Stereoselective palladium-catalyzed functionalization of homoallylic alcohols: A convenient synthesis of di- and trisubstituted isoxazolidines and β-amino-δ-hydroxy esters

Chemistry - A European Journal

Volumn 18, Issue 22, 2012, Pages 6873-6884

  Malkov, Andrei V ^a,b   Barłõg, MacIej ^a,c   Miller Potucká, Lucie ^a,d   Kabeshov, Mikhail A ^a,b   Farrugia, Louis J ^a   Kočovský, Pavel ^a  

^a UNIVERSITY OF GLASGOW   (United Kingdom)

^b LOUGHBOROUGH UNIVERSITY   (United Kingdom)

^c TEXAS A AND M UNIVERSITY AT QATAR   (Qatar)

^d ASTRAZENECA   (United Kingdom)

Author keywords

amidopalladation; amino acids; carbonylation; palladium; stereocontrol

Indexed keywords

ALKOXYAMINES; AMIDATION; AMIDOPALLADATION; CARBONYLATIVE CYCLIZATION; DIASTEREO-SELECTIVITY; DIASTEREOISOMERS; DIASTEREOSELECTIVE; ENANTIOPURE; FUNCTIONALIZATIONS; HOMOALLYLIC ALCOHOL; HYDROXY ACIDS; HYDROXY ESTERS; ISOXAZOLIDINES; NITROGEN NUCLEOPHILES; PALLADIUM-CATALYZED; RING CLOSINGS; STEREO-SELECTIVE; STEREOCONTROL; SYN-ADDITION;

AMINO ACIDS; CARBONYLATION; CARBOXYLIC ACIDS; CATALYSIS; ESTERIFICATION; ESTERS; PALLADIUM; STEREOSELECTIVITY;

CYCLIZATION;

EID: 84861558045     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.201102716     Document Type: Article

References (230)

1. E. J. Corey, X.-M. Cheng, The Logic of Chemical Synthesis Wiley, New York, 1989
2. K. C. Nicolaou, E. J. Sorensen, Classics in Total Synthesis VCH, Weinheim, 1996
3. K. C. Nicolaou, S. A. Snyder, Classics in Total Synthesis II, Wiley-VCH, Weinheim, 2003
4. L. Kürti, B. Czakõ, Strategic Applications of Named Reactions in Organic Synthesis, Elsevier, Amsterdam, 2005
5. T. Hudlický, J. W. Reed, The Way of Synthesis, Wiley-VCH, Weinheim, 2007
6. P. Kočovský, F. Tureček, J. Hájí ček, Synthesis of Natural Products: Problems of Stereoselectivity, Vols. 1 and 2, CRC, Boca Raton, Florida, 1986.
7. "Electrophilic Additions to C=X Bonds": G. H. Schmid, D. G. Garratt, in The Chemistry of Double Bonded Functional Groups, Part 2 (Ed.:, S. Patai,), Wiley, New York, 1977, p. 725
8. "Electrophilic Additions to C=X Bonds": P. Koč ovský, in Chemistry of Functional Groups, Supp. A3: The Chemistry of Double-Bonded Functional Groups (Ed.:, S. Patai,), Wiley, Chichester, 1997, p. 1135
9. M. G. Finn, K. B. Sharpless, in Asymmetric Synthesis Vol. 5 (Ed.:, J. D. Morrison,), Academic Press, New York, 1985, p. 247.
10. P. A. Bartlett, Tetrahedron 1980, 36, 2
11. G. Cardillo, M. Orena, Tetrahedron 1990, 46, 3321
12. S. Robin, G. Rousseau, Eur. J. Org. Chem. 2002, 3099.
13. A. Castellanos, S. P. Fletcher, Chem. Eur. J. 2011, 17, 5766. For recent examples of enantioselective halolactonization, see
14. G. E. Veitch, E. N. Jacobsen, Angew. Chem. 2010, 122, 7490
15. Angew. Chem. Int. Ed. 2010, 49, 7332
16. G. Chen, S. Ma, Angew. Chem. 2010, 122, 8484
17. Angew. Chem. Int. Ed. 2010, 49, 8306
18. K. Murai, T. Matsushita, A. Nakamura, S. Fukushima, M. Shimura, H. Fujioka, Angew. Chem. 2010, 122, 9360
19. Angew. Chem. Int. Ed. 2010, 49, 9174
20. M. R. Monaco, M. Bella, Angew. Chem. 2011, 123, 11238
21. Angew. Chem. Int. Ed. 2011, 50, 11044.
22. P. Kočovský, M. Pour, J. Org. Chem. 1990, 50, 5580 and references cited therein.
23. R. B. Woodward, F. E. Bader, H. Bickel, A. J. Frey, R. W. Kierstead, Tetrahedron 1958, 2, 1
24. R. B. Woodward, J. Gosteli, I. Ernest, R. J. Friary, G. Nestler, H. Raman, R. Sitrin, C. Suter, J. K. Whitesell, J. Am. Chem. Soc. 1973, 95, 6853
25. P. Kočovský, F. Tureček, Tetrahedron Lett. 1981, 22, 2699
26. P. Kočovský, I. Stieborová, Tetrahedron Lett. 1989, 30, 4295
27. P. Kočovský, I. Starý, J. Zajíček, F. Tureček, S. Vašíčková, J. Chem Soc. Perkin Trans 1 1988, 2297.
28. R. D. Walkup, G. Par, Tetrahedron Lett. 1987, 28, 1023
29. A. B. Reitz, S. O. Nortey, B. E. Maryanoff, J. Org. Chem. 1987, 52, 4191
30. H. Takahata, Y. Banba, M. Tajima, T. Momose, J. Org. Chem. 1991, 56, 240
31. P. Kočovský, Organometallics 1993, 12, 1969
32. P. Kočovský, J. Šrogl, A. Gogoll, V. Hanuš, M. Polášek, J. Chem. Soc. Chem. Commun. 1992, 1086
33. P. Kočovský, J. Šrogl, M. Pour, A. Gogoll, J. Am. Chem. Soc. 1994, 116, 186
34. P. Kočovský, J. M. Grech, W. L. Mitchell, J. Org. Chem. 1995, 60, 1482
35. P. Kočovský, J. M. Grech, W. L. Mitchell, Tetrahedron Lett. 1996, 37, 1125
36. P. Kočovský, V. Dunn, J. M. Grech, J. Šrogl, W. L. Mitchell, Tetrahedron Lett. 1996, 37, 5585
37. III, see
38. J. P. Michael, P. C. Ting, P. A. Bartlett, J. Org. Chem. 1985, 50, 2416
39. P. Kočovský, V. Langer, A. Gogoll, J. Chem. Soc. Chem. Commun. 1990, 1026
40. P. Kočovský, R. S. Baines, J. Org. Chem. 1994, 59, 5439. Au
41. A. S. K. Hashmi, L. Schwarz, L.; J.-H. Choi, T. M. Frost, Angew. Chem. 2000, 112, 2382
42. J.-H. Choi, T. M. Frost, Angew. Chem. 2000, 112, 2382
43. Angew. Chem. Int. Ed. 2000, 39, 2285
44. M. Rudolph, A. S. K. Hashmi, Chem. Commun. 2011, 47, 6536.
45. E. Negishi, Organopalladium Chemistry for Organic Synthesis, Wiley, New York, 2002.
46. J. Tsuji, Palladium Reagents and Catalysts: Innovations in Organic Synthesis Wiley, Chichester, 1995.
47. M. F. Semmelhack, C. Bodurow, J. Am. Chem. Soc. 1984, 106, 1496
48. for correction, see:, M. F. Semmelhack, C. Bodurow, J. Am. Chem. Soc. 1984, 106, 5388.
49. M. F. Semmelhack, J. J. Bozell, T. Sato, W. Wulff, E. Spiess, A. Zask, J. Am. Chem. Soc. 1982, 104, 5850
50. M. F. Semmelhack, A. Zask, J. Am. Chem. Soc. 1983, 105, 2034
51. M. F. Semmelhack, C. Bodurow, M. Baum, Tetrahedron Lett. 1984, 25, 3171
52. M. F. Semmelhack, J. J. Bozell, L. Keller, T. Sato, E. J. Spiess, W. Wulff, A. Zask, Tetrahedron 1985, 41, 5803
53. M. F. Semmelhack, N. Zhang, J. Org. Chem. 1989, 54, 4483
54. M. F. Semmelhack, C. R. Kim, W. Bobler, M. Meier, Tetrahedron Lett. 1989, 30, 4925
55. M. F. Semmelhack, C. Kim, N. Zhang, C. Bodurow, M. Sanner, W. Dobler, M. Meier, Pure Appl. Chem. 1990, 62, 2035
56. M. F. Semmelhack, W. R. Epa, Tetrahedron Lett. 1993, 34, 7205.
57. L. S. Hegedus, G. F. Allen, D. J. Olsen, J. Am. Chem. Soc. 1980, 102, 3583
58. H. Alper, D. Leonard, J. Chem. Soc. Chem. Commun. 1985, 511
59. D. Lathbury, P. Vernon, T. Gallagher, Tetrahedron Lett. 1986, 27, 6009
60. L. S. Hegedus, T. A. Mulhern, H. Asada, J. Am. Chem. Soc. 1986, 108, 6224
61. Y. Tamaru, M. Hojo, H. Higashimura, Z. Yoshida, J. Am. Chem. Soc. 1988, 110, 3994
62. Y. Tamaru, S. Kawamura, T. Bando, K. Tanaka, M. Hojo, Z. Yoshida, J. Org. Chem. 1988, 53, 5491
63. Y. Tamaru, M. Hojo, Z. Yoshida, J. Org. Chem. 1988, 53, 5731
64. M. McCormick, R. Monahan, J. Soria, D. Goldsmith, D. Liotta, J. Org. Chem. 1989, 54, 4485
65. Y. Tamaru, M. Hojo, Z. Yoshida, J. Org. Chem. 1991, 56, 1099
66. J.-Y. Lai, X.-X. Shi, Y.-S. Gong, L.-X. Dai, J. Org. Chem. 1993, 58, 4775
67. H. Qian, X. Han, R. A. Widenhoefer, J. Am. Chem. Soc. 2004, 126, 9536
68. C. Liu, R. A. Widenhoefer, Chem. Eur. J. 2006, 12, 2371
69. H. Harayama, A. Abe, T. Sakado, M. Kimura, K. Fugami, S. Tanaka, Y. Tamaru, J. Org. Chem. 1997, 62, 2113
70. T. A. Cernak, T. H. Lambert, J. Am. Chem. Soc. 2009, 131, 3124
71. J. R. Harris, S. R. Waetzig, K. A. Woerpel, Org. Lett. 2009, 11, 3290
72. K. H. Jensen, T. P. Pathak, Y. Zhang, M. S. Sigman, J. Am. Chem. Soc. 2009, 131, 17074
73. L. M. Ambrosini, T. A. Cernak, T. H. Lambert, Synthesis 2010, 870. For related examples, where an anti-addition of Pd and an external oxygen nucleophile is assumed, see
74. E. Keinan, K. K. Seth, R. Lamed, J. Am. Chem. Soc. 1986, 108, 3474. For cascade reactions involving Pd-catalyzed ring closure, see, for example
75. L. F. Tietze, K. M. Sommer, J. Zinngrebe, F. Stecker, Angew. Chem. 2005, 117, 262
76. L. F. Tietze, F. Stecker, J. Zinngrebe, K. M. Sommer, Chem. Eur. J. 2006, 12, 8770
77. L. F. Tietze, I. Hiriyakkanavar, H. P. Bell, Chem. Rev. 2004, 104, 3453
78. L. F. Tietze, N. Rackelmann, Pure Appl. Chem. 2004, 76, 1967
79. L. F. Tietze, T. Kinzel, Pure Appl. Chem. 2007, 79, 629.
80. Y. Tamaru, Z. Yoshida, J. Organomet. Chem. 1987, 334, 213
81. T. Hokosawa, S. Murahashi, Acc. Chem. Res. 1990, 23, 49
82. G. Zeni, R. C. Larock, Chem. Rev. 2004, 104, 2285
83. J. Muzart, Tetrahedron 2005, 61, 5955
84. J. P. Wolfe, M. B. Hay, Tetrahedron 2007, 63, 261
85. J. P. Wolfe, Eur. J. Org. Chem. 2007, 571
86. E. M. Beccalli, G. Broggini, M. Martinelli, S. Sottocomola, Chem. Rev. 2007, 107, 5318
87. I. Larrosa, P. Romea, F. Urpí, Tetrahedron 2008, 64, 2683
88. J. P. Wolfe, Synlett 2008, 2913
89. E. M. Beccalli, G. Broggini, A. Fasana, M. Rigamonti, J. Organomet. Chem. 2011, 696, 277.
90. P. Kočovský, V. Černý, M. Synáčková, Collect. Czech. Chem. Commun. 1979, 44, 1483
91. P. Kočovský, I. Stieborová, J. Chem. Soc. Perkin Trans. 1 1987, 1969.
92. J.-E. Bäckvall, Acc. Chem. Res. 1983, 16, 335
93. J.-E. Bäckvall, Pure Appl. Chem. 1992, 64, 429
94. "C-O and C-N Bond Formation Involving Conjugated Dienes and Allylpalladium Intermediates":, P. G. Andersson, J.-E. Bäckvall, in Organopalladium Chemistry for Organic Synthesis, Vol. 2 (Ed.:, E. Negishi,), Wiley, New York 2002, p. 1859.
95. J. Smidt, W. Hafner, R. Jira, J. Sedlmeier, R. Sieber, R. Rüttinger, H. Kojer, Angew. Chem. 1959, 71, 176
96. J. Smidt, W. Hafner, R. Jira, R. Sieber, J. Sedlmeier, A. Sabel, Angew. Chem. 1962, 74, 93
97. Angew. Chem. Eng. Transl. 1962, 1, 80
98. R. Jira, Angew. Chem. 2009, 121, 9196
99. Angew. Chem. Int. Ed. 2009, 48, 9034. For reviews on Wacker chemistry, see Ref. [8] and the following
100. J. A. Keith, P. M. Henry, Angew. Chem. 2009, 121, 9200
101. Angew. Chem. Int. Ed. 2009, 48, 9038.
102. II-catalyzed functionalization of alkenes via nucleopalladation, see:, R. I. McDonald, G. Liu, S. S. Stahl, Chem. Rev. 2011, 111, 2981.
103. I. Starý, P. Kočovský, J. Am. Chem. Soc. 1989, 111, 4981
104. I. Starý, J. Zajíček, P. Kočovský, Tetrahedron 1992, 48, 7229
105. C. N. Farthing, P. Kočovský, J. Am. Chem. Soc. 1998, 120, 6661
106. A. G. Jamieson, A. Sutherland, C. L. Willis, Org. Biomol. Chem. 2004, 2, 808 and references therein
107. A. G. Jamieson, A. Sutherland, Org. Biomol. Chem. 2005, 3, 735
108. A. G. Jamieson, A. Sutherland, Tetrahedron 2007, 63, 2123
109. M. D. Swift, A. Sutherland, Org. Lett. 2007, 9, 5239
110. A. M. Zaed, M. D. Swift, A. Sutherland, Org. Biomol. Chem. 2009, 7, 4996
111. A. G. Jamieson, A. Sutherland, Org. Lett. 2007, 9, 1609
112. K. N. Fanning, A. G. Jamieson, A. Sutherland, Org. Biomol. Chem. 2005, 3, 3749
113. M. D. Swift, A. Sutherland, Org. Biomol. Chem. 2006, 4, 3889
114. M. D. Swift, A. Sutherland, Tetrahedron 2008, 64, 9521
115. L. J. Drummond, A. Sutherland, Tetrahedron 2010, 66, 5349
116. N. K. Jobson, R. Spike, A. R. Crawford, D. Dewar, S. L. Pimlott, A. Sutherland, Org. Biomol. Chem. 2008, 6, 2369
117. N. K. Jobson, A. R. Crawford, D. Dewar, S. L. Pimlott, A. Sutherland, Bioorg. Med. Chem. Lett. 2009, 19, 4996. For an excellent review on steering effects in general, see
118. A. H. Hoveyda, D. A. Evans, G. C. Fu, Chem. Rev. 1993, 93, 1307. For a related precoordination of molybdenum, see the following
119. D. Dvořák, I. Starý, P. Kočovský, J. Am. Chem. Soc. 1995, 117, 6130
120. A. V. Malkov, I. R. Baxendale, D. Dvořák, D. J. Mansfield, P. Kočovský, J. Org. Chem. 1999, 64, 2737
121. P. Kočovský, A. V. Malkov, S. Vyskočil, G. C. Lloyd-Jones, Pure Appl. Chem. 1999, 71, 1425
122. A. V. Malkov, P. Spoor, V. Vinader, P. Kočovský, Tetrahedron Lett. 2001, 42, 509
123. G. C. Lloyd-Jones, S. W. Krska, D. L. Hughes, L. Gouriou, V. D. Bonet, K. Jack, Y. Sun, R. A. Reamer, J. Am. Chem. Soc. 2004, 126, 702
124. A. V. Malkov, L. Gouriou, G. C. Lloyd-Jones, I. Starý, V. Langer, P. Spoor, V. Vinader, P. Kočovský, Chem. Eur. J. 2006, 12, 6910.
125. T. Hayashi, K. Yamasaki, M. Mimura, Y. Uozumi, J. Am. Chem. Soc. 2004, 126, 3036.
126. R. M. Trend, Y. K. Ramtohul, B. M. Stoltz, J. Am. Chem. Soc. 2005, 127, 17778.
127. M. B. Hay, A. R. Hardin, J. P. Wolfe, J. Org. Chem. 2005, 70, 3099
128. M. B. Hay, J. P. Wolfe, Tetrahedron Lett. 2006, 47, 2793.
129. J. P. Wolfe, M. A. Rossi, J. Am. Chem. Soc. 2004, 126, 1620
130. M. B. Hay, J. P. Wolfe, J. Am. Chem. Soc. 2005, 127, 16468. For an overview, see Ref. [13i].
131. B. Åkermark, J.-E. Bäckvall, K. S. Hansén, K. Sjöberg, K. Zetterberg, Tetrahedron Lett. 1974, 15, 1363.
132. K. Isomura, N. Okada, M. Saruwatari, H. Yamasaki, H. Taniguchi, Chem. Lett. 1985, 385.
133. J. E. Ney, J. P. Wolfe, Angew. Chem. 2004, 116, 3689
134. Angew. Chem. Int. Ed. 2004, 43, 3605
135. M. B. Bertrand, J. D. Neukom, J. P. Wolfe, J. Org. Chem. 2008, 73, 8851.
136. J. S. Nakhla, J. W. Kampf, J. P. Wolfe, J. Am. Chem. Soc. 2006, 128, 2893.
137. J. D. Neukom, N. S. Perch, J. P. Wolfe, J. Am. Chem. Soc. 2010, 132, 6276
138. G. S. Lemen, N. C. Giampietro, M. B. Hay, J. P. Wolfe, J. Org. Chem. 2009, 74, 2533.
139. P. S. Hanley, D. Marković, J. F. Hartwig, J. Am. Chem. Soc. 2010, 132, 6302.
140. A. V. Malkov, M. Orsini, D. Pernazza, K. W. Muir, V. Langer, P. Meghani, P. Kočovský, Org. Lett. 2002, 4, 1047
141. A. V. Malkov, M. Bell, M. Vassieu, V. Bugatti, P. Kočovský, J. Mol. Catal. A 2003, 196, 179
142. A. V. Malkov, M. Bell, M. Orsini, D. Pernazza, A. Massa, P. Herrmann, P. Meghani, P. Kočovský, J. Org. Chem. 2003, 68, 9659
143. A. V. Malkov, M.-M. Westwater, A. Kadlčíková, A. Gutnov, J. Hodačová, Z. Rankovic, M. Kotora, P. Kočovský, Tetrahedron 2008, 64, 11335
144. A. V. Malkov, C. MacDonald, P. Kočovský, Tetrahedron: Asymmetry 2010, 21, 1173. For another application of pyridine N-oxides as organocatalysts, see
145. A. V. Malkov, M. R. Gordon, S. Stončius, J. Hussain, P. Kočovský, Org. Lett. 2009, 11, 5390.
146. M. Nakajima, M. Saito, M. Shiro, S. Hashimoto, J. Am. Chem. Soc. 1998, 120, 6419
147. M. Nakajima, M. Saito, M. Shiro, S. Hashimoto, Chem. Pharm. Bull. 2000, 48, 306
148. T. Shimada, A. Kina, S. Ikeda, T. Hayashi, Org. Lett. 2002, 4, 2799
149. T. Shimada, A. Kina, T. Hayashi, J. Org. Chem. 2003, 68, 6329
150. A. Kina, T. Shimada, T. Hayashi, Adv. Synth. Catal. 2004, 346, 1169
151. R. Hrdina, I. G. Stará, L. Dufková, S. Mitchell, I. Císařová, M. Kotora, Tetrahedron 2006, 62, 968
152. R. Hrdina, A. Kadlčíková, I. Valterová, J. Hodačová, M. Kotora, Tetrahedron: Asymmetry 2006, 17, 3185
153. R. Hrdina, I. Valterová, J. Hodačová, I. Císařová, M. Kotora, Adv. Synth. Catal. 2007, 349, 822
154. R. Hrdina, M. Dračínský, I. Valterová, J. Hodačová, I. Císařová, M. Kotora, Adv. Synth. Catal. 2008, 350, 1449
155. R. Hrdina, T. Boyd, I. Valterová, J. Hodačová, M. Kotora, Synlett 2008, 3141
156. A. Kadlčíková, R. Hrdina, I. Valterová, M. Kotora, Adv. Synth. Catal. 2009, 351, 1279
157. R. Hrdina, F. Opekar, J. Roithová, M. Kotora, Chem. Commun. 2009, 2314
158. A. Kadlčíková, I. Valterová, L. Ducháčková, J. Roithová, M. Kotora, Chem. Eur. J. 2010, 16, 9442
159. L. Ducháčková, A. Kadlčíková, M. Kotora, J. Roithová, J. Am. Chem. Soc. 2010, 132, 12660
160. K. Vlašaná, R. Hrdina, I. Valterová, M. Kotora, Eur. J. Org. Chem. 2010, 6040. For an overview, see
161. M. Kotora, Pure Appl. Chem. 2010, 82, 1813.
162. A. V. Malkov, M. Bell, F. Castelluzzo, P. Kočovský, Org. Lett. 2005, 7, 3219
163. A. V. Malkov, M. Barłõg, Y. Jewkes, J. Mikušek, P. Kočovský, J. Org. Chem. 2011, 76, 4800
164. A. V. Malkov, O. Kysilka, M. Edgar, A. Kadlčíková, M. Kotora, P. Kočovský, Chem. Eur. J. 2011, 17, 7162.
165. A. V. Malkov, L. Dufková, L. Farrugia, P. Kočovský, Angew. Chem. 2003, 115, 3802
166. Angew. Chem. Int. Ed. 2003, 42, 3674
167. A. V. Malkov, M. Bell, P. Ramírez-Lõpez, L. Biedermannová, L. Rulíšek, L. Dufková, M. Kotora, F. Zhu, P. Kočovský, J. Am. Chem. Soc. 2008, 130, 5341.
168. A. Massa, A. V. Malkov, P. Kočovský, A. Scettri, Tetrahedron Lett. 2003, 44, 7179. For an overview on catalysis by chiral phosphoramides, see
169. S. E. Denmark, J. Fu, Chem. Rev. 2003, 103, 2763.
170. A. V. Malkov, P. Kočovský, Curr. Org. Chem. 2003, 7, 1737
171. P. Kočovský, A. V. Malkov, Izv. Akad. Nauk Ser. Khim. 2004, 1733
172. Russian Chem. Bull. Int. Ed. 2004, 59, 1806
173. A. V. Malkov, P. Kočovský, Eur. J. Org. Chem. 2007, 29
174. "Chiral Lewis Bases as Catalysts": P. Kočovský, A. V. Malkov, in Enantioselective Organocatalysis-Reactions and Experimental Procedures (Ed.:, P. I. Dalko,), Wiley-VCH, Weinheim, 2007, p. 255
175. P. Kočovský, A. V. Malkov, Pure Appl. Chem. 2008, 80, 953.
176. For the method, see:, K. Iseki, Y. Kuroki, M. Takahashi, S. Kishimoto, Y. Kobayashi, Tetrahedron 1997, 53, 3513.
177. For the method, see:, J. Tsuji, M. Hara, K. Ohno, Tetrahedron 1974, 30, 2143.
178. A. V. Malkov, M. A. Kabeshov, M. Barłõg, P. Kočovský, Chem. Eur. J. 2009, 15, 1570.
179. R. W. Bates, K. Sa-Ei, Org. Lett. 2002, 4, 4225
180. R. W. Bates, J. Boonsombat, Org. Biomol. Chem. 2005, 3, 520
181. R. W. Bates, J. Boonsombat, Y. Lu, J. A. Nemeth, K. Sa-Ei, P. Song, M. P. Cai, P. B. Cranwell, S. Winbush, Pure Appl. Chem. 2008, 80, 681. For a related, gold(I)-catalyzed neighboring-group participation in the ring-closing functionalization of Boc-protected ynamines, see
182. A. S. K. Hashmi, R. Salathé, W. Frey, Synlett 2007, 1763.
183. R. W. Bates, J. A. Nemeth, R. H. Snell, Synthesis 2008, 1033
184. R. W. Bates, R. H. Snell, S. Winbush, Synlett 2008, 1042
185. R. W. Bates, Y. N. Lu, J. Org. Chem. 2009, 74, 9460
186. R. W. Bates, C. J. Lim, Synlett 2010, 866
187. R. W. Bates, Y. N. Lu, Org. Lett. 2010, 12, 3938.
188. B. Janza, A. Studer, J. Org. Chem. 2005, 70, 6991
189. K. G. Dongol, B. Y. Tay, K. Xiang, Synth. Commun. 2006, 36, 1247
190. R. W. Bates, P. Song, Synthesis 2009, 655.
191. Retention by using 3,3'-di-tert-butyloxaziridine as the reagent:, I. C. Choong, J. A. Ellman, J. Org. Chem. 1999, 64, 6528.
192. O. F. Foot, D. W. Knight, Chem. Commun. 2000, 975. For constructing the N-N bond with the same reagent, see
193. J. Vidal, J.-C. Hannachi, G. Hourdin, J.-C. Mulatier, A. Collet, Tetrahedron Lett. 1998, 39, 8845.
194. O. Mitsunobu, Y. Yamada, Bull. Chem. Soc. Japan 1967, 40, 2380
195. O. Mitsunobu, Synthesis 1981, 1
196. D. L. Hughes, Org. React. 1992, 42, 335.
197. R. van Asselt, F. C. G. Gielens, R. E. Rülke, K. Vrieze, C. J. Elsevier, J. Am. Chem. Soc. 1994, 116, 977. For other stereodirecting effects of carbamate groups and discussion, see
198. P. Kočovský, Tetrahedron Lett. 1988, 29, 2475
199. P. Kočovský, I. Starý, J. Org. Chem. 1990, 55, 3236. For other coordinating groups, see Ref. [20].
200. 2/dppe in refluxing toluene, Dongol also assumed the syn-addition but with no experimental evidence:, K. G. Dongol, B. Y. Tay, Tetrahedron Lett. 2006, 47, 927.
201. For the original method, see:, S. Cicchi, A. Goti, A. Brandi, A. Guarna, F. De Sarlo, Tetrahedron Lett. 1990, 31, 3351.
202. H. Kuno, M. Shibagaki, K. Takahashi, I. Honda, H. Matsushita, Chem. Lett. 1992, 571
203. J. Fujita, S. Watanabe, K. Suga, Y. Higuchi, T. Sotoguchi, J. Org. Chem. 1984, 49, 1975
204. C. Bonini, P. Pucci, R. Racioppi, L. Viggiani, Tetrahedron: Asymmetry 1992, 3, 29
205. D. Berkeš, A. Kolarovič, R. Manduch, P. Baran, F. Považanec, Tetrahedron: Asymmetry 2005, 16, 1927
206. J. D. White, N. J. Green, F. F. Fleming, Tetrahedron Lett. 1993, 34, 3515
207. A. Makita, T. Nihira, Y. Yamada, Tetrahedron Lett. 1987, 28, 805. For lactonization with DBU, see
208. J. J. Gaudino, C. S. Wilcox, Carbohydr. Res. 1990, 206, 233
209. Y. Yoshida, Y. Ukaji, S. Fujinami, K. Inomata, Chem. Lett. 1998, 1023
210. Z. Yang, W. Zhou, Tetrahedron 1995, 51, 1429.
211. Protected hydrazines, obtained from 4 via the Mitsunobu reaction with dialkyl diazodicarboxylate (for the method, see:, M. J. Di Grandi, J. W. Tilley, Tetrahedron Lett. 1996, 37, 4327), undergo analogous, ring-closing amidocarbonylation to produce the pyrrazolidine analogues of isoxazolidines 16; details of this new procedure will be disclosed in due course.
212. For the Pd-catalyzed cyclization of N-tosyl carbamates in the absence of CO, see:, F. Nahra, F. Liron, G. Prestat, C. Mealli, A. Messaoudi, G. Poli, Chem. Eur. J. 2009, 15, 11078 and references cited therein. For correction, see
213. F. Nahra, F. Liron, G. Prestat, C. Mealli, A. Messaoudi, G. Poli, Chem. Eur. J. 2010, 16, 1414. In a similar way, our carbamate 15 undergoes an analogous cyclization in the absence of CO, giving rise to the corresponding oxazolidine with a pendant vinyl group; details will be communicated in due course.
214. X. Ding, K. Taniguchi, Y. Hamamoto, K. Sada, S. Fujinami, Y. Ukaji, K. Inomata, Bull. Chem. Soc. Jpn. 2006, 79, 1059
215. Y. Ukaji, K. Taniguchi, I. Sada, Chem. Lett. 1997, 547. For the synthesis of negamycin via nitrone addition, see
216. H. Iida, K. Kasahara, C. Kibayashi, J. Am. Chem. Soc. 1986, 108, 4647
217. D. Socha, M. Jurczak, M. Chmielewski, Tetrahedron Lett. 1995, 36, 135. For the nitrone approach to monomorine, see
218. M. Ito, C. Kibayashi, Tetrahedron Lett. 1990, 31, 5065
219. M. Ito, C. Kibayashi, Tettrahedron 1991, 47, 9329
220. N. Morita, K. Fukui, J. Irikuchi, H. Sato, Y. Takano, I. Okamoto, H. Ishibashi, O. Tamura, J. Org. Chem. 2008, 73, 7146.
221. For the construction of isoxazolidines via the organocatalyzed intramolecular addition of an N-Boc-protected hydroxylamine moiety across a conjugated double bond, see:, Y. K. Chen, M. Yoshida, D. W. C. MacMillan, J. Am. Chem. Soc. 2006, 128, 9328.
222. J. A. Dale, D. L. Dull, H. S. Mosher, J. Org. Chem. 1969, 34, 2543
223. J. A. Dale, H. S. Mosher, J. Am. Chem. Soc. 1973, 95, 512
224. H. Iwagami M. Yatagai, M. Nakazawa, H, Orita, Y. Honda, T. Ohnuki, T. Yukawa, Bull. Chem. Soc. Jpn. 1991, 64, 175
225. J. Nokami, M. Ohga, H. Nakamoto, T. Matsubara, I. Hussain, K. Kataoka, J. Am. Chem. Soc. 2001, 123, 9168.
226. R. H. Blessing, J. Appl. Crystallogr. 1989, 22, 396.
227. A. Altomare, G. Cascarano, C. Giacovazzo, A. Guagliardi, M. C. Burla, G. Polidori, M. Camalli, J. Appl. Crystallogr. 1994, 27, 435.
228. L. Palatinus, G. Chapuis, J. Appl. Crystallogr. 2007, 40, 786.
229. G. M. Sheldrick, Acta Crystallogr. Sect. A 2008, 64, 112.
230. For comparison, see Ref. [44] and the following:, T. Ishikawa, M. Kawakami, M. Fukui, A. Yamashita, J. Urano, S. Saito, J. Am. Chem. Soc. 2001, 123, 7734.