Asymmetric cyanation with the Chiral Ru-Li combined catalysts

Synlett

Volumn 23, Issue 13, 2012, Pages 1865-1881

  Ohkuma, Takeshi ^a   Kurono, Nobuhito ^a  

^a HOKKAIDO UNIVERSITY   (Japan)

Author keywords

, unsaturated ketones; aldehydes; asymmetric catalysis; cyanosilylation; hydrocyanation; imines; lithium; ruthenium

Indexed keywords

ALDEHYDE; ALDIMINE DERIVATIVE; ALPHA KETO ESTER; AMINO ACID DERIVATIVE; ESTER DERIVATIVE; IMINE; KETONE; LITHIUM; PHENYLGLYCINATE; RUTHENIUM; UNCLASSIFIED DRUG;

ARTICLE; ASYMMETRIC CYANATION; CATALYSIS; CATALYST; CHEMICAL MODIFICATION; CHEMICAL REACTION; CHIRALITY; COMPLEX FORMATION; CYANATION; CYANOSILYLATION; ENANTIOSELECTIVITY; HYDROCYANATION; REACTION ANALYSIS; SPECTROSCOPY; STRECKER TYPE REACTION;

EID: 84863979873     PISSN: 09365214     EISSN: 14372096     Source Type: Journal    
DOI: 10.1055/s-0032-1316545     Document Type: Article

References (171)

1. North M. Synlett: 1993; 807
2. Effenberger F. Angew. Chem., Int. Ed. Engl.: 1994; 33 1555
3. Gregory RJ. H. Chem. Rev.: 1999; 99 3649
4. Enders D, Shilvock JP. Chem. Soc. Rev.: 2000; 29 359
5. Yet L. Angew. Chem. Int. Ed.: 2001; 40 875
6. Shibasaki M, Kanai M, Funabashi K. Chem. Commun.: 2002; 1989
7. North M. Tetrahedron: Asymmetry: 2003; 14 147
8. Gröger H. Chem. Rev.: 2003; 103 2796
9. Kanai M, Shibasaki M. In Multimetallic Catalysts in Organic Synthesis. Shibasaki M, Yamamoto Y. Wiley-VCH Weinheim: 2004; 103
10. Brunel J.-M, Holmes IP. Angew. Chem. Int. Ed.: 2004; 43 2752
11. Kanai M, Kato N, Ichikawa E, Shibasaki M. Synlett: 2005; 1491
12. Achard TR. J, Clutterbuck LA, North M. Synlett: 2005; 1828
13. Chen F.-X, Feng X. Curr. Org. Synth.: 2006; 3 77
14. Taylor MS, Jacobsen EN. Angew. Chem. Int. Ed.: 2006; 45 1520
15. Shibasaki M, Kanai M. Org. Biomol. Chem.: 2007; 5 2027
16. Shibasaki M, Kanai M, Mita T. Org. React.: 2008; 70 1
17. Khan NH, Kureshy RI, Abdi SH. R, Agrawal S, Jasra RV. Coord. Chem. Rev.: 2008; 252 593
18. North M, Usanov DL, Young C. Chem. Rev.: 2008; 108 5146
19. Gawronski J, Wascinska N, Gajewy J. Chem. Rev.: 2008; 108 5227
20. Merino P, Marqués-López E, Tejero T, Herrera RP. Tetrahedron: 2009; 65 1219
21. Wang W, Liu X, Lin L, Feng X. Eur. J. Org. Chem.: 2010; 4751
22. Martens J. ChemCatChem: 2010; 2 379
23. Bergin E. In Science of Synthesis: Stereoselective Synthesis. Vol. 2 Molander GA. Thieme Stuttgart: 2010; 531
24. Wang J, Liu X, Feng X. Chem. Rev.: 2011; 111 6947
25. Evans DA, Truesdale LK, Carroll GL. J. Chem. Soc., Chem. Commun.: 1973; 55
26. Lidy W, Sundermeyer W. Chem. Ber.: 1973; 106 587
27. Noyori R, Murata S, Suzuki M. Tetrahedron: 1981; 37 3899
28. Greenlee WJ, Hangauer DG. Tetrahedron Lett.: 1983; 24 4559
29. Vougioukas AE, Kagan HB. Tetrahedron Lett.: 1987; 28 5513
30. Reetz MT, Drewes MW, Harms K, Reif W. Tetrahedron Lett.: 1988; 29 3295
31. Faller JW, Gundersen L.-L. Tetrahedron Lett.: 1993; 34 2275
32. Scholl M, Fu GC. J. Org. Chem.: 1994; 59 7178
33. Cozzi PG, Floriani C. J. Chem. Soc., Perkin Trans. 1: 1995; 2557
34. Whitesell JK, Apodaca R. Tetrahedron Lett.: 1996; 37 2525
35. Yang Y, Wang D. Synlett: 1997; 1379
36. Komatsu N, Uda M, Suzuki H, Takahashi T, Domae T, Wada M. Tetrahedron Lett.: 1997; 38 7215
37. Loh T.-P, Xu K.-C, Ho DS.-C, Sim K.-Y. Synlett: 1998; 369
38. Saravanan P, Anand RV, Singh VK. Tetrahedron Lett.: 1998; 39 3823
39. Bandini M, Cozzi PG, Garelli A, Melchiorre P, Unami-Ronchi A. Eur. J. Org. Chem.: 2002; 3243
40. King JB, Gabbai FP. Organometallics: 2003; 22 1275
41. Córdoba R, Plumet J. Tetrahedron Lett.: 2003; 44 6157
42. Baleizão C, Gigante B, Garcia H, Corma A. Tetrahedron Lett.: 2003; 44 6813
43. Karimi B, Ma'Mani L. Org. Lett.: 2004; 6 4813
44. Evans DA, Truesdale LK. Tetrahedron Lett.: 1973; 4929
45. Ohta H, Hayakawa S, Moriwaki H, Harada S, Okamoto M. Chem. Pharm. Bull.: 1986; 34 4916
46. Kobayashi S, Tsuchida Y, Mukaiyama T. Chem. Lett.: 1991; 537
47. Matsubara S, Takai T, Utimoto K. Chem. Lett.: 1991; 1447
48. Ruble JC, Fu GC. J. Org. Chem.: 1996; 61 7230
49. Kantam ML, Sreekanth P, Santhi PL. Green. Chem.: 2000; 47
50. Wilkinson HS, Grover PT, Vandedbossche CP, Bakale RP, Bhongle NN, Wald SA, Senanayake CH. Org. Lett.: 2001; 3 553
51. Wang Z, Fetterly B, Verkade JG. J. Organomet. Chem.: 2002; 646 161
52. Kim SS, Rajagopal G, Song DG. J. Organomet. Chem.: 2004; 689 1734
53. Reetz MT, Fox DN. A. Tetrahedron Lett.: 1993; 34 1119
54. Azizi N, Saidi MR. J. Organomet. Chem.: 2003; 688 283
55. Foley LH. Synth. Commun.: 1984; 14 1291
56. Vtazankina OA, Gostevskii BA, Vyazankin NS. J. Organomet. Chem.: 1985; 292 145
57. Cohen VL, Gibson RE, Fan LH, De La Cruz R, Gitler MS, Hariman E, Reba RC. J. Med. Chem.: 1991; 34 2989
58. Amurrio I, Córdova R, Csák AG, Plumet J. Tetrahedron: 2004; 60 10521
59. Arai N, Ooka H, Azuma K, Yabuuchi T, Kurono N, Inoue T, Ohkuma T. Org. Lett.: 2007; 9 939
60. Arai N, Azuma K, Nii N, Ohkuma T. Angew. Chem. Int. Ed.: 2008; 47 7457
61. Ooka H, Arai N, Azuma K, Kurono N, Ohkuma T. J. Org. Chem.: 2008; 73 9084
62. Reetz MT, Kunisch F, Heitmann P. Tetrahedron Lett.: 1986; 27 4721
63. Kobayashi S, Tsuchiya Y, Mukaiyama T. Chem. Lett.: 1991; 541
64. Hayashi M, Miyamoto Y, Inoue T, Oguni N. J. Org. Chem.: 1993; 58 1515
65. Corey EJ, Wang Z. Tetrahedron Lett.: 1993; 34 4001
66. Hamashima Y, Sawada D, Kanai M, Shibasaki M. J. Am. Chem. Soc.: 1999; 121 2641
67. Belokon YN, Caveda-Cepas S, Green B, Ikonnikov NS, Khrustalev VN, Larichev VS, Moscalenko MA, North M, Orizu C, Tararov VI, Tasinazzo M, Timofeeva GI, Yashkina LV. J. Am. Chem. Soc.: 1999; 121 3968
68. Belokon YN, North M, Parsons T. Org. Lett.: 2000; 2 1617
69. You J.-S, Gau H.-M, Choi MC. K. Chem. Commun.: 2000; 1963
70. Hamashima Y, Sawada D, Nogami H, Kanai M, Shibasaki M. Tetrahedron: 2001; 57 805
71. Chang C.-W, Yang C.-T, Hwang C.-D, Uang B.-J. Chem. Commun.: 2002; 54
72. Li Y, He B, Qin B, Feng X, Zhang G. J. Org. Chem.: 2004; 69 7910
73. Ryu DH, Corey EJ. J. Am. Chem. Soc.: 2004; 126 8106
74. Qin Y.-C, Liu L, Pu L. Org. Lett.: 2005; 7 2381
75. Belokon YN, Maleev VI, North M, Usanov DL. Chem. Commun.: 2006; 4614
76. Belokon YN, Clegg W, Harrington RW, Young C, North M. Tetrahedron: 2007; 63 5287
77. Zhang Z, Wang Z, Zhang B, Ding K. Angew. Chem. Int. Ed.: 2010; 49 6746
78. Belokon YN, Green B, Ikonnikov NS, North M, Tararov VI. Tetrahedron Lett.: 1999; 40 8147
79. Hamashima Y, Kanai M, Shibasaki M. J. Am. Chem. Soc.: 2000; 122 7412
80. Hamashima Y, Kanai M, Shibasaki M. Tetrahedron Lett.: 2001; 42 691
81. Belokon YN, Green B, Ikonnikov NS, North M, Parsons T, Tararov VI. Tetrahedron: 2001; 57 771
82. Shen Y, Feng X, Zhang G, Jiang Y. Synlett: 2002; 1353
83. Chen F, Feng X, Qin B, Zhang G, Jiang Y. Org. Lett.: 2003; 5 949
84. Fujii K, Maki K, Kanai M, Shibasaki M. Org. Lett.: 2003; 5 733
85. Shen Y, Feng X, Li Y, Zhang G, Jiang Y. Eur. J. Org. Chem.: 2004; 129
86. He B, Chen F.-X, Li Y, Feng X, Zhang G. Eur. J. Org. Chem.: 2004; 4657
87. Xiong Y, Huang X, Gou S, Huang J, Wen Y, Feng X. Adv. Synth. Catal.: 2006; 348 538
88. Shen K, Liu X, Li Q, Feng X. Tetrahedron: 2008; 64 147
89. Yoshinaga K, Nagata T. Adv. Synth. Catal.: 2009; 351 1495; see also ref. 1l
90. Yabu K, Masumoto S, Yamasaki S, Hamashima Y, Kanai M, Du W, Curran DP, Shibasaki M. J. Am. Chem. Soc.: 2001; 123 9908
91. Yabu K, Masumoto S, Kanai M, Curran DP, Shibasaki M. Tetrahedron Lett.: 2002; 43 2923
92. Masumoto S, Suzuki M, Kanai M, Shibasaki M. Tetrahedron Lett.: 2002; 43 8647
93. Yabu K, Masumoto S, Kanai M, Du W, Curran DP, Shibasaki M. Heterocycles: 2003; 59 369
94. Masumoto S, Suzuki M, Kanai M, Shibasaki M. Tetrahedron: 2004; 60 10497
95. Deng H, Isler MP, Snapper ML, Hoveyda AH. Angew. Chem. Int. Ed.: 2002; 41 1009
96. Chen F.-X, Zhou H, Liu X, Qin B, Feng X, Zhang G, Jiang Y. Chem.-Eur. J.: 2004; 10 4790
97. Ryu DH, Corey EJ. J. Am. Chem. Soc.: 2005; 127 5384
98. Kim SS, Kwak JM. Tetrahedron: 2006; 62 49
99. Alaaeddine A, Roisnel T, Thomas CM, Carpentier J.-F. Adv. Synth. Catal.: 2008; 350 731
100. Cao J.-J, Zhou F, Zhou J. Angew. Chem. Int. Ed.: 2010; 49 4976
101. North M, Omedes-Pujou M, Williamson C. Chem.-Eur. J.: 2010; 16 11367
102. Liu X, Qin B, Zhou X, He B, Feng X. J. Am. Chem. Soc.: 2005; 127 12224
103. Hatano M, Ikeno T, Matsumura T, Torii S, Ishihara K. Adv. Synth. Catal.: 2008; 350 1776
104. Tian S.-K, Hong R, Deng L. J. Am. Chem. Soc.: 2003; 125 9900
105. Fuerst DE, Jacobsen EN. J. Am. Chem. Soc.: 2005; 127 8964
106. Qin B, Liu X, Shi J, Zheng K, Zhao H, Feng X. J. Org. Chem.: 2007; 72 2374
107. Zuend SJ, Jacobsen EN. J. Am. Chem. Soc.: 2007; 129 15872
108. Gröger H. Adv. Synth. Catal.: 2001; 343 547
109. Garcia-Urdiales E, Alfonso I, Gotor V. Chem. Rev.: 2005; 105 313
110. Griengl H, Schwab H, Fechter M. Trends Biotechnol.: 2000; 18 252
111. Sharma M, Sharma NN, Bhalla TC. Enzyme Microb. Technol.: 2005; 37 279
112. Oku J, Inoue S. J. Chem. Soc.: 1981; 229
113. Tanaka K, Mori A, Inoue S. J. Org. Chem.: 1990; 55 181
114. Jackson WR, Jayatilake GS, Matthews BR, Wilshire C. Aust. J. Chem.: 1988; 41 203
115. Danda H. Synlett: 1991; 263
116. Danda H, Nishikawa H, Otaka K. J. Org. Chem.: 1991; 56 6740
117. North M. Tetrahedron: 1992; 48 5509
118. Shvo Y, Gal M, Becker Y, Elgavi A. Tetrahedron: Asymmetry: 1996; 7 911
119. Kogut EF, Thoen JC, Lipton MA. J. Org. Chem.: 1998; 63 4604
120. Schoenebeck F, Houk KN. J. Org. Chem.: 2009; 74 1464
121. Abe H, Nitta H, Mori A, Inoue S. Chem. Lett.: 1992; 2443
122. Nitta H, Yu D, Kudo M, Mori A, Inoue S. J. Am. Chem. Soc.: 1992; 114 7969
123. Tanaka Y, Kanai M, Shibasaki M. J. Am. Chem. Soc.: 2008; 130 6072
124. Tanaka Y, Kanai M, Shibasaki M. J. Am. Chem. Soc.: 2010; 132 8862
125. Sammis GM, Jacobsen EN. J. Am. Chem. Soc.: 2003; 125 4442
126. Sammis GM, Danjo H, Jacobsen EN. J. Am. Chem. Soc.: 2004; 126 9928
127. Mazet C, Jacobsen EN. Angew. Chem. Int. Ed.: 2008; 47 1762
128. Madhavan N, Weck M. Adv. Synth. Catal.: 2008; 350 419
129. Mita T, Sasaki K, Kanai M, Shibasaki M. J. Am. Chem. Soc.: 2005; 127 514
130. Fujimori I, Mita T, Maki K, Shiro M, Sato A, Furusho S, Kanai M, Shibasaki M. Tetrahedron: 2007; 63 5820
131. Bernardi L, Fini F, Fochi M, Ricci A. Synlett: 2008; 1857
132. Wang J, Li W, Liu Y, Chu Y, Lin L, Liu X, Feng X. Org. Lett.: 2010; 12 1280
133. Iyer MS, Gigstad KM, Namdev ND, Lipton M. J. Am. Chem. Soc.: 1996; 118 4910
134. Sigman MS, Jacobsen EN. J. Am. Chem. Soc.: 1998; 120 4901
135. Corey EJ, Grogan MJ. Org. Lett.: 1999; 1 157
136. Sigman MS, Vachal P, Jacobsen EN. Angew. Chem. Int. Ed.: 2000; 39 1279
137. Vachal P, Jacobsen EN. J. Am. Chem. Soc.: 2002; 124 10012
138. Jiao Z, Feng X, Liu B, Chen F, Zhang G, Jiang Y. Eur. J. Org. Chem.: 2003; 3818
139. Huang J, Corey EJ. Org. Lett.: 2004; 6 5027
140. Ooi T, Uematsu Y, Maruoka K. J. Am. Chem. Soc.: 2006; 128 2548
141. Rueping M, Sugiono E, Azap C. Angew. Chem. Int. Ed.: 2006; 45 2617
142. Herrera RP, Sgarzani V, Bernardi L, Fini F, Pettersen D, Ricci A. J. Org. Chem.: 2006; 71 9869
143. Pan SC, Zhou J, List B. Angew. Chem. Int. Ed.: 2007; 46 612
144. Ooi T, Uematsu Y, Fujimoto J, Fukumoto K, Maruoka K. Tetrahedron Lett.: 2007; 48 1337
145. Wen Y, Xiong Y, Chang L, Huang J, Liu X, Feng X. J. Org. Chem.: 2007; 72 7715
146. Negru M, Schollmeyer D, Kunz H. Angew. Chem. Int. Ed.: 2007; 46 9339
147. Wen Y, Gao B, Fu Y, Dong S, Liu X, Feng X. Chem.-Eur. J.: 2008; 14 6789
148. Zuend SJ, Coughlin MP, Lalonds MP, Jacobsen EN. Nature: 2009; 461 968
149. Zamfir A, Tsogoeva SB. Org. Lett.: 2010; 12 188
150. Ishitani H, Komiyama S, Kobayashi S. Angew. Chem. Int. Ed.: 1998; 37 3186
151. Sigman MS, Jacobsen EN. J. Am. Chem. Soc.: 1998; 120 5315
152. Crueger CA, Kuntz KW, Dzierba CD, Wirschun WG, Gleason JD, Snapper ML, Hoveyda AH. J. Am. Chem. Soc.: 1999; 121 4284
153. Ishitani H, Komiyama S, Hasegawa Y, Kobayashi S. J. Am. Chem. Soc.: 2000; 122 762
154. Takamura M, Hamashima Y, Usuda H, Kanai M, Shibasaki M. Angew. Chem. Int. Ed.: 2000; 39 1650
155. Porter JR, Wirschun WG, Kuntz KW, Snapper ML, Hoveyda AH. J. Am. Chem. Soc.: 2000; 122 2657
156. Keith JM, Jacobsen EN. Org. Lett.: 2004; 6 153
157. Banphavichit V, Mansawat W, Bhanthumnavin W, Vilaivan T. Tetrahedron: 2004; 60 10559
158. Blacker J, Clutterbuck LA, Crampton MR, Grosjean C, North M. Tetrahedron: Asymmetry: 2006; 17 1449
159. Wang J, Hu X, Jiang J, Dou S, Huang X, Liu X, Feng X. Angew. Chem. Int. Ed.: 2007; 46 8468
160. Nakamura S, Nakashima H, Sugimoto H, Sano H, Hattori M, Shibata N, Toru T. Chem.-Eur. J.: 2008; 14 2145
161. Hatano M, Hattori Y, Furuya Y, Ishihara K. Org. Lett.: 2009; 11 2321
162. Banphavichit V, Mansawat W, Bhanthumnavin W, Vilaivan T. Tetrahedron: 2009; 65 5849
163. Wang J, Wang W, Li W, Hu X, Shen K, Tan C, Liu X, Feng X. Chem.-Eur. J.: 2009; 15 11642
164. Abell JP, Yamamoto H. J. Am. Chem. Soc.: 2009; 131 15118
165. Seayad AM, Ramalingam B, Yoshinaga K, Nagata T, Chai CL. L. Org. Lett.: 2010; 12 264
166. Kaur P, Pindi S, Wever W, Rajale T, Li G. J. Org. Chem.: 2010; 75 5144
167. Karimi B, Maleki A, Elhamifar D, Clark JH, Hunt AJ. Chem. Commun.: 2010; 46 6947
168. Petrini M. Chem. Rev.: 2005; 105 3949
169. Tillman AL, Ye J, Dixon DJ. Chem. Commun.: 2006; 1191
170. Dixon DA, Hertler WR, Chase DB, Farnham WB, Davidson F. Inorg. Chem.: 1988; 27 4012
171. Sassaman MB, Prakash GK. S, Olah GA. J. Org. Chem.: 1990; 55 2016