Carbonylation of heterocycles by homogeneous catalysts

Chemical Communications

Volumn , Issue 7, 2007, Pages 657-674

  Church, Tamara L ^a   Getzler, Yutan D Y L ^a,b   Byrne, Christopher M ^a   Coates, Geoffrey W ^a  

^a Department of Obstetrics Gynecology   (United States)

^b KENYON COLLEGE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AZIRIDINE; EPOXIDE; HETEROCYCLIC COMPOUND; LACTONE; OXAZOLINE DERIVATIVE;

ARTICLE; CARBONYLATION; CATALYSIS; CATALYST; CHEMICAL REACTION; PHYSICAL CHEMISTRY; POLYMERIZATION; RING OPENING;

EID: 33846938984     PISSN: 13597345     EISSN: None     Source Type: Journal    
DOI: 10.1039/b613476a     Document Type: Article

References (204)

1. J. P. Collman, L. S. Hegedus, J. R. Norton and R. G. Finke, Principles and Applications of Organotransition Metal Chemistry, University Science Books, Sausalito, CA, 1987
2. R. F. Heck, in Synthesis via Metal Carbonyls, ed., I. Wender, and, P. Pino,, New York, 1968
3. L. S. Hegedus, Transition Metals in the Synthesis of Complex Organic Molecules, University Science Books, Sausalito, CA, 1994
4. H. M. Colquhoun, D. J. Thompson and M. V. Twigg, Carbonylation: Direct Synthesis of Carbonyl Compounds, Plenum Press, New York, 1991
5. K. Khumtaveeporn H. Alper Acc. Chem. Res. 1995 28 414
6. J. Liu J. Chen Huaxue Jinzhan 2004 16 989
7. G. Vasapollo G. Mele Curr. Org. Chem. 2006 10 1397
8. G. Vasapollo G. Mele Targets Heterocycl. Systems 2002 6 197
9. R. F. Heck J. Am. Chem. Soc. 1963 85 1460
10. W. Reppe H. Kröper H. J. Pistor O. Weissbarth Justus Liebigs Ann. Chem. 1953 582 87
11. J. L. Eisenmann R. L. Yamartino J. F. Howard, Jr. J. Org. Chem. 1961 26 2102
12. S. Murahashi S. Horiie J. Am. Chem. Soc. 1956 78 4816
13. E. Drent and E. Kragtwijk (Shell Internationale Research Maatschappij B.V., Netherlands), Eur. Pat. Appl., EP 577206 (Chem. Abstr., 1994, 120, 191517c)
14. Y. D. Y. L. Getzler V. Mahadevan E. B. Lobkovsky G. W. Coates J. Am. Chem. Soc. 2002 124 1174
15. M. Allmendinger R. Eberhardt G. Luinstra B. Rieger J. Am. Chem. Soc. 2002 124 5646
16. J. T. Lee P. J. Thomas H. Alper J. Org. Chem. 2001 66 5424
17. K. D. Allen, T. G. James, J. F. Knifton, J. B. Powell, L. H. Slaugh and P. R. Weider (Shell Internationale Research Maatschappij B.V., Netherlands), PCT Int. Appl., WO 098887 (Chem. Abstr., 2002, 138, 14854)
18. K. Nakano M. Katayama S. Ishihara T. Hiyama K. Nozaki Synlett 2004 8 1367
19. R. Weber W. Keim M. Möthrath U. Englert B. Ganter Chem. Commun. 2000 1419
20. A. Rosenthal G. Kan Tetrahedron Lett. 1967 5 477
21. L. Roos R. W. Goetz M. Orchin J. Org. Chem. 1965 30 3023
22. Y. Takegami C. Yokokawa Y. Watanabe Bull. Chem. Soc. Jpn. 1964 37 935
23. C. Yokokawa Y. Watanabe Y. Takegami Bull. Chem. Soc. Jpn. 1964 37 677
24. C. J. Sullivan, in Ullman's Encyclopedia of Industrial Chemistry, ed., B. Elvers,,, S. Hawkins,,, W. Russey, and, G. Schulz,, New York, 1993
25. G. C. Komplin, J. B. Powell and P. R. Weider, 229th ACS National Meeting, San Diego, CA, 2005
26. T. C. Forschner and L. H. Slaugh (Shell Internationale Research Maatschappij B.V., Netherlands), PCT Int. Appl., WO 9940057 (Chem. Abstr., 1999, 131, 130385)
27. M. E. Piotti H. Alper J. Org. Chem. 1997 62 8484
28. J. G. Knight S. W. Ainge C. A. Baxter T. P. Eastman S. J. Harwood J. Chem. Soc., Perkin Trans. 1 2000 3188
29. H. Samain J. F. Carpentier A. Mortreux F. Petit New J. Chem. 1991 15 367
30. J. D. McClure J. Org. Chem. 1967 32 3888
31. K. Hinterding E. N. Jacobsen J. Org. Chem. 1999 64 2164
32. Though the structure of the branched product in methoxycarbonylation was not explicitly stated, we assume it to be the α-R-β-hydroxyester
33. Jacobsen notes that there is racemization when, in related chemistry, ring opening occurs to yield branched products. It seems possible that this would occur in methoxycarbonylation as well, or that inversion is a possibility, but neither question is directly addressed
34. A. Balázs C. Benedek G. Szalontai S. Törös Steroids 2004 69 271
35. J. Liu J. Chen C. Xia J. Mol. Catal. A: Chem. 2006 250 232
36. H. S. Kim J. Y. Bae J. S. Lee C. I. Jeong D. K. Choi S. O. Kang M. Cheong Appl. Catal. A: Gen. 2006 301 75
37. S. N. Goodman E. N. Jacobsen Angew. Chem., Int. Ed. 2002 41 4703
38. Y. Watanabe K. Nishiyama K. Zhang F. Okuda T. Kondo Y. Tsuji Bull. Chem. Soc. Jpn. 1994 67 879
39. Y. Fukumoto S. Yamaguchi N. Chatani S. Murai J. Organomet. Chem. 1995 489 215
40. J. Garapon, R. Touet and B. Sillion (Institut Francais du Petrole, Fr.), Fr. Pat., FR 2531077 (Chem. Abstr., 1984, 100, 192275)
41. J. Furukawa Y. Iseda T. Saegusa H. Fujii Makromol. Chem. 1965 89 263
42. H.-M. Müller D. Seebach Angew. Chem., Int. Ed. Engl. 1993 32 477
43. D. Takeuchi Y. Sakaguchi K. Osakada J. Polym. Sci. Part. A: Polym. Chem. 2002 40 4530
44. M. Allmendinger F. Molnar M. Zintl G. A. Luinstra P. Preishuber- Pflügl B. Rieger Chem. Eur. J. 2005 11 5327
45. M. Allmendinger M. Zintl R. Eberhardt G. A. Luinstra F. Molnar B. Rieger J. Organomet. Chem. 2004 689 971
46. M. Allmendinger R. Eberhardt G. A. Luinstra B. Rieger Macromol. Chem. Phys. 2003 204 564
47. M. Allmendinger R. Eberhardt G. A. Luinstra F. Molnar B. Rieger Z. Anorg. Allg. Chem. 2003 629 1347
48. M. Allmendinger R. Eberhardt G. Luinstra B. Rieger Polym. Mater.; Sci. Eng. 2002 87 223
49. M. Allmendinger R. Eberhardt G. Luinstra B. Rieger Polym. Mater.: Sci. Eng. 2002 87 89
50. G. Luinstra, F. Molnar, B. Rieger and M. Allmendinger (BASF AG, Germany), PCT Pat., WO A1 012860 (Chem. Abstr., 2004, 140, 163694)
51. M. Zintl, A. K. Hearley and B. Rieger, in Leading Edge Organometallic Chemistry Research, ed., M. A. Cato,, Nova Science Publishers, Inc., New York, 2006
52. J. T. Lee H. Alper Macromolecules 2004 37 2417
53. L. Jia E. Ding W. R. Anderson Chem. Commun. 2001 1436
54. L. Jia H. Sun J. T. Shay A. M. Allgeier S. D. Hanton J. Am. Chem. Soc. 2002 124 7282
55. J. Zhao E. Ding A. M. Allgeier L. Jia J. Polym. Sci. Part A: Polym. Chem. 2003 41 376
56. D. J. Darensbourg A. L. Phelps N. Le Gall L. Jia J. Am. Chem. Soc. 2004 126 13808
57. G. Liu L. Jia J. Am. Chem. Soc. 2004 126 14716
58. G. Liu L. Jia Angew. Chem., Int. Ed. 2006 45 129
59. A. K. Yudin, Aziridines and Epoxides in Organic Synthesis, Wiley-VCH Verlag GmbH & Co., Darmstadt, Germany, 2006
60. Q.-H. Xia H.-Q. Ge C.-P. Ye Z.-M. Liu K.-X. Su Chem. Rev. 2005 105 1603
61. J. F. Larrow E. N. Jacobsen Top. Organomet. Chem. 2004 6 123
62. Y. Wang R. L. Tennyson D. Romo Heterocycles 2004 64 605
63. C. Schneider Angew. Chem., Int. Ed. 2002 41 744
64. A. Pommier J.-M. Pons Synthesis 1993 441
65. P. Stutte, in Chirality in Industry, ed., A. N. Collins, G. N. Sheldrake and J. Crosby,, John Wiley & Sons, New York, 1992
66. Z. Liu A. S. Wasmuth S. G. Nelson J. Am. Chem. Soc. 2006 128 10352
67. X. Shen A. S. Wasmuth J. Zhao C. Zhu S. G. Nelson J. Am. Chem. Soc. 2006 128 7438
68. N. Fukuda K. Sasaki T. V. R. S. Sastry M. Kanai M. Shibasaki J. Org. Chem. 2006 71 1220
69. M. Shindo T. Yoshikawa Y. Itou S. Mori T. Nishii K. Shishido Chem. Eur. J. 2006 12 524
70. B. M. Trost J. P. N. Papillon T. Nussbaumer J. Am. Chem. Soc. 2005 127 17921
71. A. Pommier J.-M. Pons Synthesis 1995 729
72. C. Lowe J. C. Vederas Org. Prep. Proced. Int. 1995 27 305
73. E. P. Balskus E. N. Jacobsen J. Am. Chem. Soc. 2006 128 6810
74. G. Kumaraswamy M. Padmaja B. Markondaiah N. Jena B. Sridhar M. U. Kiran J. Org. Chem. 2006 71 337
75. P. G. Williams G. O. Buchanan R. H. Feling C. A. Kauffman P. R. Jensen W. Fenical J. Org. Chem. 2005 70 6196
76. R. R. Manam S. Teisan D. J. White B. Nicholson J. Grodberg S. T. C. Neuteboom K. S. Lam D. A. Mosca G. K. Lloyd B. C. M. Potts J. Nat. Prod. 2005 68 240
77. B. D. Morris R. R. Smyth S. P. Foster M. P. Hoffmann W. L. Roelofs S. Francke W. Francke J. Nat. Prod. 2005 68 26
78. S. C. Archibald D. J. Barden J. F. Y. Bazin I. Fleming C. F. Foster A. K. Mandal A. K. Mandal D. Parker K. Takaki A. C. Ware A. R. B. Williams A. B. Zwicky Org. Biomol. Chem. 2004 2 1051
79. M. S. Lall C. Karvellas J. C. Vederas Org. Lett. 1999 1 803
80. T. J. Schmidt E. Okuyama F. R. Fronczek Bioorg. Med. Chem. 1999 7 2857
81. J. Wu T.-L. Yu C.-T. Chen C.-C. Lin Coord. Chem. Rev. 2006 250 602
82. K. Sudesh H. Abe Y. Doi Prog. Polym. Sci. 2000 25 1503
83. O. Coulembier L. Mespouille J. L. Hedrick R. M. Waymouth P. Dubois Macromolecules 2006 39 4001
84. A. Amgoune C. M. Thomas S. Ilinca T. Roisnel J.-F. Carpentier Angew. Chem., Int. Ed. 2006 45 2782
85. L. R. Rieth D. R. Moore E. B. Lobkovsky G. W. Coates J. Am. Chem. Soc. 2002 124 15239
86. E. F. Connor G. W. Nyce M. Myers A. Möck J. L. Hedrick J. Am. Chem. Soc. 2002 124 914
87. H. W. Yang D. Romo Tetrahedron 1999 55 6403
88. R. K. Orr M. A. Calter Tetrahedron 2003 59 3545
89. H. Wynberg Top. Stereochem. 1986 16 87
90. M. A. Calter O. A. Tretyak C. Flaschenreim Org. Lett. 2005 7 1809
91. J. E. Wilson G. C. Fu Angew. Chem., Int. Ed. 2004 43 6358
92. C. Zhu X. Shen S. G. Nelson J. Am. Chem. Soc. 2004 126 5352
93. S. G. Nelson C. Zhu X. Shen J. Am. Chem. Soc. 2004 126 14
94. D. A. Evans J. M. Janey Org. Lett. 2001 3 2125
95. Y. Kamiya K. Kawato H. Ohta Chem. Lett. 1980 9 1549
96. I. Shimizu T. Maruyama T. Makuta A. Yamamoto Tetrahedron Lett. 1993 34 2135
97. R. Aumann H. Ring Angew. Chem., Int. Ed. Engl. 1977 16 50
98. F. Molnar G. A. Luinstra M. Allmendinger B. Rieger Chem. Eur. J. 2003 9 1273
99. A. Sacco Atti. Accad. Nazl. Lincei: Rend. Sc. Fis. Mat. Nat. 1956 21 442
100. W. Hieber W. Freyer Chem. Ber. 1958 91 1230
101. J. W. Kramer E. B. Lobkovsky G. W. Coates Org. Lett. 2006 8 3709
102. J. A. R. Schmidt E. B. Lobkovsky G. W. Coates J. Am. Chem. Soc. 2005 127 11426
103. J. A. R. Schmidt V. Mahadevan Y. D. Y. L. Getzler G. W. Coates Org. Lett. 2004 6 373
104. Y. D. Y. L. Getzler V. Mahadevan E. B. Lobkovsky G. W. Coates Pure Appl. Chem. 2004 76 557
105. G. W. Coates, Y. D. Y. L. Getzler, P. Wolczanski and V. Mahadevan (Cornell Research Foundation, Inc., US), PCT Pat., WO 050154 A2 (Chem. Abstr., 2003, 139, 54560)
106. G. W. Coates, Y. D. Y. L. Getzler, P. Wolczanski and V. Mahadevan (Cornell Research Foundation, Inc., US), US Pat., US 0162961 A1 (Chem. Abstr., 2003, 139, 54560)
107. J. M. Rowley E. B. Lobkovsky G. W. Coates J. Am. Chem. Soc.
108. Though many catalyst systems are described as 'well-defined', the term itself remains rather ill-defined. Herein we proffer that a well-defined catalyst is a discrete metal complex or organic compound with either a known structure or exact molecular stoichiometry (or both) that, with minimal chemical or physical change, acts as the active catalytic species for a given transformation. Typically, such a metal complex features a permanent ligand set, and operates by a reproducible mechanism in which the active species is regenerated after each catalytic cycle
109. J. S. Merola K. S. Campo R. A. Gentile Inorg. Chem. 1989 28 2950
110. V. Mahadevan Y. D. Y. L. Getzler G. W. Coates Angew. Chem., Int. Ed. 2002 41 2781
111. M. E. Piotti H. Alper J. Am. Chem. Soc. 1996 118 111
112. P. Davoli I. Moretti F. Prati H. Alper J. Org. Chem. 1999 64 518
113. Though the product β-lactone was found to be enantioenriched by chiral gas chromatography, the absolute configuration of the major stereoisomer was not determined
114. J. L. Eisenmann J. Org. Chem. 1962 27 2706
115. J. Prandi J. L. Namy G. Menoret H. B. Kagan J. Organomet. Chem. 1985 285 449
116. T. W. Greene and P. G. M. Wuts, Protective Groups in Organic Synthesis, John Wiley & Sons, Inc., New York, 1991
117. M. B. Smith and J. March, March's Advanced Organic Chemistry, John Wiley & Sons, Inc., New York, 2001
118. Y. Fukumoto N. Chatani S. Murai J. Org. Chem. 1993 58 4187
119. T. Murai E. Yasui S. Kato Y. Hatayama S. Suzuki Y. Yamasaki N. Sonoda H. Kurosawa Y. Kawasaki S. Murai J. Am. Chem. Soc. 1989 111 7938
120. T. Murai S. Kato S. Murai T. Toki S. Suzuki N. Sonoda J. Am. Chem. Soc. 1984 106 6093
121. T. Brima, (National Distillers and Chemical Corp., USA), US Pat., US 4968817 (Chem. Abstr., 1990, 114, 185246)
122. Y. D. Y. L. Getzler, PhD Dissertation, Cornell University, Ithaca, NY, 2004
123. S. Winstein R. E. Buckles J. Am. Chem. Soc. 1942 64 2780
124. W. G. Overend, in The Carbohydrates: Chemistry and Biochemistry, ed., W. Pigman, and, D. Horton,, Academic Press, New York, 1972
125. T. L. Church Y. D. Y. L. Getzler G. W. Coates J. Am. Chem. Soc. 2006 128 10125
126. A. Stirling M. Iannuzzi M. Parrinello F. Molnar V. Bernhart G. A. Luinstra Organometallics 2005 24 2533
127. M. Gasperini F. Ragaini Organometallics 2004 23 995
128. T. Sekiguchi S. Maki H. Niwa H. Ikeda T. Hirano Tetrahedron Lett. 2004 45 1065
129. S. Fukuzumi K. Ohkubo Chem. Eur. J. 2000 6 4532
130. K. Ohkubo S. C. Menon A. Orita J. Otera S. Fukuzumi J. Org. Chem. 2003 68 4720
131. K. Ohkubo T. Suenobu H. Imahori A. Orita J. Otera S. Fukuzumi Chem. Lett. 2001 30 978
132. H. Ohtsu S. Fukuzumi Chem. Lett. 2001 30 920
133. P. C. Ford S. Massick Coord. Chem. Rev. 2002 226 39
134. I. Kovács F. Ungváry Coord. Chem. Rev. 1997 161 1
135. V. Galamb G. Pályi Coord. Chem. Rev. 1984 59 203
136. F. Ungváry L. Markó Inorg. Chim. Acta 1994 227 211
137. R. L. Sweany Organometallics 1989 8 175
138. L. Verslius T. Ziegler E. J. Baerends W. Ravenek J. Am. Chem. Soc. 1989 111 2018
139. D. C. Roe Organometallics 1987 6 942
140. R. F. Heck D. S. Breslow J. Am. Chem. Soc. 1961 83 4023
141. T. L. Church, C. M. Byrne, E. B. Lobkovsky and G. W. Coates, manuscript in preparation
142. N. Choi W. Ando Organometallics 1994 13 741
143. K. C. Brinkman J. A. Gladysz J. Chem. Soc., Chem. Commun. 1980 1260
144. P. T. Matsunaga G. L. Hillhouse Angew. Chem., Int. Ed. Engl. 1994 33 1748
145. R. D. Adams J. A. Belinski J. H. Yamamoto Organometallics 1992 11 3422
146. H. J. Nienburg and G. Elschnigg (Badische Anilin- & Soda-Fabrik Akt.-Ges.), Ger. Pat., DE 1066572 (Chem. Abstr., 1959, 55, 53975)
147. M.-D. Wang S. Calet H. Alper J. Org. Chem. 1989 54 20
148. Y. D. Y. L. Getzler V. Kundnani E. B. Lobkovsky G. W. Coates J. Am. Chem. Soc. 2004 126 6842
149. M. Furuya S. Tsutsuminai H. Nagasawa N. Komine M. Hirano S. Komiya Chem. Commun. 2003 2046
150. K. M. Arason S. C. Bergmeier Org. Prep. Proced. Int. 2002 34 337
151. C. Fumagalli, in Kirk-Othmer Encyclopedia of Chemical Technology, ed., J. I. Kroschwitz, and, M. Howe-Grant,, John Wiley & Sons, New York, 1997
152. Y. Mori J. Tsuji Bull. Chem. Soc. Jpn. 1969 42 777
153. G. Bitsi H. Kheradmand G. Jenner J. Organomet. Chem. 1986 310 115
154. (S)-Methylsuccinic anhydride was produced with 99% ee when the carbonylation was performed at 55°C. At 80°C, some product racemization occurred
155. H. Alper H. Arzoumanian J.-F. Petrignani M. Saldana-Maldonado J. Chem. Soc., Chem. Commun. 1985 340
156. H. Alper A. Eisenstat N. Satyanarayana J. Am. Chem. Soc. 1990 112 7060
157. The Organic Chemistry of β-Lactams, ed., G. I. Georg,, VCH Publishers, Inc., New York, 1993
158. C. Palomo J. M. Aizpurua I. Ganboa M. Oiarbide Eur. J. Org. Chem. 1999 3223
159. M. Benaglia M. Cinquini F. Cozzi Eur. J. Org. Chem. 2000 563
160. S. France A. Weatherwax A. E. Taggi T. Lectka Acc. Chem. Res. 2004 37 592
161. A. E. Taggi A. A. Hafez T. Lectka Acc. Chem. Res. 2003 36 10
162. M. Avalos R. Babiano P. Cintas J. L. Jimenez J. C. Palacios Acc. Chem. Res. 2005 38 460
163. P. Davoli F. Prati Heterocycles 2000 53 2379
164. P. Davoli A. Forni I. Moretti F. Prati G. Torre Tetrahedron 2001 57 1801
165. S.-M. Lu H. Alper J. Org. Chem. 2004 69 3558
166. P. Davoli A. Spaggiari A. Ciamaroni A. Forni G. Torre F. Prati Heterocycles 2004 63 2495
167. H. Alper F. Urso D. J. H. Smith J. Am. Chem. Soc. 1983 105 6737
168. S. Calet F. Urso H. Alper J. Am. Chem. Soc. 1989 111 931
169. D. Ardura R. López T. Sordo J. Org. Chem. 2006 71 7315
170. H. E. Bryndza W. C. Fultz W. Tam Organometallics 1985 4 939
171. D. Nathwani M. J. Wood Drugs 1993 45 866
172. B. Alcaide P. Almendros Curr. Org. Chem. 2002 6 245
173. J. R. Hwu K. S. Ethiraj G. H. Hakimelahi Mini-Rev. Med. Chem. 2003 3 305
174. V. K. Aggarwal E. Alonso M. Ferrara S. E. Spey J. Org. Chem. 2002 67 2335
175. This represents an enantiomeric excess of 99%, assuming that the l-menthol additive was 100% enantiopure
176. S.-M. Lu H. Alper J. Am. Chem. Soc. 2003 125 13126
177. S.-M. Lu H. Alper J. Am. Chem. Soc. 2005 127 14776
178. M. Kidwai P. Sapra K. R. Bhushan Curr. Med. Chem. 1999 6 195
179. C. J. Schofield M. W. Walter Amino Acids, Peptides Proteins 1999 30 335
180. M. I. Konaklieva Curr. Med. Chem.: Anti-Infect. Agents 2002 1 215
181. A. G. Brown Pure Appl. Chem. 1987 59 475
182. I. Ojima Adv. Asymmetric Synth. 1995 1 95
183. C. Palomo J. M. Aizpurua I. Ganboa M. Oiarbide Amino Acids 1999 16 321
184. B. Alcaide P. Almendros Synlett 2002 3 381
185. B. Alcaide P. Almendros Curr. Med. Chem. 2004 11 1921
186. K. Hashimoto K. Hotta M. Okada S. Nagata J. Polym. Sci., Part A: Polym. Chem. 1995 33 1995
187. K. Hashimoto T. Oi J. Yasuda K. Hotta M. Okada J. Polym. Sci., Part A: Polym. Chem. 1997 35 1831
188. K. Hashimoto J. Yasuda M. Kobayashi J. Polym. Sci., Part A: Polym. Chem. 1999 37 909
189. J. Cheng T. J. Deming J. Am. Chem. Soc. 2001 123 9457
190. W. Chamchaang A. R. Pinhas J. Chem. Soc., Chem. Commun. 1988 710
191. W. H. Leung W. L. Mak E. Y. Y. Chan T. C. H. Lam W. S. Lee H. L. Kwong L. L. Yeung Synlett 2002 1688
192. H. Osborn J. Sweeney Tetrahedron: Asymmetry 1997 8 1693
193. D. Tanner Angew. Chem., Int. Ed. Engl. 1994 33 599
194. H. Alper C. P. Mahatantila Heterocycles 1983 20 2025
195. H. Alper C. P. Perera F. R. Ahmed J. Am. Chem. Soc. 1981 103 1289
196. D. Roberto H. Alper Organometallics 1984 3 1767
197. H. Alper D. Delledonne M. Kameyama D. Roberto Organometallics 1990 9 762
198. D. Roberto H. Alper J. Am. Chem. Soc. 1989 111 7539
199. M. Komatsu S. Tamabuchi S. Minakata Y. Ohshiro Heterocycles 1999 50 67
200. B. G. Van den Hoven H. Alper J. Am. Chem. Soc. 2001 123 1017
201. K. Okuro T. Dang K. Khumtaveeporn H. Alper Tetrahedron Lett. 1996 37 2713
202. G. Jenner H. Kheradmand A. Kiennemann J. Organomet. Chem. 1984 277 427
203. H. Xu L. Jia Org. Lett. 2003 5 1575
204. H. Xu J. A. Gladding L. Jia Inorg. Chim. Acta 2004 357 4024