Iminium ylides from carbenes and carbenoids: Generation and synthetic applications

Russian Chemical Reviews

Volumn 74, Issue 2, 2005, Pages 171-192

  Khlebnikov, A F ^a   Novikov, M S ^a   Kostikov, R R ^a  

^a ST PETERSBURG STATE UNIVERSITY   (Russian Federation)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 27644497439     PISSN: 0036021X     EISSN: 14684837     Source Type: Journal    
DOI: 10.1070/RC2005v074n02ABEH000973     Document Type: Review

References (163)

1. A Padwa, S F Hornbuckle Chem. Rev. 91 263 (1991)
2. A F Khlebnikov, M S Novikov, R R Kostikov Adv. Heterocyct. Chem. 65 93 (1996)
3. M S Novikov, A F Khlebnikov, in Sovremennye Problemy Organicheskoi Khimii (Modern Problems of Organic Chemistry) (Leningrad: Leningrad State University, 1991) Vol. 10, p. 69
4. a
5. T Ye, M A McKervey Chem. Rev. 94 1091 (1994)
6. b
7. G Bucher, J C Scaiano, M S Platz, in Kinetics of Carbene Reactions in Solution Vol. 18, Subvol. E2 (Berlin: Springer, 1998) p. 141
8. R L Barcus, L M Hadel, L J Johnston, M S Platz, T G Savino, J C Scaiano J. Am. Chem. Soc. 108 3928 (1986)
9. R Bonneau, M T H Liu J. Am. Chem. Soc. 113 9872 (1991)
10. K Fernamberg, J R Snoonian, M S Platz Tetrahedron Lett. 42 8761 (2001)
11. L M Hadel, M S Platz, J C Scaiano Chem. Phys. Leu. 97 446 (1983)
12. R L Barcus, B B Wright, M S Platz, J C Scaiano Tetrahedron Lett. 24 3955 (1983)
13. D Griller, L Hadel, A S Nazran, M S Platz, P C Wong, J C Scaiano J. Am. Chem. Soc. 106 2227 (1984)
14. J E Jackson, M S Platz, in Advances in Carbene Chemistry Vol. 1 (Ed. U Brinker) (Greenwich: JAI Press, 1994) p. 89
15. A Padwa, M D Weingarten Chem. Rev. 96 223 (1996)
16. J E Jackson, N Soundararajan, M S Platz, M T H Liu J. Am. Chem. Soc. 110 5595 (1988)
17. M S Platz, W R White III, D A Modarelli, S A Celebi Res. Chem. Int. 175 (1994)
18. E M Tippmann, M S Platz J. Phys. Chem. A 107 8547 (2003)
19. J E Chateauneuf, R P Johnson, M M Kirchhoff J. Am. Chem. Soc. 112 3217 (1990)
20. M Robert, J R Snoonian, M S Platz, G X Wu, H Hong, D M Thamattoor, M Jones J. Phys. Chem. A 102 587 (1998)
21. M T H Liu, R Bonneau J. Am. Chem. Soc. 111 6873 (1989)
22. R Bonneau, M T H Liu, M T Rayez J. Am. Chem. Soc. 111 5973 (1989)
23. G J Ho, K Krogh-Jespersen, R A Moss, S Shen, R S Sheridan, R Subramanian J. Am. Chem. Soc. 111 6875 (1989)
24. M T H Liu, R Bonneau J. Phys. Chem. 93 7298 (1989)
25. R A Moss, W Liu, K Krogh-Jespersen J. Phys. Chem. 97 13 413 (1993)
26. R A Moss, G-J Ho Tetrahedron Lett. 31 1225 (1990)
27. R A Moss, G-J Ho J. Am. Chem. Soc. 112 5642 (1990)
28. J E Jackson, N Soundararajan, W White, M T H Liu, R Bonneau, M S Platz J. Am. Chem. Soc. 111 6874 (1989)
29. M T H Liu, R Bonneau J. Am. Chem. Soc. 112 3915 (1990)
30. N Soundararajan, M S Platz, J E Jackson, M P Doyle, S-M Oon, M T H Liu, S M Anand J. Am. Chem. Soc. 110 7143 (1988)
31. M T H Liu, R Bonneau J. Am. Chem. Soc. 114 3604 (1992)
32. C-S Ge, E G Jang, E A Jefferson, W G Liu, R A Moss, J Wlostowska, S Xue J. Chem. Soc., Chem. Commun. 1479 (1994)
33. M B Jones, J E Jackson, N Soundararajan, M S Platz J. Am. Chem. Soc. 110 5597 (1988)
34. R A Moss, W Lawrynowicz, N J Turro, I R Gould, Y Cha J. Am. Chem. Soc. 108 7028 (1986)
35. N J Turro, J A Butcher, R A Moss, W Guo, R C Munjal, M Fedorynski J. Am. Chem. Soc. 102 7576 (1980)
36. M B Jones, M S Platz J. Org. Chem. 56 1694 (1991)
37. R Bonneau, M T H Liu, R Lapouyade J. Chem. Soc., Perkin Trans. 1 1547 (1989)
38. S Celebi, M L Tsao, M S Platz J. Phys. Chem. A 105 1158 (2001)
39. Y Sun, I Likhotvorik, M S Platz Tetrahedron Lett. 43 7 (2002)
40. I Likhotvorik, Z Zhu, E L Tae, E Tippmann, B T Hill, M S Platz J. Am. Chem. Soc. 123 6061 (2001)
41. A Vasella, K Briner, N Soundararajan, M S Platz J. Org. Chem. 56 4741 (1991)
42. R A Moss, T Zdrojewski, G-J Ho J. Chem. Soc., Chem. Commun. 946 (1991)
43. R A Moss, S Xue, W G Liu, K Krogh-Jespersen J. Am. Chem. Soc. 118 12588 (1996)
44. R A Moss, S Xue, W Liu J. Am. Chem. Soc. 116 1583 (1994)
45. H M Perrin, W R White, M S Platz Tetrahedron Lett. 32 4443 (1991)
46. D R Boate, L J Johnston, P C Kwong, E Lee-Ruff, J C Scaiano J. Am. Chem. Soc. 112 8858 (1990)
47. J-L Wang, J P Toscano, M S Platz, V Nikolaev. V Popik J. Am. Chem. Soc. 117 5477 (1995)
48. M Robert, J P Toscano, M S Platz, S C Abbot, M M Kirchhoff, R P Johnson J. Phys. Chem. 100 18 426 (1996)
49. J P Toscano, M S Platz, V Nikolaev J. Am. Chem. Soc. 117 4712 (1995)
50. J P Toscano, M S Platz, V Nikolaev, V Popik J. Am. Chem. Soc. 116 8146 (1994)
51. D A Modarelli, M S Platz, R S Sheridan, J R Ammann J. Am. Chem. Soc. 115 10 440 (1993)
52. A Admasu, M S Platz, A Marcinek, J Michalak, A D Gudmundsdottir, J Gebicki J. Phvs. Org. Chem. 10 207 (1997)
53. A Admasu, A D Gudmundsdottir, M S Platz J. Phys. Chem. 101 3832 (1997)
54. E L Tae, C Ventre, Z Zhu, I Likhotvorik, F Ford, E Tippmann, M S Platz J. Phys. Chem. A 105 10 146 (2001)
55. D A Modarelli, M S Platz J. Am. Chem. Soc. 113 8985 (1991)
56. D A Modarelli, S Morgan, M S Platz J. Am. Chem. Soc. 114 7034 (1992)
57. F Ford, T Yuzawa, M S Platz , S Matzinger, M Fmlscher J. Am. Chem. Soc. 120 4430 (1998)
58. E L Tae, Z Zhu, M S Platz, J P Pezacki, J Warkentin J. Phys. Chem. A 103 5336 (1999)
59. S Morgan, J E Jackson, M S Platz J. Am. Chem. Soc. 113 2782 (1991)
60. W R White, M S Platz, N Chen, M Jones Jr J. Am. Chem. Soc. 112 7794 (1990)
61. N Chen, M Jones Jr , W R White, M S Platz J. Am. Chem. Soc. 113 4981 (1991)
62. M H Sugiyama, S Celebi, M S Platz J. Am. Chem. Soc. 114 966 (1992)
63. A Admasu, A D Gudmundsdottir, M S Platz, D S Watt, S Kwiatkowski, P J Crocker J. Chem. Soc., Perkin Trans. 2 1093 (1998)
64. Y Takahashi, M Inaba, H Tomioka, in The International Symposium on Reactive Intermediate, Nara, Japan, 2001 p. 93
65. Y Takahashi, A Nicolaides, H Tomioka J. Synth. Org. Jpn. 59 1070 (2001)
66. J E Jackson, N Soundararajan, M S Platz Tetrahedron Lett. 30 1335 (1989)
67. J E Chateauneuf, M T H Liu J. Org. Chem. 56 5942 (1991)
68. R Bonneau, Y N Romashin, M T H Liu J. Photochem. Photobiol. A: Chem. 126 31 (1999)
69. A Kuhn, C Plüg, C Wentrup J. Am. Chem. Soc. 122 1945 (2000)
70. M B Jones, M S Platz Tetrahedron Lett. 31 953 (1990)
71. H Tomioka, J Nakajima, H Mizuno, T Sone, K Hikai J. Am. Chem. Soc. 117 11 355 (1995)
72. P Baret, H Buffet, J-L Pierre Bull. Soc. Chim. Fr. 2493 (1972)
73. L Casarrubios, J A Perez, M Brookhart, J L Templeton J. Org. Chem. 61 8358 (1996)
74. T Akiyama, S Ogi, K Fuchibe Tetrahedron Lett. 44 4011 (2003)
75. B Crousse, S Narizuka, D Bonnet-Delpon, J-P Begue Chem. Lett. 679 (2001)
76. H-J Ha, J-M Suh, K-H Kang, Y-G Ahn, O Han Tetrahedron 54 851 (1998)
77. K G Rasmussen, R G Jørgensen J. Chem. Soc., Perkin Trans. 1 1287 (1997)
78. K G Rasmussen, R G Hazell, R G Jorgensen Acta Chem. Scand. 52 1056 (1998)
79. K G Rasmussen, K Juhl, R G Hazell, R G Jørgensen J. Chem. Soc., Perkin Trans. 2 1347 (1998)
80. K G Rasmussen, K A Jorgensen J. Chem. Soc., Chem. Commun. 1401 (1995)
81. W Sun, C-G Xia, H-W Wang Tetrahedron Lett. 44 2409 (2003)
82. S Nagayama, S Kobayashi Chem. Lett. 685 (1998)
83. W Xie, J Fang, J Li, P G Wang Tetrahedron 55 12929 (1999)
84. K B Hansen, N S Finney, E N Jacobsen Angew. Chem., Int. Ed. Engl. 34 676 (1995)
85. M F Mayer, M M Hossain J. Org. Chem. 63 6839 (1998)
86. T B Gunnoe, P S White, J L Templeton, L Casarrubios J. Am. Chem. Soc. 119 3171 (1997)
87. J C Antilla, W D Wulff J. Am. Chem. Soc. 121 5099 (1999)
88. C Loncaric, W D Wulff Org. Lett. 3 3675 (2001)
89. M Moran, G Bernardinelli, P Müller Helv. Chim. Acta 78 2048 (1995)
90. J M Mohan, B S Uphade, V R Choudhary, T Ravindranathan, A Sudalai Chem. Commun. 1429 (1997)
91. J R Krumper, M Gerisch, J M Suh, R J Bergman, T D Tilley J. Org. Chem. 68 9705 (2003)
92. M P Doyle, W Hu, D J Timmons Org. Lett. 3 933 (2001)
93. Z Zhu, J H Espenson J. Org. Chem. 60 7090 (1995)
94. Z Zhu, J H Espenson J. Am. Chem. Soc. 118 9901 (1996)
95. J H Espenson Chem. Commun. 479 (1999)
96. G-Y Li, J Chen, W-Y Yu, W Hong, C-M Che Org. Lett. 5 2153 (2003)
97. C V Galliford, M A Beenen, S T Nguyen, K A Scheldt Org. Lett. 5 3487 (2003)
98. M P Doyle, W Hu, D J Timmons Org. Lett. 3 3741 (2001)
99. M P Doyle, M Yan, W Hu, L S Gronenberg J. Am. Chem. Soc 125 4692 (2003)
100. A Padwa, D C Dean, M H Osterhout, L Precedo, M A Semones J. Org. Chem. 59 5347 (1994)
101. A M Mara, O Singh, E J Thomas, D J Williams J. Chem. Soc., Perkin Trans. 1 2169 (1982)
102. A Padwa, D J Austin, L Precedo, L Zhi J. Org. Chem. 58 1144 (1993)
103. A Padwa, D C Dean J. Org. Chem. 55 405 (1990)
104. M C McMills, D L Wright, J D Zubkowski, E J Valente Tetrahedron Lett. 37 7205 (1996)
105. R Bartnik, G Mloston Tetrahedron 40 2569 (1984)
106. R Bonneau, Y N Romashin, M T H Liu, S E MacPherson J. Chem. Soc., Chem. Commun. 509 (1994)
107. M T H Liu, Y N Romashin, R Bonneau Int. J. Chem. Kinet. 26 1179 (1994)
108. Y N Romashin, M T H Liu, S S Nijjar, O A Attanasi Chem. Commun. 1147 (2000)
109. Y N Romashin, M T H Liu, R Bonneau Chem. Commun. 447 (1999)
110. Y N Romashin, M T H Liu, W Ma, R A Moss Tetrahedron Lett. 40 7163 (1999)
111. c
112. J A Deyrup, in Small Ring Heterocycles (Ed. A Hassner) (New York: Interscience, 1983) p. 1
113. R R Kostikov, A F Khlebnikov, V Y Bespalov J. Phys. Org. Chem. 6 83 (1993)
114. d
115. d
116. d
117. A F Khlebnikov, M S Novikov, R R Kostikov Synlett 929 (1997)
118. d
119. A F Khlebnikov, T Yu Nikiforova, I V Polikarpova, R R Kostikov, in Mezhfaznyi Kataliz: Mekhanizm i Primenenie í Organicheskom Sinteze (Tez. Dokl. Mezhdunarodnogo Simpoziuma), S-Peterburg, 1997 [Phase-Transfer Catalysis: Mechanism and Application in Organic Synthesis (Abstracts of Reports of International Symposium) St Retersburg, 1997] p. 57
120. d
121. d
122. c
123. c
124. d
125. A F Khlebnikov, E I Kostik, R R Kostikov Synthesis 568 (1993)
126. B Bachowska Monatsh. Chem. 126 227 (1996)
127. K Berg-Nielson Acta Chem. Scand., Ser. B 31 224 (1977)
128. E I Kostik, Candidate Thesis in Chemical Sciences, Institute of Technical Chemistry, Urals Branch of Russian Academy of Sciences, Perm', 1997
129. c
130. J S Ro, D S Iyengar, U T Bhalerao, S N Rao Heterocycles 26 1161 (1987)
131. d
132. c
133. d
134. d
135. d
136. d
137. d
138. M S Novikov, A F Khlebnikov, A A Stepanov, R R Kostikov Synthesis 782 (1994)
139. d
140. d
141. d
142. T Yu Nikiforova, in Sovremennye Problemy Organicheskoi Khimii (Modern Problems of Organic Chemistry) (St Petersburg: St Petersburg State University, 1998) Vol. 12, p. 98
143. D Seyferth, G Murphy J. Organomet. Chem. 49 117 (1973)
144. d
145. D L S Brahms, W P Dailey Chem. Rev. 96 1585 (1996)
146. J R McCarthy, C L Barney, M J O'Donnell, J C Huffman J. Chem. Soc., Chem. Commun. 469 (1987)
147. A F Khlebnikov, M S Novikov, R R Kostikov Mendeleev Commun. 145 (1997)
148. W T Borden Chem. Commun. 1919 (1998)
149. M S Novikov, A F Khlebnikov, A E Masalev, R R Kostikov Tetrahedron Lett. 38 4187 (1997)
150. d
151. d
152. M S Novikov, A F Khlebnikov, M V Shevchenko J. Fluorine Chem. 123 177 (2003)
153. M S Novikov, A F Khlebnikov, O V Besedina, R R Kostikov Tetrahedron Lett. 42 533 (2001)
154. O Tsuge, U Kazunori Heterocycles 20 2133 (1983)
155. P N Confalone, E M Huie J. Am. Chem. Soc. 106 7175 (1984)
156. S Najdi, K-H Park, M M Olmstead, M J Kurth Tetrahedron Lett. 39 1685 (1998)
157. S Kanemasa, K Sakamoto, O Tsuge Bull. Chem. Soc. Jpn. 62 1960 (1989)
158. M S Novikov, A F Khlebnikov, E S Sidorina, R R Kostikov J. Fluorine Chem. 90 117 (1998)
159. M S Novikov, A F Khlebnikov, E S Sidorina, R R Kostikov J. Chem. Soc., Perkin Trans. 1 231 (2000)
160. M S Novikov, A F Khlebnikov, A Krebs, R R Kostikov Eur. J. Org. Chem. 133 (1998)
161. M S Novikov, I V Voznyi, A F Khlebnikov, Y Kopf, R R Kostikov J. Chem. Soc., Perkin Trans. 1 1628 (2002)
162. d
163. A F Khlebnikov, M S Novikov, A A Amer Tetrahedron Lett. 43 8523 (2002)