In search of an atom-economical synthesis of chiral ynamides

Synlett

Volumn , Issue 10, 2003, Pages 1379-1390

  Mulder, Jason A ^a   Kurtz, Kimberly C M ^a   Hsung, Richard P ^a  

^a University of Minnesota   (United States)

Author keywords

Alkynyl halides; Base promoted isomerization of propargyl amides; Copper catalyzed cross couplings of amides; Electron deficient ynamines; Ynamides; Ynamines

Indexed keywords

ALKYNYL GROUP; AMIDE; COPPER; HALOGEN; IODINE DERIVATIVE; LITHIUM; PALLADIUM;

ATOM; CATALYSIS; CHEMISTRY; CHIRALITY; ELECTRON; ISOMERISM; REVIEW; SYNTHESIS;

EID: 0042069896     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2003-40817     Document Type: Review

References (142)

1. For the first report see: (a) Bode, J. Annals 1892, 267, 268. (b) Bode, J. Annals 1892, 267, 286. (c) For a correction of this claim see: Klages, F.; Drerup, E. Annals 1941, 547, 65.
2. For the first report see: (a) Bode, J. Annals 1892, 267, 268. (b) Bode, J. Annals 1892, 267, 286. (c) For a correction of this claim see: Klages, F.; Drerup, E. Annals 1941, 547, 65.
3. For the first report see: (a) Bode, J. Annals 1892, 267, 268. (b) Bode, J. Annals 1892, 267, 286. (c) For a correction of this claim see: Klages, F.; Drerup, E. Annals 1941, 547, 65.
4. (a) Viehe, H. G. Angew Chem., Int. Ed. Engl. 1963, 2, 477.
5. (b) Wolf, V.; Kowitz, F. Annals 1960, 638, 33.
6. (c) Zaugg, H. E.; Swett, L. R.; Stone, G. R. J. Org. Chem. 1958, 23, 1389.
7. (a) Viehe, H. G. Angew Chem., Int. Ed. Engl. 1967, 6, 767.
8. (b) Viehe, H. G. Chemistry of Acetylenes; Marcel Dekker: New York, 1969, Chap. 12, 861-912.
9. Ficini, J. Tetrahedron 1976, 32, 1448.
10. (a) Pitacco, G.; Valentin, E. Enamines and Ynamines In Chemistry of Functional Groups; Wiley: Chichester, 1979, Chap. 15, 623-714.
11. (b) Collard-Motte, J.; Janousek, Z. Top. Curr. Chem. 1985, 130, 89.
12. For ynol ethers: Stang, P. J.; Zhdankin, V. V. Ynol Ethers and Esters in the Chemistry of Triple-Bonded Functional Groups, Supplement C2 Vol. 2; Patai, S., Ed.; John Wiley & Sons Ltd.: Chichester, 1994, Chap. 19, 1135-1164.
13. Himbert, G. In Houben-Weyl, Methoden der Organischen Chemie; Kropf, H.; Schaumann, E., Eds.; Georg Thieme Verlag: Stuttgart, 1993, 3267-3443.
14. Hsung, R. P.; Zificsak, C. A.; Mulder, J. A.; Rameshkumar, C.; Wei, L.-L. Tetrahedron 2001, 57, 7575.
15. The unfortunate and premature loss of Professor J. Ficini is one critical reason for lack of advancement in the field.
16. No real attempt is being made in this account to truly distinguish or classify various different electron deficient ynamines 1-9 in Figure 2, however, for certain level of structural clarity and convenience we have regarded compounds 1-5 as electron deficient ynamines whereas compounds 6-9 in which the nitrogen atom is directly attached to an electron-withdrawing carbonyl or sulfonyl group as ynamides.
17. (a) Janousek, Z.; Collard, J.; Viehe, H. G. Angew. Chem., Int. Ed. Engl. 1972, 11, 917.
18. (b) Goffin, E.; Legrand, Y.; Viehe, H. G. J. Chem. Res., Synop. 1977, 105.
19. Schottelius, M. J.; Chen, P. Helv. Chim. Acta 1998, 81, 2341.
20. (a) Rainier, J. D.; Imbriglio, J. E. J. Org. Chem. 2000, 65, 7272.
21. (b) Rainier, J. D.; Imbriglio, J. E. Org. Lett. 1999, 1, 2037.
22. (a) Witulski, B.; Stengel, T. Angew. Chem. Int. Ed. 1998, 37, 489.
23. (b) Witulski, B.; Gößmann, M. Synlett 2000, 1793.
24. For intramolecular [2+2+1] cycloaddition see: Witulski, B.; Gößmann, M. Chem. Commun. 1999, 1879.
25. (a) Witulski, B.; Stengel, T. Angew. Chem. Int. Ed. 1998, 38, 2426.
26. (b) Witulski, B.; Stengel, T.; Fernàndez-Hernàndez, J. M. Chem. Commun. 2000, 1965.
27. (c) Witulski, B.; Alayrac, C. Angew. Chem. Int. Ed. 2002, 41, 3281.
28. Witulski, B.; Buschmann, N.; Bergsträßer, U. Tetrahedron 2000, 56, 8473.
29. Hoffmann, R. W.; Brückner, D. New J. Chem. 2001, 25, 369.
30. Saito, N.; Sato, Y.; Mori, M. Org. Lett. 2002, 4, 803.
31. Huang, J.; Xiong, H.; Hsung, R. P.; Rameshkumar, C.; Mulder, J. A.; Grebe, T. P. Org. Lett. 2002, 4, 2417.
32. Mulder, J. A.; Hsung, R. P.; Frederick, M. O.; Tracey, M. R.; Zificsak, C. A. Org. Lett. 2002, 4, 1383.
33. Hsung, R. P.; Zificsak, C.; Wei, L.-L.; Douglas, C. J.; Xiong, H.; Mulder, J. Org. Lett. 1999, 1, 1237.
34. Witulski, B.; Lumtscher, J.; Bergsträßer, U. Synlett 2003, 708.
35. (a) Minière, S.; Cintrat, J.-C. Synthesis 2001, 705.
36. (b) Minière, S.; Cintrat, J.-C. J. Org. Chem. 2001, 66, 7385.
37. (c) Timbert, J.-C.; Cintrat, J.-C. Chem.-Eur. J. 2002, 8, 1637.
38. (d) Personal communication with Professor J.-C. Cintrat. Their manuscript has been submitted.
39. Tanaka, R.; Hirano, S.; Urabe, H.; Sato, F. Org. Lett. 2003, 5, 67.
40. The only account using chiral ynamines before 1997, see: (a) van Elburg, P. A.; Honig, G. W. N.; Reinhoudt, D. N. Tetrahedron Lett. 1987, 28, 6397. (b) For the recent two accounts of chemistry of chiral ynamines see: Balsells, J.; Vázquez, J.; Moyano, A.; Pericàs, M. A.; Riera, A. J. Org. Chem. 2000, 65, 7291. (c) See also: Roth, G.; Reindl, D.; Gockel, M.; Troll, C.; Fischer, H. Organometallics 1998, 17, 1393. (d) Fischer, H.; Podschadly, O.; Roth, G.; Herminghaus, S.; Klewitz, S.; Heck, J.; Houbrechts, S.; Meyer, T. J. Organomet. Chem. 1997, 541, 321.
41. The only account using chiral ynamines before 1997, see: (a) van Elburg, P. A.; Honig, G. W. N.; Reinhoudt, D. N. Tetrahedron Lett. 1987, 28, 6397. (b) For the recent two accounts of chemistry of chiral ynamines see: Balsells, J.; Vázquez, J.; Moyano, A.; Pericàs, M. A.; Riera, A. J. Org. Chem. 2000, 65, 7291. (c) See also: Roth, G.; Reindl, D.; Gockel, M.; Troll, C.; Fischer, H. Organometallics 1998, 17, 1393. (d) Fischer, H.; Podschadly, O.; Roth, G.; Herminghaus, S.; Klewitz, S.; Heck, J.; Houbrechts, S.; Meyer, T. J. Organomet. Chem. 1997, 541, 321.
42. The only account using chiral ynamines before 1997, see: (a) van Elburg, P. A.; Honig, G. W. N.; Reinhoudt, D. N. Tetrahedron Lett. 1987, 28, 6397. (b) For the recent two accounts of chemistry of chiral ynamines see: Balsells, J.; Vázquez, J.; Moyano, A.; Pericàs, M. A.; Riera, A. J. Org. Chem. 2000, 65, 7291. (c) See also: Roth, G.; Reindl, D.; Gockel, M.; Troll, C.; Fischer, H. Organometallics 1998, 17, 1393. (d) Fischer, H.; Podschadly, O.; Roth, G.; Herminghaus, S.; Klewitz, S.; Heck, J.; Houbrechts, S.; Meyer, T. J. Organomet. Chem. 1997, 541, 321.
43. The only account using chiral ynamines before 1997, see: (a) van Elburg, P. A.; Honig, G. W. N.; Reinhoudt, D. N. Tetrahedron Lett. 1987, 28, 6397. (b) For the recent two accounts of chemistry of chiral ynamines see: Balsells, J.; Vázquez, J.; Moyano, A.; Pericàs, M. A.; Riera, A. J. Org. Chem. 2000, 65, 7291. (c) See also: Roth, G.; Reindl, D.; Gockel, M.; Troll, C.; Fischer, H. Organometallics 1998, 17, 1393. (d) Fischer, H.; Podschadly, O.; Roth, G.; Herminghaus, S.; Klewitz, S.; Heck, J.; Houbrechts, S.; Meyer, T. J. Organomet. Chem. 1997, 541, 321.
44. For the only intramolecular reaction using ynamine see: Genet, J. P.; Kahn, P.; Ficini, J. Tetrahedron Lett. 1980, 21, 1521.
45. For reviews on palladium catalyzed N-arylations of amines and amides see: (a) Hartwig, J. F. Angew. Chem. Int. Ed. 1998, 37, 2046. (b) Wolfe, J. P.; Wagaw, S.; Marcoux, J.-F.; Buchwald, S. L. Acc. Chem. Res. 1998, 31, 805. (c) For an earlier account see: Kosugi, M.; Kameyama, M.; Migita, T. Chem. Lett. 1983, 927.
46. For reviews on palladium catalyzed N-arylations of amines and amides see: (a) Hartwig, J. F. Angew. Chem. Int. Ed. 1998, 37, 2046. (b) Wolfe, J. P.; Wagaw, S.; Marcoux, J.-F.; Buchwald, S. L. Acc. Chem. Res. 1998, 31, 805. (c) For an earlier account see: Kosugi, M.; Kameyama, M.; Migita, T. Chem. Lett. 1983, 927.
47. For reviews on palladium catalyzed N-arylations of amines and amides see: (a) Hartwig, J. F. Angew. Chem. Int. Ed. 1998, 37, 2046. (b) Wolfe, J. P.; Wagaw, S.; Marcoux, J.-F.; Buchwald, S. L. Acc. Chem. Res. 1998, 31, 805. (c) For an earlier account see: Kosugi, M.; Kameyama, M.; Migita, T. Chem. Lett. 1983, 927.
48. From Buchwald's lab see: (a) Wolfe, J. P.; Tomori, H.; Sadighi, J. P.; Yin, J.; Buchwald, S. L. J. Org. Chem. 2000, 65, 1158; and references therein. (b) Yin, J.; Buchwald, S. L. Org. Lett. 2000, 2, 1101. (c) Yin, J.; Buchwald, S. L. J. Am. Chem. Soc. 2002, 124, 6043.
49. From Buchwald's lab see: (a) Wolfe, J. P.; Tomori, H.; Sadighi, J. P.; Yin, J.; Buchwald, S. L. J. Org. Chem. 2000, 65, 1158; and references therein. (b) Yin, J.; Buchwald, S. L. Org. Lett. 2000, 2, 1101. (c) Yin, J.; Buchwald, S. L. J. Am. Chem. Soc. 2002, 124, 6043.
50. From Buchwald's lab see: (a) Wolfe, J. P.; Tomori, H.; Sadighi, J. P.; Yin, J.; Buchwald, S. L. J. Org. Chem. 2000, 65, 1158; and references therein. (b) Yin, J.; Buchwald, S. L. Org. Lett. 2000, 2, 1101. (c) Yin, J.; Buchwald, S. L. J. Am. Chem. Soc. 2002, 124, 6043.
51. From Hartwig's lab see: (a) Hamann, B. C.; Hartwig, J. F. J. Am. Chem. Soc. 1998, 120, 3694. (b) Mann, G.; Hartwig, J. F.; Driver, M. S.; Fernández-Rivas, C. J. Am. Chem. Soc. 1998, 120, 827. (c) Hartwig, J. F. ; Kawatsura, M.; Hauck, S. I.; Shaughnessy, K. H.; Alcazar-Roman, L. M. J. Org. Chem. 1999, 64, 5575.
52. From Hartwig's lab see: (a) Hamann, B. C.; Hartwig, J. F. J. Am. Chem. Soc. 1998, 120, 3694. (b) Mann, G.; Hartwig, J. F.; Driver, M. S.; Fernández-Rivas, C. J. Am. Chem. Soc. 1998, 120, 827. (c) Hartwig, J. F. ; Kawatsura, M.; Hauck, S. I.; Shaughnessy, K. H.; Alcazar-Roman, L. M. J. Org. Chem. 1999, 64, 5575.
53. From Hartwig's lab see: (a) Hamann, B. C.; Hartwig, J. F. J. Am. Chem. Soc. 1998, 120, 3694. (b) Mann, G.; Hartwig, J. F.; Driver, M. S.; Fernández-Rivas, C. J. Am. Chem. Soc. 1998, 120, 827. (c) Hartwig, J. F. ; Kawatsura, M.; Hauck, S. I.; Shaughnessy, K. H.; Alcazar-Roman, L. M. J. Org. Chem. 1999, 64, 5575.
54. Recent examples: (a) Cacchi, S.; Fabrizi, G.; Goggiamani, A.; Zappia, G. Org. Lett. 2001, 3, 2539. (b) Artamkina, G. A.; Sergeev, A. G.; Beletskaya, I. P. Tetrahedron Lett. 2001, 42, 4381. (c) Edmondson, S. D.; Mastracchio, A.; Parmee, E. R. Org. Lett. 2000, 2, 1109. (d) Bolm, C.; Hildebrand, J. J. Org. Chem. 2000, 65, 169.
55. Recent examples: (a) Cacchi, S.; Fabrizi, G.; Goggiamani, A.; Zappia, G. Org. Lett. 2001, 3, 2539. (b) Artamkina, G. A.; Sergeev, A. G.; Beletskaya, I. P. Tetrahedron Lett. 2001, 42, 4381. (c) Edmondson, S. D.; Mastracchio, A.; Parmee, E. R. Org. Lett. 2000, 2, 1109. (d) Bolm, C.; Hildebrand, J. J. Org. Chem. 2000, 65, 169.
56. Recent examples: (a) Cacchi, S.; Fabrizi, G.; Goggiamani, A.; Zappia, G. Org. Lett. 2001, 3, 2539. (b) Artamkina, G. A.; Sergeev, A. G.; Beletskaya, I. P. Tetrahedron Lett. 2001, 42, 4381. (c) Edmondson, S. D.; Mastracchio, A.; Parmee, E. R. Org. Lett. 2000, 2, 1109. (d) Bolm, C.; Hildebrand, J. J. Org. Chem. 2000, 65, 169.
57. Recent examples: (a) Cacchi, S.; Fabrizi, G.; Goggiamani, A.; Zappia, G. Org. Lett. 2001, 3, 2539. (b) Artamkina, G. A.; Sergeev, A. G.; Beletskaya, I. P. Tetrahedron Lett. 2001, 42, 4381. (c) Edmondson, S. D.; Mastracchio, A.; Parmee, E. R. Org. Lett. 2000, 2, 1109. (d) Bolm, C.; Hildebrand, J. J. Org. Chem. 2000, 65, 169.
58. (a) Murch, P.; Williamson, B. L.; Stang, P. J. Synthesis 1994, 1255.
59. (b) Zhdankin, V. V.; Stang, P. J. Tetrahedron 1998, 54, 10927.
60. (a) Kitamura, T.; Tashi, N.; Tsuda, K.; Fujiwara, Y. Tetrahedron Lett. 1998, 39, 3787.
61. (b) Kitamura, T.; Tashi, N.; Tsuda, K.; Chen, H.; Fujiwara, Y. Heterocycles 2000, 52, 303.
62. Feldman, K. S.; Bruendl, M. M.; Schildknegt, K.; Bohnstedt, A. C. J. Org. Chem. 1996, 61, 5440.
63. (a) Balsamo, A.; Macchia, B.; Macchia, F.; Rossello, A.; Domiano, P. Tetrahedron Lett. 1985, 26, 4141.
64. sp-N bond formation in synthesis of ynamines see: Petersen, L. I. Tetrahedron Lett. 1968, 9, 5357.
65. Zaugg, H. E.; Swett, L. R.; Stone, G. R. J. Org. Chem. 1958, 23, 1389.
66. (a) Galy, J. P.; Elguero, J.; Vincent, E. J.; Galy, A. M.; Barbe, J. Synthesis 1979, 944.
67. (b) Mahamoud, A.; Galy, J. P.; Vincent, E. J.; Barbe, J. Synthesis 1981, 917.
68. (c) Radl, S.; Kovarova, L.; Holubeck, J. Coll. Czech. Chem. Commun. 1991, 56, 439.
69. (d) Radl, S.; Kovarova, L. Coll. Czech. Chem. Commun. 1991, 56, 2413.
70. Katritzky, A. R.; Ramer, W. H. J. Org. Chem. 1985, 50, 852.
71. Majumdar, K. C.; Ghosh, S. K. Synth. Commun. 1994, 24, 217.
72. Wei, L.-L.; Xiong, H.; Douglas, C. J.; Hsung, R. P. Tetrahedron Lett. 1999, 40, 6903.
73. Wei, L.-L.; Mulder, J. A.; Xiong, H.; Zificsak, C. A.; Douglas, C. J.; Hsung, R. P. Tetrahedron 2001, 57, 459.
74. For a review see: Saalfrank, R. W.; Lurz, C. J. In Houben-Weyl, Methoden Der Organischen Chemie; Kropf, H.; Schaumann, E., Eds.; Georg Thieme Verlag: Stuttgart, 1993, 3093.
75. (a) Rameshkumar, C.; Xiong, H.; Tracey, M. R.; Berry, C. R.; Yao, L. J.; Hsung, R. P. J. Org. Chem. 2002, 67, 1339.
76. (b) Xiong, H.; Hsung, R. P.; Berry, C. R.; Rameshkumar, C. J. Am. Chem. Soc. 2001, 123, 7174.
77. (c) Xiong, H.; Hsung, R. P.; Wei, L.-L.; Berry, C. R.; Mulder, J. A.; Stockwell, B. Org. Lett. 2000, 2, 2869.
78. (d) Wei, L.-L.; Hsung, R. P.; Xiong, H.; Mulder, J. A.; Nkansah, N. T. Org. Lett. 1999, 1, 2145.
79. Joshi, R. V.; Xu, Z.-Q.; Ksebati, M. B.; Kessel, D.; Corbett, T. H.; Drach, J. C.; Zemlicka, J. J. Chem. Soc., Perkin Trans. 1 1994, 1089.
80. Brückner, D. Synlett 2000, 1402.
81. Bloxham, J.; Dell, C. P. J. Chem. Soc. Perkin Trans. 1 1993, 3055.
82. (a) Claisen, L. Ber. Dtsch. Chem. Ges. 1912, 45, 3157.
83. (b) For other major variations see: Carroll, M. F. J. Chem. Soc. 1940, 704.
84. (c) See also: Wick, A. E.; Felix, D.; Steen, K.; Eschenmoser, A. Helv. Chim. Acta 1964, 47, 2425.
85. (d) See also: Johnson, W. S.; Werthemann, L.; Bartlett, W. R.; Brocksom, T. J.; Li, T.-T.; Faulkner, D. J.; Petersen, M. R. J. Am. Chem. Soc. 1970, 92, 741.
86. (e) See also: Ireland, R. E.; Mueller, R. H. J. Am. Chem. Soc. 1972, 94, 5897.
87. (a) Wipf, P. In Comprehensive Organic Synthesis, Vol. 5; Trost, B. M.; Fleming, I., Eds.; Pergamon Press: Oxford, 1991, 827.
88. (b) Frauenrath, H. In Houben-Weyl, Methoden Der Organischen Chemie; Kropf, H.; Schaumann, E., Eds.; Georg Thieme Verlag: Stuttgart, 1995, 3301.
89. (c) Hill, R. K. In Asymmetric Synthesis; Morrison, J. D., Ed.; Academic Press: New York, 1984.
90. (d) Gajewski, J. J. Hydrocarbon Thermal Isomerizations; Academic Press: New York, 1981.
91. Also see: (a) Ito, H.; Taguchi, T. Chem. Soc. Rev. 1999, 28, 43. (b) Enders, D.; Knopp, M.; Schiffers, R. Tetrahedron: Asymmetry 1996, 7, 1847. (c) Blechert, S. Synthesis 1989, 71. (d) Kallmerten, J.; Wittman, M. D. Stud. Nat. Prod. Chem. 1989, 3, 233. (e) Ziegler, F. E. Chem. Rev. 1988, 88, 1423. (f) Murray, A. W. Org. React. Mech. 1987, 457. (g) Murray, A. W. Org. React. Mech. 1986, 429. (h) Moody, C. J. Adv. Heterocycl. Chem. 1987, 42, 203. (i) Barlett, P. A. Tetrahedron 1980, 36, 3. (j) Lutz, R. P. Chem. Rev. 1984, 84, 205. (k) Rhoads, S. J.; Raulins, N. R. Org. React. 1975, 1.
92. Also see: (a) Ito, H.; Taguchi, T. Chem. Soc. Rev. 1999, 28, 43. (b) Enders, D.; Knopp, M.; Schiffers, R. Tetrahedron: Asymmetry 1996, 7, 1847. (c) Blechert, S. Synthesis 1989, 71. (d) Kallmerten, J.; Wittman, M. D. Stud. Nat. Prod. Chem. 1989, 3, 233. (e) Ziegler, F. E. Chem. Rev. 1988, 88, 1423. (f) Murray, A. W. Org. React. Mech. 1987, 457. (g) Murray, A. W. Org. React. Mech. 1986, 429. (h) Moody, C. J. Adv. Heterocycl. Chem. 1987, 42, 203. (i) Barlett, P. A. Tetrahedron 1980, 36, 3. (j) Lutz, R. P. Chem. Rev. 1984, 84, 205. (k) Rhoads, S. J.; Raulins, N. R. Org. React. 1975, 1.
93. Also see: (a) Ito, H.; Taguchi, T. Chem. Soc. Rev. 1999, 28, 43. (b) Enders, D.; Knopp, M.; Schiffers, R. Tetrahedron: Asymmetry 1996, 7, 1847. (c) Blechert, S. Synthesis 1989, 71. (d) Kallmerten, J.; Wittman, M. D. Stud. Nat. Prod. Chem. 1989, 3, 233. (e) Ziegler, F. E. Chem. Rev. 1988, 88, 1423. (f) Murray, A. W. Org. React. Mech. 1987, 457. (g) Murray, A. W. Org. React. Mech. 1986, 429. (h) Moody, C. J. Adv. Heterocycl. Chem. 1987, 42, 203. (i) Barlett, P. A. Tetrahedron 1980, 36, 3. (j) Lutz, R. P. Chem. Rev. 1984, 84, 205. (k) Rhoads, S. J.; Raulins, N. R. Org. React. 1975, 1.
94. Also see: (a) Ito, H.; Taguchi, T. Chem. Soc. Rev. 1999, 28, 43. (b) Enders, D.; Knopp, M.; Schiffers, R. Tetrahedron: Asymmetry 1996, 7, 1847. (c) Blechert, S. Synthesis 1989, 71. (d) Kallmerten, J.; Wittman, M. D. Stud. Nat. Prod. Chem. 1989, 3, 233. (e) Ziegler, F. E. Chem. Rev. 1988, 88, 1423. (f) Murray, A. W. Org. React. Mech. 1987, 457. (g) Murray, A. W. Org. React. Mech. 1986, 429. (h) Moody, C. J. Adv. Heterocycl. Chem. 1987, 42, 203. (i) Barlett, P. A. Tetrahedron 1980, 36, 3. (j) Lutz, R. P. Chem. Rev. 1984, 84, 205. (k) Rhoads, S. J.; Raulins, N. R. Org. React. 1975, 1.
95. Also see: (a) Ito, H.; Taguchi, T. Chem. Soc. Rev. 1999, 28, 43. (b) Enders, D.; Knopp, M.; Schiffers, R. Tetrahedron: Asymmetry 1996, 7, 1847. (c) Blechert, S. Synthesis 1989, 71. (d) Kallmerten, J.; Wittman, M. D. Stud. Nat. Prod. Chem. 1989, 3, 233. (e) Ziegler, F. E. Chem. Rev. 1988, 88, 1423. (f) Murray, A. W. Org. React. Mech. 1987, 457. (g) Murray, A. W. Org. React. Mech. 1986, 429. (h) Moody, C. J. Adv. Heterocycl. Chem. 1987, 42, 203. (i) Barlett, P. A. Tetrahedron 1980, 36, 3. (j) Lutz, R. P. Chem. Rev. 1984, 84, 205. (k) Rhoads, S. J.; Raulins, N. R. Org. React. 1975, 1.
96. Also see: (a) Ito, H.; Taguchi, T. Chem. Soc. Rev. 1999, 28, 43. (b) Enders, D.; Knopp, M.; Schiffers, R. Tetrahedron: Asymmetry 1996, 7, 1847. (c) Blechert, S. Synthesis 1989, 71. (d) Kallmerten, J.; Wittman, M. D. Stud. Nat. Prod. Chem. 1989, 3, 233. (e) Ziegler, F. E. Chem. Rev. 1988, 88, 1423. (f) Murray, A. W. Org. React. Mech. 1987, 457. (g) Murray, A. W. Org. React. Mech. 1986, 429. (h) Moody, C. J. Adv. Heterocycl. Chem. 1987, 42, 203. (i) Barlett, P. A. Tetrahedron 1980, 36, 3. (j) Lutz, R. P. Chem. Rev. 1984, 84, 205. (k) Rhoads, S. J.; Raulins, N. R. Org. React. 1975, 1.
97. Also see: (a) Ito, H.; Taguchi, T. Chem. Soc. Rev. 1999, 28, 43. (b) Enders, D.; Knopp, M.; Schiffers, R. Tetrahedron: Asymmetry 1996, 7, 1847. (c) Blechert, S. Synthesis 1989, 71. (d) Kallmerten, J.; Wittman, M. D. Stud. Nat. Prod. Chem. 1989, 3, 233. (e) Ziegler, F. E. Chem. Rev. 1988, 88, 1423. (f) Murray, A. W. Org. React. Mech. 1987, 457. (g) Murray, A. W. Org. React. Mech. 1986, 429. (h) Moody, C. J. Adv. Heterocycl. Chem. 1987, 42, 203. (i) Barlett, P. A. Tetrahedron 1980, 36, 3. (j) Lutz, R. P. Chem. Rev. 1984, 84, 205. (k) Rhoads, S. J.; Raulins, N. R. Org. React. 1975, 1.
98. Also see: (a) Ito, H.; Taguchi, T. Chem. Soc. Rev. 1999, 28, 43. (b) Enders, D.; Knopp, M.; Schiffers, R. Tetrahedron: Asymmetry 1996, 7, 1847. (c) Blechert, S. Synthesis 1989, 71. (d) Kallmerten, J.; Wittman, M. D. Stud. Nat. Prod. Chem. 1989, 3, 233. (e) Ziegler, F. E. Chem. Rev. 1988, 88, 1423. (f) Murray, A. W. Org. React. Mech. 1987, 457. (g) Murray, A. W. Org. React. Mech. 1986, 429. (h) Moody, C. J. Adv. Heterocycl. Chem. 1987, 42, 203. (i) Barlett, P. A. Tetrahedron 1980, 36, 3. (j) Lutz, R. P. Chem. Rev. 1984, 84, 205. (k) Rhoads, S. J.; Raulins, N. R. Org. React. 1975, 1.
99. Also see: (a) Ito, H.; Taguchi, T. Chem. Soc. Rev. 1999, 28, 43. (b) Enders, D.; Knopp, M.; Schiffers, R. Tetrahedron: Asymmetry 1996, 7, 1847. (c) Blechert, S. Synthesis 1989, 71. (d) Kallmerten, J.; Wittman, M. D. Stud. Nat. Prod. Chem. 1989, 3, 233. (e) Ziegler, F. E. Chem. Rev. 1988, 88, 1423. (f) Murray, A. W. Org. React. Mech. 1987, 457. (g) Murray, A. W. Org. React. Mech. 1986, 429. (h) Moody, C. J. Adv. Heterocycl. Chem. 1987, 42, 203. (i) Barlett, P. A. Tetrahedron 1980, 36, 3. (j) Lutz, R. P. Chem. Rev. 1984, 84, 205. (k) Rhoads, S. J.; Raulins, N. R. Org. React. 1975, 1.
100. Also see: (a) Ito, H.; Taguchi, T. Chem. Soc. Rev. 1999, 28, 43. (b) Enders, D.; Knopp, M.; Schiffers, R. Tetrahedron: Asymmetry 1996, 7, 1847. (c) Blechert, S. Synthesis 1989, 71. (d) Kallmerten, J.; Wittman, M. D. Stud. Nat. Prod. Chem. 1989, 3, 233. (e) Ziegler, F. E. Chem. Rev. 1988, 88, 1423. (f) Murray, A. W. Org. React. Mech. 1987, 457. (g) Murray, A. W. Org. React. Mech. 1986, 429. (h) Moody, C. J. Adv. Heterocycl. Chem. 1987, 42, 203. (i) Barlett, P. A. Tetrahedron 1980, 36, 3. (j) Lutz, R. P. Chem. Rev. 1984, 84, 205. (k) Rhoads, S. J.; Raulins, N. R. Org. React. 1975, 1.
101. Also see: (a) Ito, H.; Taguchi, T. Chem. Soc. Rev. 1999, 28, 43. (b) Enders, D.; Knopp, M.; Schiffers, R. Tetrahedron: Asymmetry 1996, 7, 1847. (c) Blechert, S. Synthesis 1989, 71. (d) Kallmerten, J.; Wittman, M. D. Stud. Nat. Prod. Chem. 1989, 3, 233. (e) Ziegler, F. E. Chem. Rev. 1988, 88, 1423. (f) Murray, A. W. Org. React. Mech. 1987, 457. (g) Murray, A. W. Org. React. Mech. 1986, 429. (h) Moody, C. J. Adv. Heterocycl. Chem. 1987, 42, 203. (i) Barlett, P. A. Tetrahedron 1980, 36, 3. (j) Lutz, R. P. Chem. Rev. 1984, 84, 205. (k) Rhoads, S. J.; Raulins, N. R. Org. React. 1975, 1.
102. (a) Ficini, J.; Lumbroso-Bader, N.; Pouliquen, J. Tetrahedron Lett. 1968, 9, 4139.
103. (b) Ficini, J.; Barbara, C. Tetrahedron Lett. 1966, 7, 6425.
104. (c) Nakai, T.; Setoi, H.; Kageyama, Y. Tetrahedron Lett. 1981, 22, 4097.
105. For recent reviews on metathesis see: (a) Grubbs, R. H.; Miller, S. J.; Fu, G. C. Acc. Chem. Res. 1995, 28, 446. (b) Shrock, R. R. Tetrahedron 1999, 55, 8141. (c) Fürstner, A. Angew. Chem. Int. Ed. 2000, 39, 3012. (d) Trnka, T. M.; Grubbs, R. H. Acc. Chem. Res. 2001, 34, 18. (e) Hoveyda, A. H.; Schrock, R. R. Chem.-Eur. J. 2001, 7, 945.
106. For recent reviews on metathesis see: (a) Grubbs, R. H.; Miller, S. J.; Fu, G. C. Acc. Chem. Res. 1995, 28, 446. (b) Shrock, R. R. Tetrahedron 1999, 55, 8141. (c) Fürstner, A. Angew. Chem. Int. Ed. 2000, 39, 3012. (d) Trnka, T. M.; Grubbs, R. H. Acc. Chem. Res. 2001, 34, 18. (e) Hoveyda, A. H.; Schrock, R. R. Chem.-Eur. J. 2001, 7, 945.
107. For recent reviews on metathesis see: (a) Grubbs, R. H.; Miller, S. J.; Fu, G. C. Acc. Chem. Res. 1995, 28, 446. (b) Shrock, R. R. Tetrahedron 1999, 55, 8141. (c) Fürstner, A. Angew. Chem. Int. Ed. 2000, 39, 3012. (d) Trnka, T. M.; Grubbs, R. H. Acc. Chem. Res. 2001, 34, 18. (e) Hoveyda, A. H.; Schrock, R. R. Chem.-Eur. J. 2001, 7, 945.
108. For recent reviews on metathesis see: (a) Grubbs, R. H.; Miller, S. J.; Fu, G. C. Acc. Chem. Res. 1995, 28, 446. (b) Shrock, R. R. Tetrahedron 1999, 55, 8141. (c) Fürstner, A. Angew. Chem. Int. Ed. 2000, 39, 3012. (d) Trnka, T. M.; Grubbs, R. H. Acc. Chem. Res. 2001, 34, 18. (e) Hoveyda, A. H.; Schrock, R. R. Chem.-Eur. J. 2001, 7, 945.
109. For recent reviews on metathesis see: (a) Grubbs, R. H.; Miller, S. J.; Fu, G. C. Acc. Chem. Res. 1995, 28, 446. (b) Shrock, R. R. Tetrahedron 1999, 55, 8141. (c) Fürstner, A. Angew. Chem. Int. Ed. 2000, 39, 3012. (d) Trnka, T. M.; Grubbs, R. H. Acc. Chem. Res. 2001, 34, 18. (e) Hoveyda, A. H.; Schrock, R. R. Chem.-Eur. J. 2001, 7, 945.
110. For reviews on enyne RCM see: (a) Mori, M. In Topics in Organometallic Chemistry, Vol. 1; Fürstner, A., Ed.; Springer-Verlag: Berlin Heidelberg, 1998, 133. (b) Mori, M. J. Synth. Org. Chem. Jpn. 1998, 56, 115.
111. For reviews on enyne RCM see: (a) Mori, M. In Topics in Organometallic Chemistry, Vol. 1; Fürstner, A., Ed.; Springer-Verlag: Berlin Heidelberg, 1998, 133. (b) Mori, M. J. Synth. Org. Chem. Jpn. 1998, 56, 115.
112. For recent applications of enyne metathesis see: (a) Clark, J. S.; Hamelin, O. Angew. Chem. Int. Ed. 2000, 39, 372. (b) Fürstner, A.; Szillat, H.; Stelzer, F. J. Am. Chem. Soc. 2000, 122, 6785. (c) Stragies, R.; Voigtmann, U.; Blechert, S. Tetrahedron Lett. 2000, 41, 5465. (d) Fürstner, A.; Ackermann, L.; Gabor, B.; Goddard, R.; Lehmann, C. W.; Mynott, R.; Stelzer, F.; Thiel, O. R. Chem.-Eur. J. 2001, 7, 3236. (e) Kitamura, T.; Mori, M. Org. Lett. 2001, 3, 1161. (f) Mori, M.; Kitamura, T.; Sato, Y. Synthesis 2001, 654.
113. For recent applications of enyne metathesis see: (a) Clark, J. S.; Hamelin, O. Angew. Chem. Int. Ed. 2000, 39, 372. (b) Fürstner, A.; Szillat, H.; Stelzer, F. J. Am. Chem. Soc. 2000, 122, 6785. (c) Stragies, R.; Voigtmann, U.; Blechert, S. Tetrahedron Lett. 2000, 41, 5465. (d) Fürstner, A.; Ackermann, L.; Gabor, B.; Goddard, R.; Lehmann, C. W.; Mynott, R.; Stelzer, F.; Thiel, O. R. Chem.-Eur. J. 2001, 7, 3236. (e) Kitamura, T.; Mori, M. Org. Lett. 2001, 3, 1161. (f) Mori, M.; Kitamura, T.; Sato, Y. Synthesis 2001, 654.
114. For recent applications of enyne metathesis see: (a) Clark, J. S.; Hamelin, O. Angew. Chem. Int. Ed. 2000, 39, 372. (b) Fürstner, A.; Szillat, H.; Stelzer, F. J. Am. Chem. Soc. 2000, 122, 6785. (c) Stragies, R.; Voigtmann, U.; Blechert, S. Tetrahedron Lett. 2000, 41, 5465. (d) Fürstner, A.; Ackermann, L.; Gabor, B.; Goddard, R.; Lehmann, C. W.; Mynott, R.; Stelzer, F.; Thiel, O. R. Chem.-Eur. J. 2001, 7, 3236. (e) Kitamura, T.; Mori, M. Org. Lett. 2001, 3, 1161. (f) Mori, M.; Kitamura, T.; Sato, Y. Synthesis 2001, 654.
115. For recent applications of enyne metathesis see: (a) Clark, J. S.; Hamelin, O. Angew. Chem. Int. Ed. 2000, 39, 372. (b) Fürstner, A.; Szillat, H.; Stelzer, F. J. Am. Chem. Soc. 2000, 122, 6785. (c) Stragies, R.; Voigtmann, U.; Blechert, S. Tetrahedron Lett. 2000, 41, 5465. (d) Fürstner, A.; Ackermann, L.; Gabor, B.; Goddard, R.; Lehmann, C. W.; Mynott, R.; Stelzer, F.; Thiel, O. R. Chem.-Eur. J. 2001, 7, 3236. (e) Kitamura, T.; Mori, M. Org. Lett. 2001, 3, 1161. (f) Mori, M.; Kitamura, T.; Sato, Y. Synthesis 2001, 654.
116. For recent applications of enyne metathesis see: (a) Clark, J. S.; Hamelin, O. Angew. Chem. Int. Ed. 2000, 39, 372. (b) Fürstner, A.; Szillat, H.; Stelzer, F. J. Am. Chem. Soc. 2000, 122, 6785. (c) Stragies, R.; Voigtmann, U.; Blechert, S. Tetrahedron Lett. 2000, 41, 5465. (d) Fürstner, A.; Ackermann, L.; Gabor, B.; Goddard, R.; Lehmann, C. W.; Mynott, R.; Stelzer, F.; Thiel, O. R. Chem.-Eur. J. 2001, 7, 3236. (e) Kitamura, T.; Mori, M. Org. Lett. 2001, 3, 1161. (f) Mori, M.; Kitamura, T.; Sato, Y. Synthesis 2001, 654.
117. For recent applications of enyne metathesis see: (a) Clark, J. S.; Hamelin, O. Angew. Chem. Int. Ed. 2000, 39, 372. (b) Fürstner, A.; Szillat, H.; Stelzer, F. J. Am. Chem. Soc. 2000, 122, 6785. (c) Stragies, R.; Voigtmann, U.; Blechert, S. Tetrahedron Lett. 2000, 41, 5465. (d) Fürstner, A.; Ackermann, L.; Gabor, B.; Goddard, R.; Lehmann, C. W.; Mynott, R.; Stelzer, F.; Thiel, O. R. Chem.-Eur. J. 2001, 7, 3236. (e) Kitamura, T.; Mori, M. Org. Lett. 2001, 3, 1161. (f) Mori, M.; Kitamura, T.; Sato, Y. Synthesis 2001, 654.
118. Hoye, T. R.; Donaldson, S. M.; Vos, T. J. Org. Lett. 1999, 1, 277.
119. For silyl ynol ethers see: (a) Schramm, M. P.; Reddy, D. S.; Kozmin, S. A. Angew. Chem. Int. Ed. 2001, 40, 4274. (b) For an earlier account on sugar substituted alkynol ethers see: Clark, J. S.; Hamelin, O. Angew Chem. Int. Ed. 2000, 39, 372. (c) For phosphonamides see: Timmer, M. S. M.; Ovaa, H.; Filippov, D. V.; Van der Marel, G. A.; Van Boom, J. H. Tetrahedron Lett. 2001, 42, 8231.
120. For silyl ynol ethers see: (a) Schramm, M. P.; Reddy, D. S.; Kozmin, S. A. Angew. Chem. Int. Ed. 2001, 40, 4274. (b) For an earlier account on sugar substituted alkynol ethers see: Clark, J. S.; Hamelin, O. Angew Chem. Int. Ed. 2000, 39, 372. (c) For phosphonamides see: Timmer, M. S. M.; Ovaa, H.; Filippov, D. V.; Van der Marel, G. A.; Van Boom, J. H. Tetrahedron Lett. 2001, 42, 8231.
121. For silyl ynol ethers see: (a) Schramm, M. P.; Reddy, D. S.; Kozmin, S. A. Angew. Chem. Int. Ed. 2001, 40, 4274. (b) For an earlier account on sugar substituted alkynol ethers see: Clark, J. S.; Hamelin, O. Angew Chem. Int. Ed. 2000, 39, 372. (c) For phosphonamides see: Timmer, M. S. M.; Ovaa, H.; Filippov, D. V.; Van der Marel, G. A.; Van Boom, J. H. Tetrahedron Lett. 2001, 42, 8231.
122. For some earlier work see: (a) Weskamp, T.; Schattenmann, W. C.; Spiegler, M.; Herrmann, W. A. Angew. Chem. Int. Ed. 1998, 37, 2490. (b) Herrmann, W. A.; Köcher, C. Angew. Chem., Int. Ed. Engl. 1997, 36, 2162.
123. For some earlier work see: (a) Weskamp, T.; Schattenmann, W. C.; Spiegler, M.; Herrmann, W. A. Angew. Chem. Int. Ed. 1998, 37, 2490. (b) Herrmann, W. A.; Köcher, C. Angew. Chem., Int. Ed. Engl. 1997, 36, 2162.
124. (a) Huang, J.; Stevens, E. D.; Nolan, S. P.; Petersen, J. L. J. Am. Chem. Soc. 1999, 121, 2674; and references cited therein.
125. (b) Huang, J.; Schanz, H.-J.; Stevens, E. D.; Nolan, S. P. Organometallics 1999, 18, 2370.
126. Scholl, M.; Ding, S.; Lee, C. W.; Grubbs, R. H. Org. Lett. 1999, 1, 953.
127. For other methods for syntheses of ynamides see: (a) ref. 8 (b) Fromont, C.; Masson, S. Tetrahedron 1999, 55, 5405. (c) Novikov, M. S.; Khlebnikov, A. F.; Kostikov, R. R. Russ. J. Org. Chem. 1991, 27, 1576. (d) Tikhomirov, D. A.; Eremeev, A. V. Chem. Heterocycl. Comp. 1987, 23, 1141.
128. For other methods for syntheses of ynamides see: (a) ref. 8 (b) Fromont, C.; Masson, S. Tetrahedron 1999, 55, 5405. (c) Novikov, M. S.; Khlebnikov, A. F.; Kostikov, R. R. Russ. J. Org. Chem. 1991, 27, 1576. (d) Tikhomirov, D. A.; Eremeev, A. V. Chem. Heterocycl. Comp. 1987, 23, 1141.
129. For other methods for syntheses of ynamides see: (a) ref. 8 (b) Fromont, C.; Masson, S. Tetrahedron 1999, 55, 5405. (c) Novikov, M. S.; Khlebnikov, A. F.; Kostikov, R. R. Russ. J. Org. Chem. 1991, 27, 1576. (d) Tikhomirov, D. A.; Eremeev, A. V. Chem. Heterocycl. Comp. 1987, 23, 1141.
130. For other methods for syntheses of ynamides see: (a) ref. 8 (b) Fromont, C.; Masson, S. Tetrahedron 1999, 55, 5405. (c) Novikov, M. S.; Khlebnikov, A. F.; Kostikov, R. R. Russ. J. Org. Chem. 1991, 27, 1576. (d) Tikhomirov, D. A.; Eremeev, A. V. Chem. Heterocycl. Comp. 1987, 23, 1141.
131. For a review on copper mediated C-N and C-O bond formation see: (a) Lindley, J. Tetrahedron 1984, 40, 1433. (b) Goldberg, I. Ber. Dtsch. Chem. Ges. 1906, 39, 1691. (cYamamoto, T.; Kurata, Y. Can. J. Chem. 1983, 61, 86. (c) Yamamoto, T.; Ehara, Y.; Kubota, M.; Yamamoto, A. Bull. Chem. Soc. Jpn. 1980, 53, 1299. (d) Yamamoto, T. Synth. Commun. 1979, 9, 219.
132. For a review on copper mediated C-N and C-O bond formation see: (a) Lindley, J. Tetrahedron 1984, 40, 1433. (b) Goldberg, I. Ber. Dtsch. Chem. Ges. 1906, 39, 1691. (cYamamoto, T.; Kurata, Y. Can. J. Chem. 1983, 61, 86. (c) Yamamoto, T.; Ehara, Y.; Kubota, M.; Yamamoto, A. Bull. Chem. Soc. Jpn. 1980, 53, 1299. (d) Yamamoto, T. Synth. Commun. 1979, 9, 219.
133. For a review on copper mediated C-N and C-O bond formation see: (a) Lindley, J. Tetrahedron 1984, 40, 1433. (b) Goldberg, I. Ber. Dtsch. Chem. Ges. 1906, 39, 1691. (cYamamoto, T.; Kurata, Y. Can. J. Chem. 1983, 61, 86. (c) Yamamoto, T.; Ehara, Y.; Kubota, M.; Yamamoto, A. Bull. Chem. Soc. Jpn. 1980, 53, 1299. (d) Yamamoto, T. Synth. Commun. 1979, 9, 219.
134. For a review on copper mediated C-N and C-O bond formation see: (a) Lindley, J. Tetrahedron 1984, 40, 1433. (b) Goldberg, I. Ber. Dtsch. Chem. Ges. 1906, 39, 1691. (cYamamoto, T.; Kurata, Y. Can. J. Chem. 1983, 61, 86. (c) Yamamoto, T.; Ehara, Y.; Kubota, M.; Yamamoto, A. Bull. Chem. Soc. Jpn. 1980, 53, 1299. (d) Yamamoto, T. Synth. Commun. 1979, 9, 219.
135. For a review on copper mediated C-N and C-O bond formation see: (a) Lindley, J. Tetrahedron 1984, 40, 1433. (b) Goldberg, I. Ber. Dtsch. Chem. Ges. 1906, 39, 1691. (cYamamoto, T.; Kurata, Y. Can. J. Chem. 1983, 61, 86. (c) Yamamoto, T.; Ehara, Y.; Kubota, M.; Yamamoto, A. Bull. Chem. Soc. Jpn. 1980, 53, 1299. (d) Yamamoto, T. Synth. Commun. 1979, 9, 219.
136. Key papers from Buchwald's group: (a) Klapper, A.; Huang, X.; Buchwald, S. L. J. Am. Chem. Soc. 2002, 124, 7421. (b) Klapars, A.; Antilla, J. C.; Huang, X.; Buchwald, S. L. J. Am. Chem. Soc. 2001, 123, 7727. (c) Kwong, F. Y.; Klapars, A.; Buchwald, S. L. Org. Lett. 2002, 4, 581.
137. Key papers from Buchwald's group: (a) Klapper, A.; Huang, X.; Buchwald, S. L. J. Am. Chem. Soc. 2002, 124, 7421. (b) Klapars, A.; Antilla, J. C.; Huang, X.; Buchwald, S. L. J. Am. Chem. Soc. 2001, 123, 7727. (c) Kwong, F. Y.; Klapars, A.; Buchwald, S. L. Org. Lett. 2002, 4, 581.
138. Key papers from Buchwald's group: (a) Klapper, A.; Huang, X.; Buchwald, S. L. J. Am. Chem. Soc. 2002, 124, 7421. (b) Klapars, A.; Antilla, J. C.; Huang, X.; Buchwald, S. L. J. Am. Chem. Soc. 2001, 123, 7727. (c) Kwong, F. Y.; Klapars, A.; Buchwald, S. L. Org. Lett. 2002, 4, 581.
139. For recent references of copper catalyzed N-arylations of amides and enamides: (a) Shen, R.; Porco, J. A. Jr. Org. Lett. 2002, 2, 1333. (b) Yamada, K.; Kubo, T.; Tokuyama, H.; Fukuyama, T. Synlett 2002, 231. (c) Lam, P. Y. S.; Deudon, S.; Averill, K. M.; Li, R.; He, M. Y.; DeShong, P.; Clark, C. G. J. Am. Chem. Soc. 2000, 122, 7600.
140. For recent references of copper catalyzed N-arylations of amides and enamides: (a) Shen, R.; Porco, J. A. Jr. Org. Lett. 2002, 2, 1333. (b) Yamada, K.; Kubo, T.; Tokuyama, H.; Fukuyama, T. Synlett 2002, 231. (c) Lam, P. Y. S.; Deudon, S.; Averill, K. M.; Li, R.; He, M. Y.; DeShong, P.; Clark, C. G. J. Am. Chem. Soc. 2000, 122, 7600.
141. For recent references of copper catalyzed N-arylations of amides and enamides: (a) Shen, R.; Porco, J. A. Jr. Org. Lett. 2002, 2, 1333. (b) Yamada, K.; Kubo, T.; Tokuyama, H.; Fukuyama, T. Synlett 2002, 231. (c) Lam, P. Y. S.; Deudon, S.; Averill, K. M.; Li, R.; He, M. Y.; DeShong, P.; Clark, C. G. J. Am. Chem. Soc. 2000, 122, 7600.
142. Frederick, M. O.; Mulder, J. A.; Tracey, M. R.; Hsung, R. P.; Huang, J.; Kurtz, K. C. M.; Shen, L.; Douglas, C. J. J. Am. Chem. Soc. 2003, 125, 2368.