Transition metal-catalyzed asymmetric reactions using P-chirogenic diaminophosphine oxides: DIAPHOXs

Chemical and Pharmaceutical Bulletin

Volumn 56, Issue 9, 2008, Pages 1213-1228

  Nemoto, Tetsuhiro ^a  

^a CHIBA UNIVERSITY   (Japan)

Author keywords

Asymmetric allylic substitution; Asymmetric catalysis; Chiral ligand; Diaminophosphine oxide; Iridium; Palladium

Indexed keywords

ALIPHATIC AMINE; AROMATIC AMINE; BACLOFEN; DIAMINOPHOSPHINE OXIDE; IRIDIUM; LIGAND; MALONIC ACID; NITROMETHANE; PALLADIUM; PAROXETINE; PHOSPHINE OXIDE DERIVATIVE; PRECLAMOL; TRANSITION ELEMENT; UNCLASSIFIED DRUG;

ALKYLATION; ALLYLIC REARRANGEMENT; AMINATION; ASYMMETRIC CATALYSIS; CHIRALITY; DRUG SYNTHESIS; ENANTIOSELECTIVITY; REVIEW; SUBSTITUTION REACTION;

ALKYLATION; CATALYSIS; OXIDES; PALLADIUM; PHOSPHINES; STEREOISOMERISM; TRANSITION ELEMENTS;

EID: 51349092572     PISSN: 00092363     EISSN: 13475223     Source Type: Journal    
DOI: 10.1248/cpb.56.1213     Document Type: Review

References (164)

1. For a general review, see: Ojima I., "Catalytic Asymmetric Synthesis II," Wiley-VCH, New York, 2000.
2. Barton D., Ollis W. D., "Comprehensive Organic Chemistry," Vol. 2, Part 10, ed. by Sutherland I. O., Pergammon Press, Oxford, 1979.
3. For a review, see: Dubrovina N. V., Börner A., Angew. Chem. Int. Ed., 43, 5883-5886 (2004).
4. For a review, see: Ackermann L., Synthesis, 2006, 1557-1571 (2006).
5. For a review, see: Ackermann L., Synlett, 2007, 507-526 (2007).
6. Ghaffar T., Parkins A. W., Tetrahedron Lett., 36, 8657-8660 (1995).
7. Cobley C. J., van den Heuvel M., Abbadi A., de Vries J. G., Tetrahedron Lett., 41, 2467-2470 (2000).
8. Li G. Y., Angew. Chem. Int. Ed., 40, 1513-1516(2001).
9. Yang W., Wang Y., Corte J. R., Org. Lett., 5, 3131-3134 (2003).
10. Wolf C, Lerebours R., Org. Lett., 6, 1147-1150 (2004).
11. Ackermann L., Born R., Angew. Chem. Int. Ed., 44, 2444-2447 (2005).
12. Ackermann L., Born R., Spatz J. H., Meyer D., Angew. Chem. Int. Ed., 44, 7216-7219 (2005).
13. Gavryushin A., Kofink C, Manolikakes G., Kochel P., Org, Lett., 1, 4871-874(2005).
14. Ackermann L., Althammer A., Org. Lett., 8, 3457-3460 (2006).
15. Ackermann L., Gschrei C. J., Althammer A., Riederer M., Chem. Commun., 2006, 1419-1421 (2006).
16. Lerebours R., Wolf C, J. Am. Chem. Soc., 128, 13052-13053 (2006).
17. Ackermann L., Org. Lett., 7, 3123-3125 (2005).
18. Ackermann L., Althammer A., Born R., Angew: Chem. Lnt. Ed., 45, 2619-2622(2006).
19. Xiang X.-b., Minnaard A. J., Hessen B., Feringa B. L., Duchateau A. L. L., AndrienJ.G. O., BoogerJ.A. F., de VriesJ.G., Org. Lett., 5, 1503-1506 (2003).
20. Xiang X.-b., van den Berg M., Minnaard A. J., Feringa B. L., de VriesJ.G., Tetrahedron: Asymmetry, 15, 2223-2229 (2004).
21. Dai W.-M., Yeung K. K. Y., Leung W. L., Haynes R. K., Tetrahedron: Asymmetry, 14, 2821-2826 (2003).
22. Bigeault J., Giordano L., Buono G., Angew. Chem. Int. Ed., 44, 4753-0757 (2005).
23. Drabowicz J., Lyzwa P., Omelanczuk J., Pietrusiewicz K. M., Mikolajajczyk M., Tetrahedron: Asymmetry, 10, 2757-2763 (1999).
24. Haynes R. K., Au-Yeung Y.-L., Chen W.-K., Lam W.-L., Li Z.-Y, Yeung L.-L., Chen A. S. C, Li P., Koen M., Mitchell C. R., Vonwiller S. C, Eur J. Org. Chem., 2000, 3205-3216 (2000).
25. Leyris A., Nuel D., Giordano L., Achard M., Buono G., Tetrahedron Lett., 46, 8677-8680 (2005).
26. For a review, see: Trost B. M., Crawley M. L., Chem. Rev., 103, 2921-2943 (2003).
27. For a review, see: Lu Z., Ma S., Angew. Chem. Int. Ed., 47, 258-297 (2008).
28. For a review, see: Nemoto T., Hamada Y., Chem. Rec., 7, 150-158 (2007).
29. Nemoto T., Matsumoto T., Masuda T., Hitomi T., Hatano K., Hamada Y.,J. Am. Chem. Soc., 126, 3690-3691 (2004).
30. Nemoto T., Masuda T., Matsumoto T., Hamada Y., J. Org. Chem., 70, 7172-7178(2005).
31. For a review, see: El Gihani M. T., Heaney H., Synthesis, 1998, 357-375 (1998).
32. For a review, see: Christoffers J., Mann A., Angew. Chem. Int. Ed., 40, 4591-4597(2001).
33. For a review, see: Shibasaki M., Erasmus V M. Ohshima T., Adv. Synth. Catal., 346, 1533-1552(2004).
34. For a review, see: Trost B. M., Jiang C., Synthesis, 2006, 369-396 (2006).
35. For a review, see: Shibasaki M., Kanai M., Org. Biomol. Chem., 5, 2027-2039 (2007).
36. For a representative example, see: Hayashi T., Kanehira K., Tsuchiya H., Kumada M., J. Chem. Soc. Chem. Commun., 1982, 1162-1164 (1982).
37. For a representative example, see: Sawamura M., Nagata H., Sakamoto H., Ito Y., J. Am. Chem. Soc., 114, 2586-2592 (1992).
38. For a representative example, see: Sawamura M., Sudoh M., Ito Y., J. Am. Chem. Soc., 118, 3309-3310 (1996).
39. For a representative example, see: Trost B. M., Radinov R., Grenzer E. M., J. Am. Chem. Soc., 119, 7879-7880 (1997).
40. For a representative example, see: Nakoji M., Kaneyama T., Okino T., Takemoto Y., J. Org. Chem., 67, 7418-7423 (2002).
41. For a representative example, see: Behenna D. C., Stoltz B. M., J. Am. Chem. Soc., 126, 15044-15045 (2004).
42. For a representative example, see: Trost B. M., Xu J., J. Am. Chem. Soc., 127, 2846-2847 (2005).
43. For a representative example, see: Trost B. M., Bream R. N., Xu J., Angew. Chem. Int. Ed., 45, 3109-3112 (2006).
44. For a representative example, see: Fukuda Y., Kondo K., Aoyama T., Tetrahedron lett., 48, 3389-3391 (2007).
45. Nemoto T., Fukuda T., Matsumoto T., Hitomi T., Hamada Y., Adv. Synth. Catal., 347, 1504-1506(2005).
46. For a review on secondary ligand substrate interaction, see: Sawamura M., Ito Y., Chem. Rev., 92, 857-871 (1992).
47. For a review on secondary ligand substrate interaction, see: Börner A., Ear. J. Inorg. Chem., 2001, 327-337 (2001).
48. Nemoto T., Jin L., Nakamura H., Hamada Y., Tetrahedron lett., 47, 6577-6581 (2006).
49. Genet J. P., Grisoni S., Tetrahedron lett., 29, 4543-4546 (1988).
50. Rieck H., Helmchen G., Angew. Chem. Int. Ed. Engl., 34, 2687-2689(1995).
51. UozumiY, Suzuka T., J. Org. Chem.,11, 8644-8646(2006).
52. Maki K., Kanai M., Shibasaki M., Tetrahedron, 63, 4250-257 (2007).
53. For a representative synthesis, see: Wikström H., Sanshez D., Lindberg P., Hacksell U., Arvidsson L.-E., Johansson A. M., Thorberg S.-O., Nilsson J. L. G., Svensson K., Hjorth S., Clark D., Carlsson A., J. Med. Chem., 27, 1030-1036 (1984).
54. For a representative synthesis, see: Amat M., Cantó M., Llor N., Escolano C., Molins E., Espinosa E., Bosch J., J. Org. Chem., 67, 5343-5351(2002).
55. Brice J. L., Meerdink J. E., Stahl S. S., Org. lett., 6, 1845-1848 (2004).
56. For a representative synthesis, see: Corey E. J., Zhang F.-Y, Org. lett., 2, 4257-259 (2000).
57. For a representative synthesis, see: Belda O., Lundgren S., Moberg C., Org. lett., 5, 2275-2278 (2003).
58. For a representative synthesis, see: Okino T., Hoashi Y., Furukawa T., Xu X., Takemoto Y., J. Am. Chem. Soc., 127, 119-125 (2005).
59. For a representative synthesis, see: Carpes M. J. S., Correia C. R. D., Tetrahedron lett., 43, 741-744 (2002).
60. Jin L., Nemoto T., Nakamura H., Hamada Y., Tetrahedron: Asymmetry, 19, 1106-1113(2008).
61. For an example using carbon nucleophiles, see: Hamada Y., Sakaguchi K., Hatano K., Hara O., Tetrahedron lett., 42, 1297-1299 (2001).
62. For an example using carbon nucleophiles, see: Stang A. Q., Helmchen G., Helv. Chim. Acta, 88, 2738-2746 (2005).
63. For an example using nitrogen nucleophiles, see: Mori M., Kuroda S., Zhang C.-S., Sato Y., J. Org. Chem., 62, 3263-3270 (1997).
64. For an example using nitrogen nucleophiles, see: Trost B. M., Oslob J. D., J. Am. Chem. Soc., 121, 3057-3064 (1999).
65. For an example using nitrogen nucleophiles, see: Mori M., Nishimata T., Nagasawa Y., Sato Y., Adv. Synth. Catal., 343, 34-36 (2001).
66. For an example using nitrogen nucleophiles, see: Mori M., Nakanishi D., Kajishima D., Sato Y., J. Am. Chem. Soc., 125, 9801-9807 (2003).
67. For an example using oxygen nucleophiles, see: Trost B. M., Machacek M. R., Tsui H. C., J. Am. Chem. Soc., 127, 7014-7024 (2005).
68. For an example using oxygen nucleophiles, see: Trost B. M., Tang W., Toste F. D., J. Am. Chem. Soc., 127, 14785-14803 (2005).
69. Nemoto T., Harada T., Matsumoto T., Hamada Y., Tetrahedron lett., 48, 6304-6307 (2007).
70. For a review on asymmetric synthesis of quaternary α-amino-acid derivatives, see: Cativiela C., Díaz-de-Villegas M. D., Tetrahedron: Asymmetry, 9, 3517-3599 (1998).
71. For a review on asymmetric synthesis of quaternary α-amino-acid derivatives, see: Cativiela C., Díaz-de-Villegas M. D., Tetrahedron: Asymmetry, 11, 645-732 (2000).
72. For a review on asymmetric synthesis of quaternary α-amino-acid derivatives, see: Park K.-H, Kurth M. I, Tetrahedron, 58, 8629-8659 (2002).
73. For a review on asymmetric synthesis of quaternary α-amino-acid derivatives, see: Gröger H., Chem. Rev., 103, 2795-2828 (2003).
74. For a recent leading reference of catalytic asymmetric synthesis of quaternary α-amino acid derivatives, see: Vachal P., Jacobsen E. N., Org. Lett., 2, 867-870 (2000).
75. For a recent leading reference of catalytic asymmetric synthesis of quaternary α-amino acid derivatives, see: Funabashi K., Ratni H., Kanai M., Shibasaki M., J. Am. Chem. Soc., 123, 10784-10785 (2001).
76. For a recent leading reference of catalytic asymmetric synthesis of quaternary α-amino acid derivatives, see: Masumoto S., Usuda H., Suzuki M., Kanai M., Shibasaki M., J. Am. Chem. Soc., 125, 5634-5635 (2003).
77. For a recent leading reference of catalytic asymmetric synthesis of quaternary α-amino acid derivatives, see: Sabby S., Bella M., JørgensenK. A., J.Am. Chem. Soc., 126, 8120-8121 (2004).
78. For a recent leading reference of catalytic asymmetric synthesis of quaternary α-amino acid derivatives, see: Zhuang W., Saaby S., Jørgensen K. A., Angew. Chem., Int. Ed., 43, 4476-4478 (2004).
79. For a recent leading reference of catalytic asymmetric synthesis of quaternary α-amino acid derivatives, see: Kitamura M., Shirakawa S., Maruoka K, Angew. Chem., Int. Ed., 44, 1549-1551 (2005).
80. For a recent leading reference of catalytic asymmetric synthesis of quaternary α-amino acid derivatives, see: Liu X., Li H., Deng L., Org. Lett., 7, 167-169 (2005).
81. For a recent leading reference of catalytic asymmetric synthesis of quaternary α-amino acid derivatives, see: Ooi T., Miki T., Maruoka K, Org. Lett., 7, 191-193 (2005).
82. For a recent leading reference of catalytic asymmetric synthesis of quaternary α-amino acid derivatives, see: Suri J. T., Steiner D. D., Barbas C. F., III, Org. Lett., 7, 3885-3888 (2005).
83. For a recent leading reference of catalytic asymmetric synthesis of quaternary α-amino acid derivatives, see: Balskus E. P., Jacobsen E. N., J. Am. Chem. Soc., 128, 6810-6812 (2006).
84. For a recent leading reference of catalytic asymmetric synthesis of quaternary α-amino acid derivatives, see: Mashiko T., Hara K., Tanaka D., Fujiwara Y., Kumagai N., Shibasaki M., J. Am. Chem. Soc., 129, 11342-11343 (2007).
85. For a recent leading reference of catalytic asymmetric synthesis of quaternary α-amino acid derivatives, see: Chen Z., Morimoto H., Matsunaga S., Shibasaki M., J. Am. Chem. Soc., 130, 2170-2171 (2008).
86. For a recent leading reference of catalytic asymmetric synthesis of quaternary α-amino acid derivatives, see: Singh A., Johnston J. N., J. Am. Chem. Soc., 130, 5866-5867 (2008).
87. Kuwano R., Ito Y., J. Am. Chem. Soc., 121, 3236-3237 (1999).
88. Ogasawara M., Ngo H., Sakamoto T., Takahashi T., Org. Lett., 7, 2881-2884(2005).
89. α-Acetoamido β-keto phosphonates as the nucleophiles, see: Kuwano R., Nishio, R., Ito Y., Org. Lett., 1, 837-839 (1999).
90. Azlactones are also useful nucleophiles for providing access to chiral quaternary α-amino acid derivatives, see: Trost B. M., Ariza X., Angew. Chem. Int. Ed., 36, 2635-2637 (1997).
91. Azlactones are also useful nucleophiles for providing access to chiral quaternary α-amino acid derivatives, see: Trost B. M., Dogra K., J. Am. Chem. Soc., 124, 7256-7257 (2002).
92. For a review, see: Trost B. M., Chem. Pharm. Bull., 50, 1-14 (2002).
93. For a representative example, see: Hayashi T., Yamamoto A., Ito Y., Nishioka E., Miura H., Yanagi K., J. Am. Chem. Soc., 111, 6301-6311 (1989).
94. For a representative example, see: Trost B. M., Bunt R. C., J. Am. Chem. Soc., 116, 4089-4090 (1994).
95. For a representative example, see: Evans D. A., Campos K. R., Tedrow J. S., Michael F. E., Gagné M. R., J. Org. Chem., 64, 2994-2995(1999).
96. For a representative example, see: You S.-L., Zhu X.-Z., Lou Y.-M., Hou X.-L., Dai L.-X., J. Am. Chem. Soc., 123, 7471-7472 (2001).
97. For a representative example, see: Zablocka M., Koprowski M., Donnadieu B., Majoral J.-P., Achard M., Buono G., Tetrahedron Lett., 44, 2413-2415(2003).
98. For a representative example, see: Uozumi Y., Tanaka H., Shibatomi K., Org. Lett., 6, 281-283 (2004).
99. For a representative example, see: Faller J. W., Wilt J. C., Org. Lett., 7, 633-636 (2005).
100. For a review, see: Helmchen G., Dahnz A., Dübon P., Schelwies M., WeihofenR., Chem. Commun., 2007, 675-691 (2007).
101. For an example using a Ru catalyst, see: Matsushima Y., Onitsuka K., Kondo T., Mitsudo T., Takahashi S., J. Am. Chem. Soc., 123, 10405-10406 (2001).
102. For an example using a Ni catalyst, see: Bekowitz D. B., Maiti G., Org. Lett., 6, 2661-2664 (2004).
103. Nemoto T., Masuda T., Akimoto Y., Fukuyama T., Hamada Y., Org. Lett., 7, 4447-4450 (2005).
104. 3CN to palladium metal might prevent catalyst deactivation by competitive coordination of the product, resulting in the higher reactivity compared with the cases of other solvents.
105. Nishimata T., Sato Y., Mori M., J. Org. Chem., 69, 1837-1843 (2004).
106. Nemoto T., Fukuyama T., Yamamoto E., Tamura S., Fukuda T., Matsumoto T., Akimoto Y., Hamada Y., Org. Lett., 9, 927-930 (2007).
107. For a review, see: Basavaiah D., Rao A. J., Satyanarayana T., Chem. Rev., 103, 811-891(2003).
108. For an representative example, see: Shi M., Xu Y.-M., Angew. Chem. Lnt. Ed., 41, 4507-510 (2002).
109. For an representative example, see: Shi M., Chen L.-H., Chem. Commun., 2003, 1310-1311 (2003).
110. For an representative example, see: Kawahara S., Nakano A., Esumi T., Iwabuchi Y., Hatakeyama S., Org. Lett., 5, 3103-3105 (2003).
111. For an representative example, see: Balan D., Adolfsson H., Tetrahedron Lett., 44, 2521-2524 (2003).
112. For an representative example, see: Raheen I. T., Jacobsen E. N., Adv. Synth. Catal., 347, 1701-1708 (2005).
113. For an representative example, see: Matsui K., Takizawa S., Sasai H., J.Am. Chem. Soc., 127, 3680-3681 (2005).
114. For an representative example, see: Shi M., Ma G.-N., Gao J., J. Org. Chem., 72, 9779-9781 (2007).
115. For an representative example, see: Takizawa S., Matsui K., Sasai H., J. Synth. Org. Chem. Jpn., 65, 1089-1098 (2007).
116. Trost B. M., Tsui H.-C., Toste F. D., J. Am. Chem. Soc., 122, 3534-3535 (2000).
117. Trost B. M., Thiel O. R., Tsui H.-C., J. Am. Chem. Soc., 124, 11616-11617(2002).
118. Trost B. M., Thiel O. R., Tsui H.-C., J. Am. Chem. Soc., 125, 13155-13164(2003).
119. For a review, see: Cheng R. P., Gellman S. H., DeGrado W F., Chem. Rev., 101, 3219-3232 (2001).
120. Tang W., Wu S., Zhang X., J. Am. Chem. Soc., 125, 9570-9571 (2003).
121. Mita T., Fujimori I., Wada R., Wen J., Kanai M., Shibasaki M., J. Am. Chem. Soc., 127, 11252-11253 (2005).
122. Seebach D., Estermann H., Tetrahedron Lett., 28, 3103-3106 (1987).
123. Nemoto T., Tamura S., Sakamoto T., Hamada Y., Tetrahedron Asymmetry, 19, 1751-1759(2008).
124. Dong Y., Teesdale-Spittle P., Hoberg J. O., Tetrahedron Lett., 46, 353-355 (2005).
125. For the pioneering work on Ir-catalyzed allylic substitutions, see: Takeuchi R., Kashio M., Angew. Chem. Lnt. Ed. Engl., 36, 263-265 (1997).
126. For the pioneering work on Ir-catalyzed allylic substitutions, see: Takeuchi R., Kashio M., J. Am. Chem. Soc., 120, 8647-8655 (1998).
127. For the pioneering work on Ir-catalyzed allylic substitutions, see: Takeuchi R., Ue N., Tanabe K., Yamashita K., Shiga N., J. Am. Chem. Soc., 123, 9525-9534 (2001).
128. Nemoto T., Sakamoto T., Matsumoto T., Hamada Y., Tetrahedron Lett., 47, 8737-8740 (2006).
129. For a representative example of Ir-catalyzed asymmetric allylic amination, see: Ohmura T., Hartwig J. F., J. Am. Chem. Soc., 124, 15164-15165(2002).
130. For a representative example of Ir-catalyzed asymmetric allylic amination, see: Kiener C A., Shu C., Incarvito C., Hartwig J. F., J. Am. Chem. Soc., 125, 14272-14273 (2003).
131. For a representative example of Ir-catalyzed asymmetric allylic amination, see: Shu C., Leiner A., Hartwig J. F., Angeiw Chem. Lnt. Ed., 43, 4797-800 (2004).
132. For a representative example of Ir-catalyzed asymmetric allylic amination, see: Tissot-Croset K., Polet D., Alexakis A., Angew. Chem. Lnt. Ed., 43, 2426-2428 (2004).
133. For a representative example of Ir-catalyzed asymmetric allylic amination, see: Lipowsky G., Helmchen G., Chem. Commun., 2004, 896-897 (2004).
134. For a representative example of Ir-catalyzed asymmetric allylic amination, see: Miyabe H., Matsumura A., Moriyama K., Takemoto Y., Org. Lett., 6, 4631-4634 (2004).
135. For a representative example of Ir-catalyzed asymmetric allylic amination, see: Weihohen R., Dahnz A., Tverskoy O., Helmchen G., Chem. Commun., 2005, 3541-3543 (2005).
136. For a representative example of Ir-catalyzed asymmetric allylic amination, see: Polet D., Alexakis A., Org. Lett., 7, 1621-1624 (2005).
137. For a representative example of Ir-catalyzed asymmetric allylic amination, see: Weihohen R., Tverskoy O., Helmchen G., Angew. Chem. Lnt. Ed., 45, 5546-5549 (2006).
138. For a representative example of Ir-catalyzed asymmetric allylic amination, see: Pouy M. J., Leitner A., Weix D. J., Ueno S., HartwigJ.F., Org. Lett., 9, 3949-3952 (2007).
139. Although the role of hexafluorophosphate anion is unkown, we speculate that a cationic iridium complex might be formed by the anion exchange between hexafluorophosphate ion and a coordinated species around the Ir metal, resulting in the increased reactivity.
140. Nemoto T., Sakamoto T., Fukuyama T., Hamada Y., Tetrahedron Lett., 48, 4977-4981 (2007).
141. For a representative example of Ir-catalyzed asymmetric allylic alkylation, see: Xanssen J. P., Helmchen G., Tetrahedron Lett., 38, 8025-8026(1997).
142. For a representative example of Ir-catalyzed asymmetric allylic alkylation, see: Bartels A., Helmchen G., Chem. Commun., 1999, 741-742(1999).
143. For a representative example of Ir-catalyzed asymmetric allylic alkylation, see: Fuji K., Kinoshita N., Tanaka K., Kawabata T., Chem. Commun., 1999, 2289-2290 (1999).
144. For a representative example of Ir-catalyzed asymmetric allylic alkylation, see: Kanayama T., Yoshida K., Miyabe H., Takemoto Y., Angew. Chem. Lnt. Ed., 42, 2054-2056 (2003).
145. For a representative example of Ir-catalyzed asymmetric allylic alkylation, see: Kanayama T., Yoshida K., Miyabe H., Kimachi T., Takemoto Y., J. Org. Chem., 68, 6197-6201 (2003).
146. For a representative example of Ir-catalyzed asymmetric allylic alkylation, see: Kinoshita N., Marx K. H., Tanaka K., Tsubaki K., Kawabata T., Yoshikai N., Nakamura E., Fuji K., J. Org. Chem., 69, 7960-7964 (2004).
147. For a representative example of Ir-catalyzed asymmetric allylic alkylation, see: Alexakis A., Polet D., Org. Lett., 6, 3529-3532 (2004).
148. For a representative example of Ir-catalyzed asymmetric allylic alkylation, see: Lipowsky G., Miller N., Helmchen G., Angew. Chem. Int. Ed., 43, 4595-4597 (2004).
149. For a representative example of Ir-catalyzed asymmetric allylic alkylation, see: Streiff S., Welter C., Schelwiss M., Lipowsky G., Miller N., Helmchen G., Chem. Commun., 2005, 2957-2959 (2005).
150. For a representative example of Ir-catalyzed asymmetric allylic alkylation, see: Graening T., Hartwig J. F., J. Am. Chem. Soc., 127, 17192-17193(2005).
151. For a representative example of Ir-catalyzed asymmetric allylic alkylation, see: Polet D., Alexakis A., Tissot-Croset K., Corminboeuf C., Ditrich K., Chem. Eur. J., 12, 3596-3609 (2006).
152. For a representative example of Ir-catalyzed asymmetric allylic etherification, see: Shu C., Hartwig J. F., Angew. Chem. Int. Ed., 43, 4794-4797 (2004).
153. For a representative example of Ir-catalyzed asymmetric allylic etherification, see: Lyothier I., Defieber C., Carreira E. M., Angew. Chem. Int. Ed., 45, 6204-6207 (2006).
154. For a representative example of Ir-catalyzed asymmetric allylic etherification, see: Kimura M., Uozumi Y., J. Org. Chem., 72, 707-714 (2007).
155. For a representative example of Ir-catalyzed asymmetric allylic etherification, see: Ueno S., Hartwig J. F., Angew. Chem. Int. Ed., 47, 1928-1931(2008).
156. For a catalytic asymmetric synthesis of paroxetine, see: Senda T., Ogasawara M., Hayashi T., J. Org. Chem., 66, 6852-6856 (2001).
157. For a catalytic asymmetric synthesis of paroxetine, see: Taylor M. S., JacobsenE.N., J. Am. Chem. Soc., 125, 11204-11205(2003).
158. For a catalytic asymmetric synthesis of paroxetine, see: Hughes G., Kimura M., Buchwald S. L., J. Am. Chem. Soc., 125, 11253-11258 (2003).
159. For a catalytic asymmetric synthesis of paroxetine, see: Brandau S., Landa A., Franzén J., Marigo M., Jørgensen K. A., Angew. Chem. Int. Ed., 45, 4305-4309 (2006).
160. For a catalytic asymmetric synthesis of paroxetine, see: Koech P. K., Krische M. J., Tetrahedron, 62, 10594-10602 (2006).
161. For a catalytic asymmetric synthesis of paroxetine, see: Ito M., Sakaguchi A., Kobayashi C., Ikariya T., J. Am. Chem. Soc., 129, 290-291 (2007).
162. For a catalytic asymmetric synthesis of paroxetine, see: Bower J. F., Riis-Johannessen T., Szeto P., Whitehead A. J., Gallagher T., Chem. Commun., 2007, 728-730 (2007).
163. For a catalytic asymmetric synthesis of paroxetine, see: Hynes P. S., Stupple P. A., Dixon D. J., Org. lett., 10, 1389-1391 (2008).
164. Evans D. A., Fu G. C., Hoveyda A. H., J. Am. Chem. Soc., 114, 6671-6679(1992).