Allylic protecting groups and their use in a complex environment Part II: Allylic protecting groups and their removal through catalytic palladium π-allyl methodology

Tetrahedron

Volumn 54, Issue 13, 1998, Pages 2967-3042

  Guibé, François ^a  

^a UNIVERSITÉ PARIS SUD   (France)

Author keywords

[No Author keywords available]

Indexed keywords

ALLYL COMPOUND; PALLADIUM;

ALKYLATION; CATALYSIS; COMPLEX FORMATION; PRIORITY JOURNAL; REVIEW; SYNTHESIS;

EID: 0032568384     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(97)10383-0     Document Type: Review

References (267)

1. 1. Part I : Tetrahedron Report Number 428, Tetrahedron 1997, 53, 13509-13555.
2. 2. For reviews or books partially concerned with this topic, see: (a) Kunz, H. Ang. Chem. Int. Ed. Engl. 1987, 26, 294-308;
3. (b) Salomon, C. J.; Mala, E. G.; Mascareti, O. A. Tetrahedron 1993, 49, 3691-3748;
4. (c) Schelhaas, M; Waldmann, H. Ang. Chem. Int. Ed. Engl. 1996, 32, 2056-2083;
5. (d) Kocienski, P. J. Protecting Groups, Georg Thieme Verlag, Stuttgart, New York, 1994;
6. (e) Greene, T. W.; Wuts, P. G. M. Protective Groups in Organic Synthesis, 2nd Ed., John Wiley, New York, 1991;
7. (f) Tsuji, J.; Mandaï, T. Synthesis, 1996, 1-24
8. 3. Selected reviews: (a) Trost, B. M. Acc. Chem. Res. 1980, 13, 385-393;
9. (b)Tsuji, J. Organic Synthesis with Palladium Compounds, Springer Verlag, Berlin, 1980, pp. 37-50 and 125-134;
10. (c) Trost, B. M.; Verhoeven, T. R. in Comprehensive Organometallic Chemistry, G. Wilkinson Ed., Pergamon Press, Oxford, 1982, vol. 8, pp. 802-854;
11. (d) Godleski, S. A. in Comprehensive Organic Synthesis, B. M. Trost Ed., Pergamon Press, Oxford, 1991, Vol. 4, pp. 585-661;
12. (e) Frost, G. C.; Howarth, J.; Williams, J. M. J. Tetrahedron: Asymmetry, 1992,5, 1089-1122;
13. (f) Tsuji J. Pure Appl. Chem. 1986, 58, 869-878 and 1982, 54, 197-206;
14. (f) Tsuji J. Pure Appl. Chem. 1986, 58, 869-878 and 1982, 54, 197-206;
15. (g) Tsuji, J. Tetrahedron 1986, 42, 4361-4401;
16. (h) Trost, B. M.; Van Vranken, D. L. Chem. Rev. 1996, 96, 395-422.
17. 4. (a) Amatore, C; Pflüger, F. Organometallics, 1990, 9, 2276-2282;
18. (b) Amatore, C.; Azzabi, M.; Jutand, A. J. Am. Chem. Soc. 1991, 113, 8375-8384;
19. (c) Amatore, C.; Carré, E.; Jutand, A.; M'Barki, M. A.; Meyer, G. Organometallics, 1995, 14, 5605-5614.
20. 5. The reaction studied by the authors involve oxidative addition to phenyl iodide and not to allylic electrophiles. It is however our belief that the conclusions drawn by these authors, if not strictly transposable to π-allyl palladium chemistry, remain highly instructive.
21. 6. Amatore, C.; Jutand, A.; Khalil, F.; M'Barki, M. A.; Mottier, L. Organometallics, 1993, 12, 3168-3178.
22. 7. See for instance Trost, B. M.; Lee, C. B.; Weiss, J. M. J. Am. Chem. Soc. 1995, 117, 7247-7248.
23. 8. Amatore C.; Jutand, A.; Suarez, A. J. Am. Chem. Soc. 1993, 115, 9531-9541 and refs therein.
24. 9. (a) Amatore, C.; Jutand, A.; M'Barki, M. A. Organometallics, 1992, 11, 3009-3013;
25. (b) Amatore, C; Carré, E.; Jutand, A.; M'Barki, M. A. Organometallics, 1995, 14, 1818-1826.
26. 10. Stary, I.; Kocovsky, P. J. Am. Chem. Soc. 1989, 111, 4981-4982.
27. 11. Collman, J. P.; Hegedus, L. S.; Norton, J. R., Finke, R. G. Principles and Applications of Organotransition Metal Chemistry, University Science Book, Mill Valley (USA) 1987
28. 12. see for instance Godleski, S. A.; Gundlach, K. B.; Ho, H. Y. Keinan; E.; Frolow, F. Organometallics 1984, 3, 21-28.
29. 13. Fiaud, J.-C.; Legros, J.-Y. J. Org. Chem. 1987, 52, 1907-1911.
30. 14. Stary, I.; Zajicek, J.; Kocovsky, P. Tetrahedron 1992, 48, 7229-7250 and refs therein.
31. 15. Sennyey, G.; Barcelo, G.; Senet, J.-P. Tetrahedron Lett. 1987, 26, 5809-5810.
32. 16. Takeda, K.; Akiyama, A.; Nakamura, H.; Takizawa, S.-I.; Mizuno, Y.; Takayanagi, H.; Harigaya, H. Synthesis, 1994, 1063-1066.
33. 17. Hayakawa, Y.; Wakabayashi, S.; Kato, H.; Noyori, R. J. Am. Chem. Soc. 1990, 112, 1691-1696.
34. 18. Harada, T.; Yamada, H.; Tsukamoto, H.; Takahashi, T. J. Carbohydr. Chem. 1995, 14, 165-170.
35. 19. Matray, T. J.; Greenberg, M. M. J. Am. Chem. Soc. 1994, 116, 6931-6932.
36. 20. Takeda K. Tetrahedron Lett. 1995, 36, 113.
37. 21. Minami, I.; Ohashi, Y.; Shimizu, I.; Tsuji, J. Tetrahedron Lett. 1985, 26, 2449-2452.
38. 22. Merzouk, A.; Guibé, F.; Loffet, A. Tetrahedron Lett. 1992, 33, 477-480.
39. 23. unpublished results from our laboratory.
40. 24. Genêt, J.-P.; Blart, E.; Savignac, M.; Lemeune, S.; Lemaire-Audoire, S.; Bernard, J.-M. Synlett 1993, 680-682.
41. 25. Jeffrey, P. D.; McCombie, S. W. J. Org. Chem. 1982, 47, 587-590.
42. 26. Jungheim, L. N.; Sigmund, S.K.; Fisher, J. W. Tetrahedron Lett. 1987, 28, 285-288.
43. 27. Ruediger, E. H.; Solomon, C. J. Org. Chem. 1991, 56, 3183-3187.
44. 28. Paquette, L.,A.; McDonald, D.; Anderson, L. G. J. Am. Chem. Soc. 112, 1990, 9292-9299.
45. 29. Martin, S. F.; Campbell C. L. J. Org. Chem. 1988, 53, 3184-3190.
46. 30. Christ, W. J.; McGuiness, P. D.; Asano, O.; Wang, Y.; Mullarkey, M. A.; Perez, M.; Hawkins, L.D.; Blythe, T. A.; Bubuc, G. R.; Robidoux, A. L. J. Am. Chem. Soc. 1994, 116, 3637-3638.
47. 31. allyl carbonates: (a) ref 3g;
48. (b) Tsuji, J.; Minami, I. Acc. Chem. Res. 1987, 20, 140-145; allyl phosphates:
49. (c) Tanigawa, Y.; Nishimura, K.; Kawasaki, A.; Murahashi, S.-I. Tetrahedron Lett. 1982, 23, 5549-5552.
50. 32. Jasys, V. J.; Kelbaugh, P. R.; Nason, D. M.; Phillips, D.; Rosnach, K. J.; Forman, J.T.; Saccomano, N. A.; Stroh, J. G.; Volkmann, R. A. J. Org. Chem. 1992, 57, 1814-1820.
51. 33. Kolasa, T.; Miller, M. J. J. Org. Chem. 1990, 55, 1711-1721.
52. 34. Nakayama, K.; Uoto, K.; Higashi, K.; Soga, T.; Kusama, T. Chem. Pharm. Bull. 1992, 40, 1718-1720.
53. 35. Kinoshita, H.; Inomata, K.; Kameda, T.; Kotake, H. Chem. lett. 1985, 515-518.
54. 36. Blankemeyer-Menge, B.; Frank, R. Tetrahedron Lett. 1988, 29, 5871-5874.
55. 37. Handa, B. K.; Keech, E. Int. J. Peptide Protein Res. 1992, 40, 66-71.
56. 38. Trost, B., M.; Ito, N.; Greenspoon, P. D. Tetrahedron Lett. 1993, 34, 1421-1424.
57. 39. Flack, S. S., Kilburn, J. D. Tetrahedron Lett. 1995, 36, 3409-3412.
58. 40. Kunz, H.; Waldmann, H. Ang. Chem. Int. Ed. Engl. 1984, 23, 71-72.
59. 41. Schmidt, U.; Riedl, B. J. Chem. Soc. Chem. Commun. 1992, 1186-1187.
60. 42. Genêt, J.-P.; Blart, E.; Savignac, M.; Lemeune, S.; Paris, J.-M. Tetrahedron Lett. 1993, 34, 4189-4192.
61. 43. Genêt, J.-P.; Blart, E.; Savignac, M.; Lemeune, S.; Lemaire-Audoire, S.; Paris, J.-M.; Bernard, J.-M. Tetrahedron 1994, 50, 497-503.
62. 44. Lemaire-Audoire, S.; Savignac, M.; Blart, E.; Pourcelot, G.; Genêt, J.-P; Bernard, J.-M. Tetrahedron Lett. 1994, 35, 8783-8786.
63. 45. Kunz, H.; Waldmann, H.; Unverzagt, C. Int. J. Peptide Protein Res. 1985, 26, 493-497
64. 46. Bardaji, E.; Torres, J. L.; Xaus, N., Clapes, P.; Jorba, X.; de la Torre, B. G.; Valencia, G. Synthesis 1990, 531-532.
65. 47. Jouin, P.; Poncet, J.; Dufour, M.-N.; Pantaloni, A.; Castro, B. J. Org. Chem. 1989, 54, 617-627.
66. 48. Schmidt, U.; Mundinger, K.; Mangold, R.; Lieberknecht, A. J. Chem. Soc. Chem. Commun. 1990, 1216-1219.
67. 49. Kunz, H.; Waldmann, H. Ang. Chem. Int. Ed. Engl. 1985, 24, 883-885.
68. 50. Kunz, H.; Waldmann, H. J. Chem. Soc. Chem. Commun. 1985, 638-640.
69. 51. Friedrich-Bochnitschek, S.; Waldmann, H.; Kunz, H. J. Org. Chem. 1989, 54, 751-756.
70. 52. Kunz, H.; März, J. Synlett 1992, 589-590 and 591-593.
71. 53. Dommerholt, F. J.; ThijS, L.; Zwanenburg, B. Tetrahedron Lett. 1991, 32, 1499-1502.
72. 54. Hoffmann, R. W.; Ditrich, K. Liebigs Ann. Chem. 1990, 23-29.
73. 55. Okamoto, S.; Ono, N.; Tani, K., Yoshida, Y.; Sato, F. J. Chem. Soc. Chem. Commun. 1994, 279-280.
74. 56. Alsina, J.; Rabanal, F.; Giralt, E.; Albericio, F. Tetrahedron Lett. 1994, 35, 9633-9636.
75. 57. Kates, S. A.; Daniels, S. B.; Albericio, F. Analytical Biochemistry 1993, 212, 303-310.
76. 58. Kates, S. A.; Solé, N. A.; Johnson, C. R.; Hudson, D.; Barany, G.; Albericio, F. Tetrahedron Lett. 1993, 34, 1549-1552.
77. 59. Deziel, R. Tetrahedron Lett. 1987, 28, 4371-72.
78. 60. Baldwin, J. E.; Moloney, M. G.; North, M. Tetrahedron 1989, 45, 6319-6330.
79. 61. M. S. Stanley J. Org. Chem. 1992, 57, 6421-6430.
80. 62. Dolence, E. K.; Miller, M. J. J. Org. Chem. 1991, 56, 492-499;
81. 63. Lotz, B. T.; Miller, M. J. J. Org. Chem. 1993, 58, 618-625.
82. 64. Hayakawa, Y.; Uchiyama, M.; Kato, H.; Noyori, R. Tetrahedron Lett. 1985, 26, 6505-6508.
83. 65. Hayakawa, Y.; Hirose, M.; Noyori, R. J. Org. Chem. 1993, 58, 5551-5555.
84. 66. Sigismondi, S.; Sinou, D. J. Chem. Res. S 1996, 46-47.
85. 67. Mastalerz, H.; Vinet, V. J. Chem. Soc. Chem. Commun. 1987, 1283-1284.
86. 68. von dem Bruch, K; Kunz, H. Angew. Chem. Int. Edit. Engl. 1990, 29, 1457-1459.
87. 69. Ciommer, M.; Kunz, H. Synlett 1991, 593-595
88. 70. Llyod-Williams, P.; Merzouk, A.; Guibé, F.; Albericio, F.; Giralt, E. Tetrahedron Lett. 1994, 35, 4437-4440.
89. 71. Bloomberg, G. B.; Askin, D.; Gargaro, A. R.; Tanner, M. J. A. Tetrahedron Lett. 1993, 34, 4709-4712.
90. 72. Kates, S. A.; de la Torre, B. G.; Eritja, R.; Albericio, F. Tetrahedron Lett. 1994, 35, 1033-1034.
91. 73. Vetter, D.; Tumelty, D.; Singh, S. K.; Gallop, M. A. Angew. Chem. Int. Ed. Engl. 1995, 34, 60-63.
92. 74. Kates, S. A.; Daniels, S. B.; Solé, N. A.; Barany, G.; Albericio, F. Proceedings of the 13th American Peptide Symposium, Hodges, R. S.; Smith, J. A. Eds, Escom, Leiden, 1994, pp 113-115.
93. 75. Kunz, H.; Unverzagt, C. Angew. Chem. Int. Ed. Engl. 1984, 23, 436-437.
94. 76. Kunz, H.; März, J. Angew. Chem. Int. Ed. Engl. 1988, 27, 1375-1377.
95. 77. Note however recent evidence that palladium-assisted allylic carbon-carbon bond cleavage may occur, especially in the case of quaternary allylic β-dicarbonyl compunds, as testified for instance in the isomerization reaction of eq. i : Nilsson, Y. I. M.; Andersson, P. G.; Bäckvall, J.-E. J. Am. Chem. Soc. 1993, 115, 6609-6613. (formula presented)
96. 78. A similar mechanism applies to the deprotection of allyl carbonates.
97. 79. unpublished observations from our laboratory.
98. 80. Halpern, B.; James, L. B. Aust. J. Chem. 1964, 17, 1282-1287.
99. 81. Kunz, H. Angew. Chem. Int. Ed. Engl. 1987, 26, 294-308 (review).
100. 82. Kunz, H.; Unverzagt, C. Angew. Chem. Int. Ed. Engl. 1988, 27, 1697-1699.
101. 83. Braun, P.; Waldmann, H.; Vogt, W.; Kunz, H. Synlett 1990, 105-106.
102. 84. Smith, A. B., Guzman, M. C.; Sprengeler, P. A.; Keenan, T.P.; Holcomb, R. C.; Wood, J. L.; Caroll, P. J.; Hirschmann, R. J. Am. Chem. Soc.1994, 116, 9947-9962.
103. 85. Smith, A. B.; Holcomb, R. C.; Guzman, M. C.; Keenan, T. P.; Sprengeler, P. A.; Hirschmann, R.T. Tetrahedron Lett. 1993, 34, 63-66.
104. 86. Arnoult, J. C.; Landier, F.; Pasquet, M. J. Tetrahedron Lett. 1992, 33, 7133-7136.
105. 87. Teshima, T.; Nakajima, K.; Takahashi, M.; Shiba, T. Tetrahedron Lett. 1992, 33, 363-366.
106. 88. Boullanger, P.; Descotes, G. Tetrahedron Lett. 1986, 27, 2599-2602.
107. 89. Schultz, M.; Kunz, H. Tetrahedron Lett. 1992, 33, 5319-5322.
108. 90. Schultz, M.; Hermann, P.; Kunz, H. Synlett 1992, 37-38.
109. 91. Boullanger, P.; Banoub, J.; Descotes, G. Can. J. Chem. 1987, 65, 1343-1348.
110. 92. Lafont, D.; Boullanger, P.; Banoub, J.; Descotes G. Can. J. Chem. 1990, 68, 828-835.
111. 93. Ishiguro, M.; Iwata, H.; Nakatsuka, T.; Nakajima, M.; Yamada, Y.; Doi, J. Eur. Pat. Appl. EP 410,727; Chemical Abstracts 1991, 115: 28982p.
112. 94. Wipf, P.; Kim, H. J. Org. Chem. 1993, 58, 5592-5594.
113. 95. Kunz, H.; Waldmann, H.; Unverzagt, C. Int. J. Peptide Protein Res. 1985, 26, 493-497.
114. 96. Sunakawa, J.; Takeuchi, Y.; Kitamura, Y. Jpn. Kokai Tokkyo Koho JP 01 75,488 [89 75,488]; Chemical Abstracts 1989, 111: 173900g
115. 97. Ni(0) catalysed allylic substitution reactions : (a) Kobayashi, Y.; Ikedo, E. J. Chem. Soc. Chem. Commun. 1994, 1789-1790;
116. (b) Bricout, H.; Carpentier, J. F.; Mortreux, A. J. Chem. Soc. Chem. Commun. 1994, 1863-1864;
117. (c) Bricout, H.; Carpentier, J. F.; Mortreux, A. Tetrahedron Lett. 1996, 37, 6105-6108.
118. 98. Durette, P. L.; Baker, F.; Barker, P. L.; Boger, J.; Bondy, S. S.; Milton, L. H.; Lanza, T. J.; Pessolano, A. A.; Caldwell, C. G. Tetrahedron Lett. 1990, 31, 1237-1240.
119. 99. Borchard, A.; Still, W. C. J. Am. Chem. Soc. 1994, 116, 7467-7468.
120. 100. Loffet, A.; Zhang, H. X. personal communication.
121. 101. Garro-Hélion, F.; Merzouk, A.; Guibé, F. J. Org. Chem. 1993, 58, 6109-6113.
122. 102. (a) Lemaire-Audoire, S.; Savignac, M.; Genêt, J.-P.; Bernard, J. M. Tetrahedron Lett. 1995, 36, 1267-1270;
123. (b) Lemaire-Audoire, S.; Savignac, M.; Dupuis, C.; Genêt, J.-P. Bull. Soc. Chim. Fr. 1995, 132, 1157-1166.
124. 103. For recent utilizations of this system, see: (a) Zhang, D.; Liebeskind, L. S. J. Org. Chem. 1996, 61, 2594-2595;
125. (b) Bailey, W. F.; Jiang, X.-L. J. Org. Chem. 1996, 61, 2596-2597.
126. 104. Merzouk, A. Doctorat en Sciences, Université Paris-Sud, November 16, 1993.
127. 105. Shapiro, G.; Buechler, D. Tetrahedron Lett. 1994, 35, 5421-5424.
128. 106. Corriu, R. J. P.; Colin Young, J. Hypervalent Silicon Compounds in The Chemistry of Organic Silicon Compounds, Part II, S. Patai, Z. Rappoport, John Wiley, 1989, pp 1241-1288.
129. 107. Palladium catalysed azidation of allyl esters with trimethylsilyl azide in the absence of fluoride cocatalyst requires heating at 52°C: Safi, M.; Fahrang, R.; Sinou, D. Tetrahedron Lett. 1990, 31, 527-530.
130. 108. Review: ref. 2f
131. 4: (a) Keinan, E.; Roth, Z. J. Org. Chem. 1983, 48, 1769-1772;
132. 2H:
133. (c) Mandai, T.; Matsumoto, T.; Kawada, M.; Tsuji, J. J. Org. Chem. 1992, 57, 1326-1327.
134. (d): Mandai, T.; Matsumoto, T.; Kawada, M.; Tsuji, J. Tetrahedron 1994, 50, 475-486.
135. 110. Hey, H.; Arpe, H. J. Angew. Chem. Int. Ed. Engl. 1973, 12, 928-929.
136. 111. Tsuji, J.; Yamakawa, T. Tetrahedron Lett. 1979, 613-616.
137. 112. Kock, T.; Hesse, M. Synthesis 1992, 931-932.
138. 113. Corey, E. J.; Reichard, G. A. J. Am. Chem. Soc. 1992, 114, 10677-10678.
139. 114. Ono, N.; Tsuboi, M.; Okamoto, S.; Tanami, T.; Sato, F. Chem. Lett. 1992, 2095-2098.
140. 115. Chida, N.; Takeoka, J.; Tsutsumi, N.; Ogawa, S. J. Chem. Soc. Chem. Commun. 1995, 793-794.
141. 116. Guibé, F.; Saint M'Leux, Y. Tetrahedron Lett. 1981, 22, 3591-3594.
142. 117. Hayakawa, Y.; Kato, H.; Uchiyama, M., Kajino, H.; Noyori, R. J. Org. Chem. 1986, 51, 2402-2404.
143. 118. Romo, D.; Meyer, S. D.; Johnson, D. D.; Schreiber, S. L. J. Am. Chem. Soc. 1993, 115, 7906-7907.
144. 119. Matray, T. J.; Greenberg, M.M. J. Am. Chem. Soc. 1994, 116, 6931-6932.
145. 120. ref. 18
146. 121. Hayakawa, Y.; Wakabayashi, S.; Kato, H., Noyori, R. J. Am. Chem. Soc. 1990, 112, 1691-1696.
147. 122. Greenberg, M. M.; Gilmore, T. L. J. Org. Chem. 1994, 59, 746-753.
148. 123. Yamada, T.; Goto, K.; Mitsuda, Y.; Tsuji, J. Tetrahedron Lett. 1987, 28, 4557-4560.
149. 124. Hayakawa, H.; Uchiyama, M.; Kato, H., Noyori, R. Tetrahedron Lett. 1985, 26, 6505-6508.
150. 125. Hayakawa, Y.; Wakabayashi, S.; Nobori, T.; Noyori, R. Tetrahedron Lett. 1987, 28, 2259-2262.
151. 126. Hayakawa, Y.; Nobori, T.; Noyori, R.; Imai, J. Tetrahedron Lett. 1987, 28, 2623-2626.
152. 127. Banwarth, W.; Kung, E. Tetrahedron Lett. 1989, 30, 4219-4222.
153. 128. Tsuji, J.; Nisar, M.; Shimizu, I. J. Org. Chem. 1985, 50, 3416-3417.
154. 129. Nokami, J.; Okhura, M.; Dan-Oh, Y.; Sakamoto, Y. Tetrahedron Lett. 1991, 32, 2409-2412.
155. 130. Murayama, T.; Yoshida, A.; Kobayashi, T.; Miura, T. Tetrahedron Lett. 1994, 35, 2271-2274.
156. 131. Hanessian, S.; Rozema, M. J. J. Am. Chem. Soc. 1996, 118, 9884-9891.
157. 132. Oshima, M.; Shimizu, I.; Yamamoto, A.; Ozawa, F. Organometallics, 1991, 10, 1221-1223.
158. 133. A 6-electron 6-center cyclic process may also be envisioned (eq. below). For a recent discussion of electrocyclic processes in π-allyl palladium chemistry, see: Keinan, E.; Kumar, S.; Danjur, V.; Vaya, J. J. Am. Chem. Soc. 1994, 116, 11151-11152. (formula presented)
159. 134. Rutjes, F. P. J. T.; Paz, M. M.; Hiemstra, H.; Speckamp, W. N. Tetrahedron Lett. 1991, 32, 6629-6632.
160. 2H). If so, side formation of allylamine should be avoidable by adding the Alloc derivative to a preheated solution of scavengers and catalyst.
161. 136. Review : Guibé, F. Main Group Metal Chemistry, 1989, 13, 437-446.
162. 137. (a) Keinan, E.; Gleize, P. A. Tetrahedron Lett. 1982, 477-480;
163. (b) Keinan, E.; Greenspon, N.; J. Org. Chem. 1983, 48, 3545-3548.
164. 138. (a) Four, P.; Guibé, F. Tetrahedron Lett. 1982, 23, 1825-1828;
165. (b) Yang, T. X.; Four, P.; Guibé, F.; Balavoine, G. Nouv. J. Chim. 1984, 5, 611-614.
166. 139. Ichinose. Y.; Oda, H.; Oshima, K.; Utimoto, K. Bull. Chem. Soc. Jpn 1987, 60, 3468-3470.
167. 140. Zhang, H. X.; Guibé, F.; Balavoine, G. Tetrahedron Lett. 1988, 29, 619-622.
168. 141. Zhang, H. X.; Guibé, F.; Balavoine, G. J. Org. Chem. 1990, 55, 1857-1867.
169. 142. Four, P.; Guibé, F. J. Org. Chem. 1981, 46, 4439-4445
170. 143. Guibé, F.; Zigna, A.-M.; Balavoine, G. J. Organomet. Chem. 1986, 306, 257-265. Guibé, F.; Yang, T. X., Balavoine, G. J. Organomet. Chem. 1986, 506, 267-272.
171. 143. Guibé, F.; Zigna, A.-M.; Balavoine, G. J. Organomet. Chem. 1986, 306, 257-265. Guibé, F.; Yang, T. X., Balavoine, G. J. Organomet. Chem. 1986, 506, 267-272.
172. 144. Dangles, O.; Guibé, F.; Balavoine, G., Lavielle, S.; Marquet, A. J. Org. Chem. 1987, 52, 4984-4995.
173. 145. Tanaka, M.; Okita, M.; Yamatsu, I. Carbohydr. Res. 1993, 241, 81-88.
174. 146. Zhang, H. X.; Guibé, F.; Balavoine, G. Tetrahedron Lett. 1988, 29, 623-626.
175. 147. Neumann, W. P. Synthesis 1987, 665-683 (review).
176. 148. Leibner, J. E.; Jacobus;, J. J. Org. Chem. 1979, 44, 449-450.
177. 149. Yin, H.; Franck, R. W.; Chen, S. L.; Quigley, G. J.; Todaro, L. J. Org. Chem. 1992, 57, 644-651.
178. 150. Evans, D. A.; Ellman, J. A.; de Vries, K. M. J. Am. Chem. Soc. 1989, 111, 8912-8914.
179. 151. Boos, E. C.; Bernabé, P.; Hiemstra, H.; Speckamp, W. N.; Kaptein, B.; Boesten, W. J. Tetrahedron Lett. 1991, 32, 6633-6636.
180. 152. Boos, E. C.; Bernabé, P.; Hiemstra, H.; Speckamp, W. N.; Kaptein, B.; Boesten, W. J. J. Org. Chem. 1995, 60, 1733-1740.
181. 153. Guibé, F.; Yang, T. X.; Zigna, A. M.; Balavoine, G. Tetrahedron Lett. 1985, 26, 3559-3562.
182. 154. Coates, R. M.; Sandefur, L. O.; Smillie, R. D. J. Am. Chem. Soc. 1975, 97, 1619-1621.
183. 155. Guibé, F.; Yang, T. X.; Balavoine, G. Nouv. J. Chim. 1986, 10, 697-699.
184. 156. Hutchins, R. O.; Learn, K.; Fulton, R. P. Tetahedron Lett. 1980, 21, 27-30.
185. 157. Beugelmans, R.; Bourdet, S.; Bigot, A.; Zhu, J. Tetrahedron Lett. 1994, 35, 4349-4350.
186. 158. Beugelmans, R.; Neuville, L.; Bois-Choussy, M.; Chastanet, J.; Zhu, J. Tetrahedron Lett. 1995, 36, 3129-3132.
187. 159. alkoxy-or acyloxyborates compounds: see Steinberg, H. Organoboron Chemistry, John Wiley, 1964, pp 775-792.
188. 160. Keinan, E.; Greenspoon, N. Isr. J. Chem. 1984, 24, 82-87.
189. 161. (a) Dessolin, M.; Guillerez, M.-G.; Thieriet, N.; Guibé, F.; Loffet, A. Tetrahedron Lett. 1995, 32, 5741-5744;
190. (b) Thieriet, N.; Guibé, F., Loffet, A. In Peptides 1996 Proceedings of the 24th European Peptide Symposium; Ramage, R.; Epton, R., Ed.; Mayflower Scientific Ltd., Kingswinford, 1977, in press.
191. 162. Sakaitani, M.; Ohfune, Y. J. Org. Chem. 1990, 55, 870-876.
192. 163. Sakaitani, M.; Hori, K.; Ohfune, Y. Tetrahedron Lett. 1988, 29, 2983-2984.
193. 164. Lacombe, J. M.; Andriamanampisoa, F.; Pavia, A. A. Int. J. Peptide Protein Res. 1990, 36, 275-280.
194. 165. Maffre-Lafon, D.; Escale, R.; Dumy, P.; Vidal, J.-P.; Girard, J.-P. Tetrahedron Lett. 1994, 35, 4097-4098.
195. 166. (a) Tuchscherer, G.; Mutter, M. J. Peptide Science, 1995, 1, 3-10;
196. (b) Ernest, I.; Kalvoda, T.; Sigel, C.; Rihs, G.; Fritz, H.; Blommers, M. J. J.; Rachsdorf, F.; Francotte, E.; Mutter, M. Helv. Chim. Acta 1993, 76, 1539-1563;
197. (c) Mutter, M.; Vuilleumier, S. Angew. Chem. Int. Ed. Engl. 1989, 28, 535-554.
198. 167. (a) Dumy, P.; Eggleston, I. M.; Cervigni, S.; Sila, U.; Sun, X.; Mutter, M. Tetrahedron Lett. 1995, 36, 1255-1258;
199. (b) see also: Sila, U.; Mutter, M. J. Mol. Recognition 1995, 8, 29-34.
200. 168. Bycroft, B. W.; Chan, W. C.; Chhabra, S. R.; Hone, N. D. J. Chem. Soc. Chem. Commun. 1993, 778-779.
201. 169. As shown in scheme 6, the Alloc group is selectively removable in the presence of the Dde group. The reverse is also true, provided that the hydrazinolysis of the Dde group is carried out in the presence of an ethylenic compound such as allyl alcohol. Otherwise, partial reduction of the allyloxycarbonyl group to propargyloxycarbonyl group is observed (Dumy, P., personal communication).
202. 170. Shapiro, G.; Buechler, D.; Ojea, V.; Pombo-Villar, E., Reuz, M.; Weber, H.-P. Tetrahedron Lett. 1993, 34, 6255-6258.
203. 171. Shapiro, G.; Buechler, D.; Enz, A.; Pombo-Villar, E. Tetrahedron Lett. 1994, 35, 1173-1176.
204. 172. Trzeciak, A.; Bannwarth, W. Tetrahedron Lett. 1992, 33, 4557-4560.
205. 173. Zhang, W.; Taylor, J. W. Tetrahedron Lett. 1996, 37, 2173-2176.
206. 174. Bastiaans, H. M. M.; van der Baan, J. L.; Ottenheijm, H. C. J. Tetrahedron Lett. 1995, 36, 5963-5966; Bastiaens, H. M.; van der Baan, J. L.; Ottenheijm, H. C. J. J. Org. Chem. 1997, 61, 3880-3889.
207. 174. Bastiaans, H. M. M.; van der Baan, J. L.; Ottenheijm, H. C. J. Tetrahedron Lett. 1995, 36, 5963-5966; Bastiaens, H. M.; van der Baan, J. L.; Ottenheijm, H. C. J. J. Org. Chem. 1997, 61, 3880-3889.
208. 175. Reviews : (a) Garg, H. G.; von dem Bruch, K.; Kunz, H. Adv. Carbohydr. Chem. Biochem. 1994, 50, 277-310;
209. (b) ref. 2a.
210. 176. Waldmann, H.; Kunz, H. Liebigs Ann. Chem. 1983, 1712-1725.
211. 177. von dem Bruch, K.; Kunz, H. Angew. Chem. Int. Ed. Engl. 1994, 33, 101-103.
212. 178. Günther, W.; Kunz, H. Angew. Chem. Int. Ed. Engl. 1990, 29, 1050-1051.
213. 179. Gill, I.; Lopez-Fandino, R.; Vulfson, E. J. Am. Chem. Soc. 1995, 117, 6175-6181.
214. 180. Lloyd-Williams, P.; Albericio, F.; Giralt, E. Tetrahedron 1993, 49, 11065-11133.
215. 181. Benz, H. Synthesis 1994, 337-358.
216. 182. McOmie, J. F. W. Chem. and Ind. 1979, 603-609.
217. 189. Kunz, H.; Dombo, B. Angew. Chem. Int. Ed. Engl. 1988, 27, 711-712.
218. 184. Kosch, W.; März, J.; Kunz, H. React. Polym. 1994, 22, 181-194.
219. 185. Seitz, O.; Kunz, H. Angew. Chem. Int. Ed. Engl. 1995, 34, 803-805.
220. 186. Frank, R.; Döring, R. Tetrahedron 1988, 44, 6031-6040.
221. 187. Guibé, F.; Dangles, O.; Balavoine, G.; Loffet, A. Tetrahedron Lett. 1989, 30, 2641-2644.
222. 188. Lloyd-Williams, P.; Jou, G.; Albericio, F.; Giralt, E. Tetrahedron Lett. 1991, 32, 4207-4210.
223. 189. Kaljuste, K.; Undén, A. Tetrahedron Lett. 1996, 37, 3031-3034.
224. 190. Giralt, E.; Eritja, R.; Pedroso, E. Tetrahedron Lett. 1981, 22, 3379-3382.
225. 191. Graul, S.T.; Schnute, M. E.; Squires, R. R. Int. J. Mass Spectrom. Ion Processes, 1990, 96(2), 181-198; Chemical Abstracts 1990, 113: 77582a.
226. 191. Graul, S.T.; Schnute, M. E.; Squires, R. R. Int. J. Mass Spectrom. Ion Processes, 1990, 96(2), 181-198; Chemical Abstracts 1990, 113: 77582a.
227. 192. Quibell, M.; Packman, L. C.; Johnson, T. J. Am. Chem. Soc. 1995, 117, 11656-11668.
228. 193. (a) Loffet, A.; Zhang, H. X. Solid Phase Synthesis Symposium Canterbury 1992 Epton R. Ed. Intercept Ltd, Andover (UK) 1992, pp77-79;
229. (b) Loffet, A.; Zhang, H. X. Int. J. Peptide Protein Res. 1993, 42, 346-351.
230. 194. Trzeciak, A.; Vorberr, Th.; Bannwarth, W. Proceedings of the 22nd European Peptide Symposium, Schneiber C. H. and Eberle, A. N. Eds.; ESCOM, Leiden, 1993, pp 342-344.
231. 195. Crivici, A.; Lajoie, G. Synth. Commun. 1993, 23, 49-53.
232. 196. Belshaw, P. J.; Mzengeza, S.; Lajoie, G. A. Synth. Commun. 1990, 20, 3157-3160.
233. 197. Loffet, A.; Zhang, H. X.; Swain, P. A., Krotzer, N.; J. Fuller, W. D., Goodman, M. Proceedings of the 1992 Chinese Peptide Symposium, 1992, Hangzhou (China); Du, Y.-C.; Tam, J. P.; Zhang, Y-S. Eds, ESCOM, Leiden, pp. 291-294.
234. 198. The N-indolyl-Alloc derivative of tryptophane has not been tested in this reaction.
235. 199. Malanda-Kimbonguila, A.; Merzouk, A.; Guibé, F.; Loffet, A. Tetrahedron Lett. 1994, 55, 9035-9038.
236. 104 On the other hand, palladium catalysed allylation of ethylthiotrimethylsilane by allylic carbonates and epoxides has been reported (Trost, B. M.; Scanlan, T. S. Tetrahedron Lett. 1986, 27, 4141-4144).
237. 201. acyl-iminium species: Speckamp, W. N.; Hiemstra, H. Tetrahedron 1985, 41, 4367-4416 and refs therein.
238. 202. Jones, J. The Chemical Synthesis of Peptides, Oxford University Press, 1991.
239. 203. Fletcher, A. R.; Jones, J. H.; Ramage, W. I.; Staculski, A. V. J. Chem. Soc. Perkin Trans. I. 1979, 2261-2266.
240. 204. Malanda-Kimbonguila, A.; Boucida, S.; Guibé, F.; Loffet, A. Tetrahedron 1997, 53, 12525-12538.
241. 205. Hayakawa, Y.; Nobori, T.; Noyori, R.; Imai, J. Tetrahedron Lett. 1987, 28, 2623-2626.
242. 206. Sekine, M. J. Org. Chem. 1989, 54, 2321-2326.
243. 207. Hayakawa, Y.; Hirose, M.; Hayakawa, M.; Noyori, R. J. Org. Chem. 1995, 60, 925-930.
244. 208. Zhang, X.; Jones, R. A. Tetrahedron Lett. 1996, 37, 3789-3790.
245. 209. Kunz, H.; Birnbach, S. Tetrahedron Lett. 1984, 25, 3567-3570.
246. 210. Minami, I.; Yukara, M.; Tsuji, J. Tetrahedron Lett. 1987, 28, 2737-2740
247. 211. Mastalerz, H. J. Org. Chem. 1984, 49, 4092-4094.
248. 212. For recent examples of use of the Alloc group for hydroxyl group protection in carbohydrates, see refs 18 and 145.
249. 213. Brill, W. K. D.; Kunz, H. Synlett 1991, 193-194.
250. 214. Ho T.-L. Synth. Commun. 1978, 8, 15-17.
251. 215. Corey, E. J.; Tius, M. A. Tetrahedron Lett. 1978, 2081-2082
252. 216. Corey, E. J.; Suggs, J. W. J. Org. Chem. 1973, 38, 3223-3224.
253. 217. Schmid, C. R. Tetrahedron Lett. 1992, 33, 757-760.
254. 218. Evans, D. A.; Dinsmore, C. J.; Ratz, A. M.; Evrard, D. A.; Barrow, J. C. J. Am. Chem. Soc. 1997, 119, 3417-3418.
255. 219. Myers, A. G.; Tom, J. T.; Fraley, M. E.; Cohen, S. B.; Madar, D. J. J. Am. Chem. Soc. 1997, 119, 6072-6094.
256. 220. Flouzat, C.; Marguerite, F.; Croizet, F.; Percebois, M.; Monteil, A.; Combourieu, M. Tetrahedron Lett. 1997, 38, 1191-1194.
257. 221. Lee, J., Griffin, J. H., Nicas, T. I. J. Org. Chem. 1996, 61, 3983-3986.
258. 222. Emery, F.; Bisang, C.; Favre, M.; Jian, L.; Robinson, J. A. J. Chem. Soc. Chem. Commun. 1996, 2155-2156.
259. 223. Davies, M.; Bradley, M. Ang. Chem. Int. Ed. Engl. 1997, 36, 1097-1099.
260. 224. Kania, R. S.; Zuckerman, R. N.; Marlowe, C. K. J. Am. Chem. Soc. 1994, 116, 8835-8836.
261. 225. Andrews, M. J. I.; Tabor, A. B. Tetrahedron Lett. 1997, 38, 3063-3066.
262. 226. Probert, J. M.; Rennex, D.; Bradley, M. Tetrahedron Lett. 1996, 37, 1101-1104.
263. 227. Lemaire-Audoire, S.; Savignac, M.; Blart, E.; Bernard, J.-M.; Genêt, J.-P Tetrahedron Lett. 1997, 38, 2955-2958.
264. 228. Thieriet, N.; Alsina, J.; Giralt, E.; Guibé, F.; Albericio, F. Tetrahedron Lett. 1997, 38, 7275-7278.
265. 229. Seitz, O.; Kunz, H. J. Org. Chem. 1997, 62, 813-826.
266. 230. Habermann, J.; Seitz, O.; Kunz, H. "Allylic anchoring groups and pentafluorophenyluronium reagents in the solid phase synthesis of glycopeptides." Communication at the fifth internal symposium on Solid Phase Synthesis and Combinatorial Chemical Libraries, London (UK.), 2nd-6th September, 1997.
267. 231. Orsat, B.; Alper, P. B.; Moree, W.; Mak, C.-P., Wong, C.-H. J. Am. Chem. Soc. 1996, 118, 712-713.