-4039(00)97635-4 (Pubitemid 20229454)
7. Zhu, L.; Wehmeyer, R. M.; Rieke, R. D. J. Org. Chem. 1991, 56, 1445-1453. doi:10.1021/jo00004a021
8. Krasovskiy, A.; Malakhov, V.; Gavryushin, A.; Knochel, P. Angew. Chem. 2006, 118, 6186-6190. doi:10.1002/ange.200601450
9. Angew. Chem., Int. Ed. 2006, 45, 6040-6044. doi:10.1002/anie.200601450 (Pubitemid 44408697)
10. Walborsky, H. M. Acc. Chem. Res. 1990, 23, 286-293. doi:10.1021/ ar00177a004
11. Ren, H.; Krasovskiy, A.; Knochel, P. Org. Lett. 2004, 6, 4215-4217. doi:10.1021/ol048363h
12. Knochel, P.; Dohle, W.; Gommermann, N.; Kneisel, F. F.; Kopp, F.; Korn, T.; Sapountzis, I.; Vu, V. A. Angew. Chem. 2003, 115, 4438-4456. doi:10.1002/ange.200300579
13. Angew. Chem. Int. Ed. 2003, 42, 4302-4320. doi:10.1002/anie.200300579 (Pubitemid 37221310)
14. Ila, H.; Baron, O.; Wagner, A. J.; Knochel, P. Chem. Commun. 2006, 583-593. doi:10.1039/b510866g
15. Inoue, A.; Kitagawa, K.; Shinokubo, H.; Oshima, K. J. Org. Chem. 2001, 66, 4333-4339. doi:10.1021/jo015597v (Pubitemid 32867574)
16. Kitagawa, K.; Inoue, A.; Shinokubo, H.; Oshima, K. Angew. Chem. 2000, 112, 2594-2596. doi:10.1002/1521-3757(20000717)112:142594::AID-ANGE25943.0. CO;2-O
17. Angew. Chem. Int. Ed. 2000, 39, 2481-2483. doi:10.1002/1521- 3773(20000717)39:142481::AID-ANIE24813.0.C O;2-J
18. Normant, J. F.; Alexakis, A. Synthesis 1981, 841-870. doi:10.1055/s-1981-29622 (See for carbometalation reactions (including Mg, Zn, Li, Cu, Al) of various alkynes and alkenes.)
19. Oppolzer, W. Angew. Chem. 1989, 101, 39-53. doi:10.1002/ange.19891010106
20. Angew. Chem. Int. Ed. Engl. 1989, 28, 38-52. doi:10.1002/anie.198900381 (See for intramolecular metallo-ene reaction using stoichiometric Li, Mg, Zn and catalytic Ni, Pd, Pt.)
21. Yamamoto, Y.; Asao, N. Chem. Rev. 1993, 93, 2207-2293. doi:10.1021/cr00022a010 (See for selective reaction using allylic metals, including allylmagnesiation and allylzincation.)
22. Marek, I. J. Chem. Soc., Perkin Trans. 1 1999, 535-544. doi:10.1039/A807060A (See for asymmetric carbometalation, including carbomagnesiation and carbozincation.)
23. Fallis, A. G.; Forgione, P. Tetrahedron 2001, 57, 5899-5913. doi:10.1016/S0040-4020(01)00422-7 (See for metal-mediated carbometalation (including Mg, Zn, Bi, Cu, Zr, Li, Si, Sn, In, B, Ga, Al, Ni, Mn) of alkynes and alkenes containing adjacent heteroatoms.) (Pubitemid 32607595)
24. Shinokubo, H.; Oshima, K. Catal. Surv. Asia 2003, 7, 39-46. doi:10.1023/A:1023432624548 (See for manganese-catalyzed carbomagnesiation.) (Pubitemid 38076838)
25. Shinokubo, H.; Oshima, K. Eur. J. Org. Chem. 2004, 2081-2091. doi:10.1002/ejoc.200300757 (See for transition-metal-catalyzed carbon-carbon bond formation with organomagnesium reagents, including carbomagnesiation.)
26. Flynn, A. B.; Ogilvie, W. W. Chem. Rev. 2007, 107, 4698-4745. doi:10.1021/cr050051k (See for stereocontrolled synthesis of tetrasubstituted olefins, including carbomagnesiation and carbozincation.) (Pubitemid 350225864)
27. Pérez-Luna, A.; Botuha, C.; Ferreira, F.; Chemla, F. New J. Chem. 2008, 32, 594-606. doi:10.1039/B716292H (See for uncatalyzed carbometalation of alkenes with zinc enolates.) (Pubitemid 351473897)
28. Terao, J.; Kambe, N. Bull. Chem. Soc. Jpn. 2006, 79, 663-672. doi:10.1246/bcsj.79.663 (See for transition metal-catalyzed C-C bond formation reactions using alkyl halides, including titanium-catalyzed carbomagnesiation.) (Pubitemid 44689497)
29. Marek, I. Chem.-Eur. J. 2008, 14, 7460-7468. doi:10.1002/chem.200800580 (See for an interesting application of carbometalation intermediates to stereoselective reactions.)
30. Basheer, A.; Marek, I. Beilstein J. Org. Chem. 2010, 6, No. 77. doi:10.3762/bjoc.6.77 (See for a recent review on carbocupration of heteroatom-substituted alkynes including copper-catalyzed and copper-mediated reactions.)
31. Nakamura, E.; Yoshikai, N. J. Org. Chem. 2010, 75, 6061-6067. doi:10.1021/jo100693m (See for iron-catalyzed carbon-carbon bond formation, including carbomagnesiation and carbozincation.)
32. Negishi, E. Angew. Chem. 2011, 123, 6870-6897. doi:10.1002/ange.201101380
33. Angew. Chem. Int. Ed. 2011, 50, 6738-6764. doi:10.1002/anie.201101380 (See for Nobel Lecture by Negishi, including carbozincation).
34. Knochel, P. Carbometallation of Alkenes and Alkynes. In Additions to and Substitutions at C-C π-Bonds;
35. Trost, B.; Fleming, I.; Semmelhack, M. F., Eds.; Comprehensive Organic Synthesis, Vol. 4; Pergamon Press: New York, 1991; pp 865-911. doi:10.1016/B978-0-08-052349-1.00111-6
36. Marek, I.; Normant, J.-F. In Metal-Catalyzed Cross-Coupling Reactions; Diederich, F.; Stang, P. J., Eds.; Wiley-VCH: Weinheim, 1998; pp 271-337.
37. Wakefield, B. J. Addition of Organomagnesium Compounds to Carbon-Carbon Multiple Bonds. Organomagnesium Methods in Organic Synthesis; Academic Press: San Diego, 1995; pp 73-86. doi:10.1016/B978-012730945-3.50006-2
38. Marek, I.; Chinkov, N.; Banon-Tenne, D. Carbometallation Reactions. In Metal-Catalyzed Cross-Coupling Reactions, 2nd ed.; de Meijere, A.; Diederich, F., Eds.; Wiley-VCH: Weinheim, 2004; pp 395-478. doi:10.1002/9783527619535.ch7
39. Itami, K.; Yoshida, J.-I. Carbomagnesiation Reactions. In The Chemistry of Organomagnesium Compounds; Rappoport, Z.; Marek, I., Eds.; Wiley: Chichester, 2008; pp 631-679. doi:10.1002/9780470751879.ch14
40. Lorthiois, E.; Meyer, C. Carbozincation of Alkenes and Alkynes. Patai's Chemistry of Functional Groups; Wiley: Ney York, 2009; online. doi:10.1002/9780470682531.pat0382
41. Bretting, C.; Munch-Petersen, J.; Jørgensen, P. M.; Refn, S. Acta Chem. Scand. 1960, 14, 151-156. doi:10.3891/acta.chem.scand.14-0151
42. Corey, E. J.; Katzenellenbogen, J. A. J. Am. Chem. Soc. 1969, 91, 1851-1852. doi:10.1021/ja01035a045
43. Siddall, J. B.; Biskup, M.; Fried, J. H. J. Am. Chem. Soc. 1969, 91, 1853-1854. doi:10.1021/ja01035a046
44. Yoshikai, N.; Nakamura, E. Chem. Rev. 2012, 112, 2339-2372. doi:10.1021/cr200241f
45. Konno, T.; Daitoh, T.; Noiri, A.; Chae, J.; Ishihara, T.; Yamanaka, H. Tetrahedron 2005, 61, 9391-9404. doi:10.1016/j.tet.2005.07.022 (See for regio-and stereoselective carbocupration of internal acetylenes activated by perfluoroalkyl groups.) (Pubitemid 41206500)
46. Xie, M.; Huang, X. Synlett 2003, 477-480. doi:10.1055/s-2003-37524
47. Xie, M.; Liu, L.; Wang, J.; Wang, S. J. Organomet. Chem. 2005, 690, 4058-4062. doi:10.1016/j.jorganchem.2005.06.006 (Pubitemid 41350819)
48. Sklute, G.; Bolm, C.; Marek, I. Org. Lett. 2007, 9, 1259-1261. doi:10.1021/ol070070b
49. Xie, M.; Lin, G.; Zhang, J.; Ming, L.; Feng, C. J. Organomet. Chem. 2010, 695, 882-886. doi:10.1016/j.jorganchem.2010.01.003
50. Maezaki, N.; Sawamoto, H.; Yoshigami, R.; Suzuki, T.; Tanaka, T. Org. Lett. 2003, 5, 1345-1347. doi:10.1021/ol034289b (Pubitemid 37162079)
51. Maezaki, N.; Sawamoto, H.; Suzuki, T.; Yoshigami, R.; Tanaka, T. J. Org. Chem. 2004, 69, 8387-8393. doi:10.1021/jo048747l (Pubitemid 39557203)
52. Sklute, G.; Amsallem, D.; Shabli, A.; Varghese, J. P.; Marek, I. J. Am. Chem. Soc. 2003, 125, 11776-11777. doi:10.1021/ja036872t (Pubitemid 37175386)
53. Sklute, G.; Marek, I. J. Am. Chem. Soc. 2006, 128, 4642-4649. doi:10.1021/ja060498q
54. Marek, I.; Sklute, G. Chem. Commun. 2007, 1683-1691. doi:10.1039/b615042j (Pubitemid 46652239)
55. Kolodney, G.; Sklute, G.; Perrone, S.; Knochel, P.; Marek, I. Angew. Chem. 2007, 119, 9451-9454. doi:10.1002/ange.200702981
56. Angew. Chem., Int. Ed. 2007, 46, 9291-9294. doi:10.1002/anie.200702981 (Pubitemid 350292161)
57. Das, J. P.; Chechik, H.; Marek, I. Nat. Chem. 2009, 1, 128-132. doi:10.1038/nchem.131
58. Dutta, B.; Gilboa, N.; Marek, I. J. Am. Chem. Soc. 2010, 132, 5588-5589. doi:10.1021/ja101371x
59. Das, J. P.; Marek, I. Chem. Commun. 2011, 47, 4593-4623. doi:10.1039/c0cc05222a
60. Mejuch, T.; Botoshansky, M.; Marek, I. Org. Lett. 2011, 13, 3604-3607. doi:10.1021/ol201221d
61. Mejuch, T.; Dutta, B.; Botoshansky, M.; Marek, I. Org. Biomol. Chem. 2012, 10, 5803-5806. doi:10.1039/c2ob25121c
62. Minko, Y.; Pasco, M.; Lercher, L.; Botoshansky, M.; Marek, I. Nature 2012, 490, 522-526. doi:10.1038/nature11569
63. Hayashi, T.; Inoue, K.; Taniguchi, N.; Ogasawara, M. J. Am. Chem. Soc. 2001, 123, 9918-9919. doi:10.1021/ja0165234 (Pubitemid 32929408)
64. Hayashi, T.; Yamasaki, K. Chem. Rev. 2003, 103, 2829-2844. doi:10.1021/cr020022z
65. Sakai, M.; Hayashi, H.; Miyaura, N. Organometallics 1997, 16, 4229-4231. doi:10.1021/om9705113
66. Takaya, Y.; Ogasawara, M.; Hayashi, T.; Sakai, M.; Miyaura, N. J. Am. Chem. Soc. 1998, 120, 5579-5580. doi:10.1021/ja980666h (Pubitemid 28305327)
67. Shintani, R.; Hayashi, T. Org. Lett. 2005, 7, 2071-2073. doi:10.1021/ol0506819 (Pubitemid 40732051)
68. Richey, H. G., Jr.; Rothman, A. M. Tetrahedron Lett. 1968, 9, 1457-1460. doi:10.1016/S0040-4039(01)98978-6
69. Forgione, P.; Fallis, A. G. Tetrahedron Lett. 2000, 41, 11-15. doi:10.1016/S0040-4039(99)01994-2
70. Duboudin, J.-G.; Jousseaume, B.; Saux, A. J. Organomet. Chem. 1979, 168, 1-11. doi:10.1016/S0022-328X(00)91989-2
71. Anastasia, L.; Dumond, Y. R.; Negishi, E. Eur. J. Org. Chem. 2001, 3039-3043. doi:10.1002/1099-0690(200108)2001:163039::AID-EJOC30393.0.C O;2-V
72. Zhang, D.; Ready, J. M. J. Am. Chem. Soc. 2006, 128, 15050-15051. doi:10.1021/ja0647708 (Pubitemid 44853494)
73. Okada, K.; Oshima, K.; Utimoto, K. J. Am. Chem. Soc. 1996, 118, 6076-6077. doi:10.1021/ja960791y (Pubitemid 26236832)
74. Nishimae, S.; Inoue, R.; Shinokubo, H.; Oshima, K. Chem. Lett. 1998, 785-786. doi:10.1246/cl.1998.785
75. Murakami, K.; Ohmiya, H.; Yorimitsu, H.; Oshima, K. Chem. Lett. 2007, 36, 1066-1067. doi:10.1246/cl.2007.1066
76. Wong, T.; Tjepkema, M. W.; Audrain, H.; Wilson, P. D.; Fallis, A. G. Tetrahedron Lett. 1996, 37, 755-758. doi:10.1016/0040-4039(95)02303-8 (See for anti-vinylmagnesiation of propargyl alcohol in the absence of transition-metal catalyst.) (Pubitemid 26047056)
77. Itami, K.; Kamei, T.; Yoshida, J. J. Am. Chem. Soc. 2003, 125, 14670-14671. doi:10.1021/ja037566i (Pubitemid 37475535)
78. Normant, J. F.; Alexakis, A.; Commercon, A.; Cahiez, G.; Villieras, J.; Normant, J. F. C. R. Seances Acad. Sci., Ser. C 1974, 279, 763-765.
79. Vermeer, P.; de Graaf, C.; Meijer, J. Recl. Trav. Chim. Pays-Bas 1974, 93, 24-25. doi:10.1002/recl.19740930111
80. Meijer, J.; Westmijze, H.; Vermeer, P. Recl. Trav. Chim. Pays-Bas 1976, 95, 102-104. doi:10.1002/recl.19760950504
81. Alexakis, A.; Cahiez, G.; Normant, J. F.; Villieras, J. Bull. Soc. Chim. Fr. 1977, 693-698.
82. Chechik-Lankin, H.; Marek, I. Org. Lett. 2003, 5, 5087-5089. doi:10.1021/ol036154b (Pubitemid 38073005)
83. Chechik-Lankin, H.; Livshin, S.; Marek, I. Synlett 2005, 2098-2100. doi:10.1055/s-2005-871962 (Pubitemid 41207621)
84. Levin, A.; Basheer, A.; Marek, I. Synlett 2010, 329-332. doi:10.1055/s-0029-1219221 (See for regiodivergent carbocupration of ynol ether derivatives.)
85. Gourdet, B.; Lam, H. W. J. Am. Chem. Soc. 2009, 131, 3802-3803. doi:10.1021/ja900946h
86. Gourdet, B.; Rudkin, M. E.; Watts, C. A.; Lam, H. W. J. Org. Chem. 2009, 74, 7849-7858. doi:10.1021/jo901658v
87. Yasui, H.; Yorimitsu, H.; Oshima, K. Chem. Lett. 2007, 36, 32-33. doi:10.1246/cl.2007.32
88. Yasui, H.; Yorimitsu, H.; Oshima, K. Bull. Chem. Soc. Jpn. 2008, 81, 373-379. doi:10.1246/bcsj.81.373
89. Watkins, E. K.; Richey, H. G., Jr. Organometallics 1992, 11, 3785-3794. doi:10.1021/om00059a048
90. Nakamura, M.; Hirai, A.; Nakamura, E. J. Am. Chem. Soc. 2000, 122, 978-979. doi:10.1021/ja983066r (Pubitemid 30094419)
91. Nakamura, M.; Inoue, T.; Sato, A.; Nakamura, E. Org. Lett. 2000, 2, 2193-2196. doi:10.1021/ol005892m (See for enantioselective allylzincation of cyclopropenone acetal with an allylic zinc reagent bearing a chiral bisoxazoline ligand.)
92. Liao, L.; Fox, J. M. J. Am. Chem. Soc. 2002, 124, 14322-14323. doi:10.1021/ja0278234 (Pubitemid 35403751)
93. Yan, N.; Liu, X.; Fox, J. M. J. Org. Chem. 2008, 73, 563-568. doi:10.1021/jo702176x (Pubitemid 351437416)
94. Simaan, S.; Marek, I. Org. Lett. 2007, 9, 2569-2571. doi:10.1021/ ol070974x
95. Simaan, S.; Masarwa, A.; Bertus, P.; Marek, I. Angew. Chem. 2006, 118, 4067-4069. doi:10.1002/ange.200600556
96. Angew. Chem., Int. Ed. 2006, 45, 3963-3965. doi:10.1002/anie.200600556 (Pubitemid 44105698)
97. Yang, Z.; Xie, X.; Fox, J. M. Angew. Chem. 2006, 118, 4064-4066. doi:10.1002/ange.200600531
98. Angew. Chem. Int. Ed. 2006, 45, 3960-3962. doi:10.1002/anie.200600531 (Pubitemid 44105697)
99. Simaan, S.; Masarwa, A.; Zohar, E.; Stanger, A.; Bertus, P.; Marek, I. Chem.-Eur. J. 2009, 15, 8449-8464. doi:10.1002/chem.200901074
100. Liu, X.; Fox, J. M. J. Am. Chem. Soc. 2006, 128, 5600-5601. doi:10.1021/ja058101q (Pubitemid 43724339)
101. Tarwade, V.; Liu, X.; Yan, N.; Fox, J. M. J. Am. Chem. Soc. 2009, 131, 5382-5383. doi:10.1021/ja900949n
102. Tarwade, V.; Selvaraj, R.; Fox, J. M. J. Org. Chem. 2012, 77, 9900-9904. doi:10.1021/jo3019076
103. Krämer, K.; Leong, P.; Lautens, M. Org. Lett. 2011, 13, 819-821. doi:10.1021/ol1029904
104. Lautens, M.; Hiebert, S. J. Am. Chem. Soc. 2004, 126, 1437-1447. doi:10.1021/ja037550s (Pubitemid 38200813)
105. Terao, J.; Tomita, M.; Singh, S. P.; Kambe, N. Angew. Chem. 2010, 122, 148-151. doi:10.1002/ange.200904721
106. Angew. Chem., Int. Ed. 2010, 49, 144-147. doi:10.1002/anie.200904721
107. Liu, Y.; Ma, S. Chem. Sci. 2011, 2, 811-814. doi:10.1039/C0SC00584C (See for an interesting uncatalyzed reaction of 2-cyclopropenecarboxylates with organomagnesium reagents to afford tri-and tetrasubstituted alkenes by carbon-carbon bond cleavage.)
108. Wang, Y.; Fordyce, E. A. F.; Chen, F. Y.; Lam, H. W. Angew. Chem. 2008, 120, 7460-7463. doi:10.1002/ange.200802391
109. Angew. Chem. Int. Ed. 2008, 47, 7350-7353. doi:10.1002/anie.200802391 (See for iron-catalyzed carboalumination/ring-opening sequence of cyclopropenes.)
110. Duboudin, J. G.; Jousseaume, B.; Saux, A. J. Organomet. Chem. 1978, 162, 209-222. doi:10.1016/S0022-328X(00)82039-2
111. Stüdemann, T.; Knochel, P. Angew. Chem. 1997, 109, 132-134. doi:10.1002/ange.19971090142
112. Angew. Chem. Int. Ed. Engl. 1997, 36, 93-95. doi:10.1002/anie.199700931
113. Stüdemann, T.; Ibrahim-Ouali, M.; Knochel, P. Tetrahedron 1998, 54, 1299-1316. doi:10.1016/S0040-4020(97)10226-5 (Pubitemid 28044305)
114. Cann, R. O.; Waltermire, R. E.; Chung, J.; Oberholzer, M.; Kasparec, J.; Ye, Y. K.; Wethman, R. Org. Process Res. Dev. 2010, 14, 1147-1152. doi:10.1021/op100112r
115. Yorimitsu, H.; Tang, J.; Okada, K.; Shinokubo, H.; Oshima, K. Chem. Lett. 1998, 27, 11-12. doi:10.1246/cl.1998.11
116. Yamagami, T.; Shintani, R.; Shirakawa, E.; Hayashi, T. Org. Lett. 2007, 9, 1045-1048. doi:10.1021/ol063132r
117. Shirakawa, E.; Ikeda, D.; Masui, S.; Yoshida, M.; Hayashi, T. J. Am. Chem. Soc. 2012, 134, 272-279. doi:10.1021/ja206745w
118. Ilies, L.; Yoshida, T.; Nakamura, E. J. Am. Chem. Soc. 2012, 134, 16951-16954. doi:10.1021/ja307631v
119. Negishi, E.; Van Horn, D. E.; Yoshida, T.; Rand, C. L. Organometallics 1983, 2, 563-565. doi:10.1021/om00076a021
120. Negishi, E.; Miller, J. A. J. Am. Chem. Soc. 1983, 105, 6761-6763. doi:10.1021/ja00360a060
121. Horn, D. E. V.; Negishi, E. J. Am. Chem. Soc. 1978, 100, 2252-2254. doi:10.1021/ja00475a058
122. Suginome, M.; Shirakura, M.; Yamamoto, A. J. Am. Chem. Soc. 2006, 128, 14438-14439. doi:10.1021/ja064970j (Pubitemid 44749826)
123. Daini, M.; Suginome, M. Chem. Commun. 2008, 5224-5226. doi:10.1039/b809433k
124. Shirakawa, E.; Yamasaki, K.; Yoshida, H.; Hiyama, T. J. Am. Chem. Soc. 1999, 121, 10221-10222. doi:10.1021/ja992597s (Pubitemid 29526727)
125. Shirakawa, E.; Yamagami, T.; Kimura, T.; Yamaguchi, S.; Hayashi, T. J. Am. Chem. Soc. 2005, 127, 17164-17165. doi:10.1021/ja0542136 (Pubitemid 41791018)
126. Matsumoto, A.; Ilies, L.; Nakamura, E. J. Am. Chem. Soc. 2011, 133, 6557-6559. doi:10.1021/ja201931e
127. Murakami, K.; Ohmiya, H.; Yorimitsu, H.; Oshima, K. Org. Lett. 2007, 9, 1569-1571. doi:10.1021/ol0703938
128. Murakami, K.; Yorimitsu, H.; Oshima, K. Org. Lett. 2009, 11, 2373-2375. doi:10.1021/ol900883j
129. Tan, B.-H.; Dong, J.; Yoshikai, N. Angew. Chem. 2012, 124, 9748-9752. doi:10.1002/ange.201204388
130. Angew. Chem. Int. Ed. 2012, 51, 9610-9614. doi:10.1002/anie.201204388
131. Corpet, M.; Gosmini, C. Chem. Commun. 2012, 48, 11561-11563. doi:10.1039/c2cc36676b
132. Murakami, K.; Yorimitsu, H.; Oshima, K. Chem.-Eur. J. 2010, 16, 7688-7691. doi:10.1002/chem.201001061
133. Nishikawa, T.; Yorimitsu, H.; Oshima, K. Synlett 2004, 1573-1574. doi:10.1055/s-2004-829086
134. Yasui, H.; Nishikawa, T.; Yorimitsu, H.; Oshima, K. Bull. Chem. Soc. Jpn. 2006, 79, 1271-1274. doi:10.1246/bcsj.79.1271 (Pubitemid 44689489)
135. Kambe, N.; Moriwaki, Y.; Fujii, Y.; Iwasaki, T.; Terao, J. Org. Lett. 2011, 13, 4656-4659. doi:10.1021/ol2018664
136. Fujii, Y.; Terao, J.; Kambe, N. Chem. Commun. 2009, 1115-1117. doi:10.1039/b820521c