Developments in the deprotection of thioacetals

Journal of Sulfur Chemistry

Volumn 26, Issue 4-5, 2005, Pages 411-427

  Burghardt, T E ^a  

^a Johns Manville   (United States)

Author keywords

Deprotection; Dithiane; Dithiolane; Hydrolysis; Thioacetal

Indexed keywords

CARBONYL COMPOUNDS;

ACIDIC CONDITIONS; BASIC CONDITIONS; DEPROTECTION; DITHIANES; DITHIOACETALS; DITHIOLANES; FORMATION STABILITY; PROTECTING GROUP; THIOACETALS; UMPOLUNG;

HYDROLYSIS;

EID: 31144443044     PISSN: 17415993     EISSN: 17416000     Source Type: Journal    
DOI: 10.1080/17415990500195198     Document Type: Review

References (148)

1. B.-T. Gröbel, D. Seebach. Synthesis, 357 (1977).
2. P.C.B. Page, M.B. van Niel, J.C. Prodger. Tetrahedron, 45, 7643 (1989).
3. M. Schelhaas, H. Waldmann. Angew. Chem., 108, 2192 (1996);
4. Angew. Chem., Int. Ed., 35, 2056 (1996).
5. A.K. Banerjee, M.S. Laya. Russ. Chem. Rev., 69, 947 (2000).
6. M. Yus, C. Nájera, F. Foubelo. Tetrahedron, 59, 6147 (2003).
7. A.R. Hajipour, S. Khoee, A.E. Ruoho. Org. Prep. Proc. Int., 35, 527 (2003).
8. A.B. Smith, C.M. Adams. Acc. Chem. Res., 37, 365 (2004).
9. P.J. Kocieński. Protecting groups, 3rd ed., pp. 77-92, Georg Thieme, Stuttgart (2004).
10. S. Deflora, C. Bennicelli, M. Bagnasco. Mutat. Res., 317, 57 (1994).
11. K. Schumann, B. Elsenhans. J. Trace Elem. Med. Biol., 16, 139 (2002).
12. C.G. Daughton. Environ. Health Persp., 111, 775 (2003).
13. T.H. Fife, E. Anderson. J. Am. Chem. Soc., 92, 5464 (1970).
14. C. Moreau, J. Lecomte, S. Mseddi, N. Zmimita. J. Mol. Cat. A, 125, 143 (1997).
15. D.P.N. Satchell, R.S. Satchell. Chem. Soc. Rev., 55 (1990).
16. M. Ali, D.P.N. Satchell. J. Chem. Soc., Chem. Commun., 866 (1991).
17. E. Fisher. Ber. Dtsch. Chem. Ges., 27, 673 (1894).
18. $13 for deprotection of 100 mmol of dithiane [2005 Aldrich U.S. prices].
19. S. Hanessian, J. Ma, W. Wang. J. Am. Chem. Soc., 123, 10200 (2001).
20. E. Vedejs, P.L. Fuchs. J. Org. Chem., 36, 366 (1971).
21. I. Degani, R. Fochi, V. Regondi. Synthesis, 51 (1981).
22. E. Fujita, Y. Nagao, K. Kaneko. Chem. Pharm. Bull., 26, 3743 (1978).
23. $90 for deprotection of 100 mmol of dithiane [2005 Aldrich U.S. prices]
24. A.B. Smith, W. Zhu, S. Shirakami, C. Sfoggatakis, V.A. Doughty, C.S. Bennett, Y. Sakamoto. Org. Lett., 5, 761 (2003).
25. A. Armstrong, P.A. Barsanti, L.H. Jones, G. Ahmed. J. Org. Chem., 65, 7020 (2000).
26. A.B. Smith, A.T. Lupo, M. Ohba, K. Chen. J. Am. Chem. Soc., 111, 6648 (1989).
27. V. Janout, S.L. Regen. J. Org. Chem., 47, 2212 (1982).
28. E.J. Corey, B.W. Erickson. J. Org. Chem., 36, 3553 (1971).
29. H. Kotosuki, T. Kosumi, M. Inoue, Y. Ushio, M. Ochi. Tetrahedron Lett., 32, 4159 (1991).
30. M.H. Habibi, S. Tangestaninejad, M. Montazerozohori, I. Mohamadpoor-Baltork. Molecules, 8, 663 (2003).
31. 2O [2005 Aldrich U.S. prices].
32. C.A. Reece, J.O. Rodin, R.G. Brownlee, W.G. Duncan, R.M. Silverstein. Tetrahedron, 24, 4249 (1968).
33. D. Gravel, C. Vaziri, S. Rahal. J. Chem. Soc., Chem. Commun., 1323 (1972).
34. A.J. Sutherland, J.K. Sutherland, P.J. Crowley. J. Chem. Soc., Perkin Trans. 1, 349 (1996).
35. D. Penn, Z. Saidi, D.P.N. Satchell, R.S. Satchell. J. Chem. Res. (S), 200 (1987).
36. K. Nishide, K. Yokota, D. Nakamura, T. Sumiya, M. Node, M. Ueda, K. Fuji. Tetrahedron Lett., 34, 3425 (1993).
37. Y. Nagao, K. Kaneko, M. Ochiai, E. Fujita. J. Chem. Soc., Chem. Commun., 202 (1976).
38. E. Fujita, Y. Nagao, K. Kaneko. Chem. Pharm. Bull., 24, 1115 (1976).
39. Y. Nagao, K. Seno, E. Fujita. Tetrahedron Lett., 20, 3167 (1979).
40. T. Harayama, H. Cho, Y. Inubushi. Tetrahedron Lett., 18, 3167 (1977).
41. T.-S. Ho, H.-C. Ho, C.M. Wong. J. Chem. Soc., Chem. Commun., 791 (1972).
42. H.-J. Cristeau, B. Chabaud, R. Labaudinière, H. Christol. Synth. Commun., 11, 423 (1981).
43. W.-T. Jiaang, H.-C. Lin, K.-H. Tang, L.-B. Chang, Y.-M. Tsai. J. Org. Chem., 64, 618 (1999).
44. T. Mukaiyama, K. Narasaka, M. Furusato. J. Am. Chem. Soc., 94, 8642 (1972).
45. K. Suenaga, K. Araki, T. Sengoku, D. Uemura. Org. Lett., 3, 527 (2001).
46. K. Araki, K. Suenaga, T. Sengoku, D. Uemura. Tetrahedron, 58, 1983 (2002).
47. A. Vakalopoulos, H.M.R. Hoffmann. Org. Lett., 3, 2185 (2001).
48. K. Saigo, Y. Hashimoto, N. Kihara, H. Umehara, M. Hasegawa. Chem. Lett., 831 (1990).
49. A. Kamal, E. Laxman, P.S.M.M. Reddy. Synlett, 1476 (2000).
50. S.J. Daum, R.L. Clarke. Tetrahedron Lett., 8, 165 (1967).
51. P.R. Heaton, J.M. Midgley, W.B. Whalley. J. Chem. Soc., Chem. Commun., 750 (1971).
52. F. Weygand, H.J. Bestmann, H. Ziemann. Chem. Ber., 91, 1040 (1958).
53. H. Zinner, H. Brandhoff, H. Schmandke, H. Kristen, R. Haun. Chem. Ber., 92, 3151 (1959).
54. G.S. Bates, J. O'Doherty. J. Org. Chem., 46, 1745 (1981).
55. M.T.M. El-Wassimy, K.A. Jørgensen, S.O. Lawesson. J. Chem. Soc., Perkin Trans. 1, 2201 (1983).
56. G.A. Olah, S.C. Narang, G.F. Salem. Synthesis, 657 (1980).
57. 3 needed to deprotect 100 mmol of dithiane [2005 Aldrich U.S. prices].
58. D.R. Williams, P.A. Jass, H.-L.A. Tse, R.D. Gaston. J. Am. Chem. Soc., 112, 4552 (1990).
59. P.V. Ramachandran, M.T. Rudd, T.E. Burghardt, M.V.R. Reddy. J. Org. Chem., 68, 9310 (2003).
60. G.A. Russel, L.A. Ochrymowicz. J. Org. Chem., 34, 3618 (1969).
61. S.P. Chavan, P.B. Soni, R.R. Kale, K. Pasupathy. Synth. Commun., 33, 879 (2003).
62. G. Stork, K. Zhao. Tetrahedron Lett., 30, 287 (1989).
63. $178 for deprotection of 100 mmol of dithiane [2005 Aldrich U.S. prices].
64. X.-X. Shi, Q.-Q. Wu. Synth. Commun., 30, 4081 (2000).
65. V.A. Keller, J.R. Martinelli, S.R. Strieter, S.D. Burke. Org. Lett., 4, 467 (2002).
66. K.C. Nicolaou, Y. Li, K. Sugita, H. Monenschein, P. Guntupalli, H.J. Mitchell, K.C. Fylaktakidou, D. Vourloumis, P. Giannakakou, A. O'Brate. J. Am. Chem. Soc., 125, 15443 (2003).
67. F.F. Fleming, L. Funk, R. Altundas, Y. Tu. J. Org. Chem., 66, 6502 (2001).
68. D.B. Dess, J.C. Martin. J. Org. Chem., 48, 4155 (1983).
69. N.F. Langille, L.A. Dakin, J.S. Panek. Org. Lett., 5, 575 (2003).
70. E.J. Corey, M.-C. Kang, M.C. Desai, A.K. Ghosh, I.N. Houpis. J. Am. Chem. Soc., 110, 649 (1988).
71. X.-X. Shi, S.P. Khanapure, J. Rokach. Tetrahedron Lett., 37, 4331 (1996).
72. K.C. Nicolaou, C.J.N. Mathison, T. Montagnon. Angew. Chem., Int. Ed., 42, 4077 (2003).
73. K.C. Nicolaou, C.J.N. Mathison, T. Montagnon. J. Am. Chem. Soc., 126, 5192 (2004).
74. Y. Wu, X. Shen, J.-H. Huang, C.-J. Tang, H.-H. Liu, Q. Hu. Tetrahedron Lett., 43, 6443 (2002).
75. N.S. Krishnaveni, K. Surendra, Y.V.D. Ageswar, K.R. Rao. Synthesis, 2295 (2003).
76. R.A. Hajipour, A.E. Ruoho. Sulfur Lett., 26, 181 (2003).
77. J. Cossy. Synthesis, 1113 (1987).
78. A.B. Smith, B.D. Dorsey, M. Visnick, T. Maeda, M.S. Malamas. J. Am. Chem. Soc., 108, 3110 (1986).
79. P. Ceccherelli, M. Curini, M.C. Marcotullio, F. Epifano, O. Rosati. Synlett, 767 (1996).
80. A.R. Hajipour, S.A. Pourmousavi, A.E. Ruoho. J. Sulfur Chem., 25, 401 (2004).
81. H. Ikehira, S. Tanimoto, T. Oida, M. Okano. Synthesis (Stuttgart), 1087 (1982).
82. H.-J. Liu, V. Wiszniewski. Tetrahedron Lett., 29, 5471 (1988).
83. J. Liu, C.-H. Wong. Tetrahedron Lett., 43, 4037 (2002).
84. L. Matthew, S. Sankararaman. J. Org. Chem., 58, 7576 (1993).
85. K. Tanemura, H. Doha, M. Imamura, T. Suzuki, T. Horaguchi. Chem. Lett., 965 (1994).
86. K. Tanemura, H. Doha, M. Imamura, T. Suzuki, T. Horaguchi. J. Chem. Soc., Perkin Trans. 1, 453 (1996).
87. H. Firouzabadi, N. Iranpoor, H. Hazarkhani. Phosphorus, Sulfur, Silicon, 177, 2571 (2002).
88. R.A. Hajipour, S.E. Mallakpour, I. Mohammadpoor-Baltork, H. Adibi. Molecules, 7, 674 (2002).
89. H. Firouzabadi, H. Hazarkhani, B. Karimi, U. Niroumand, S. Ghassamipour. Proc. Electr. Conf. Synth. Org. Chem. (ECSOC-4, www.mdpi.org), A0044 (2000).
90. S.A. Haroutounian. Synthesis, 39 (1995).
91. W.F.J. Huurdeman, H. Wynberg, D.W. Emerson. Tetrahedron Lett., 12, 3445 (1971).
92. D.W. Emerson, H. Wynberg. Tetraherdon Lett., 12, 3449 (1971).
93. M. Curini, M.C. Marcotullio, E. Pisani, O. Rosati, U. Costantino. Synlett, 769 (1997).
94. M. Prato, U. Quintily, G. Scorrano, A. Sturaro. Synthesis, 679 (1982).
95. H. Firouzabadi, N. Iranpoor, H. Hassani, S. Sobhani. Synth. Commun., 34, 1967 (2004).
96. A.R. Hajipour, A.E. Ruoho. Sulfur Lett., 25, 151 (2002).
97. D. Ghiringhelli. Synthesis, 580 (1982).
98. A.K. Shukla, M. Verma, K.N. Singh. Indian J. Chem., Sect. B. 43, 1748 (2004).
99. G.A. Olah, S.C. Narang, A. Garcia-Luna, G.F. Salem. Synthesis, 146 (1981).
100. D. Crich, J. Picione. Synlett, 1257 (2003).
101. T. Ichige, A. Miyake, N. Kanoh, M. Nakata. Synlett, 1686 (2004).
102. M. Ohshima, M. Mukarami, T. Mukaiyama. Chem. Lett., 1593 (1996).
103. T. Ravindranathan, S.P. Chavan, R.B. Tejwani, J.P. Varghese. J. Chem. Soc., Chem. Commun., 1750 (1991).
104. T. Ravindranathan, S.P. Chavan, M.M. Awachat. Tetrahedron Lett., 35, 8835 (1994).
105. G. Solladié, V. Berl. Bull. Soc. Chim. Fr., 130, 568 (1993).
106. C.S. Rao, M. Chandrasekharma, H. Ila, H. Junjappa. Tetrahedron Lett., 33, 8163 (1992).
107. J.B. Chattopadhyaya, A.V.R. Rao. Tetrahedron Lett., 14, 3735 (1973).
108. G.A. Olah, A.K. Mahrotra, S.C. Narang. Synthesis, 151 (1982).
109. G.A. Olah, S.C. Narang, A.K. Mahrotra. Synthesis, 965 (1982).
110. H. Firouzabadi, N. Iranpoor, H. Hazarkhani, B. Karimi. J. Org. Chem., 67, 2572 (2002).
111. B. Karimi, H. Hazarkhani. Synthesis, 2547 (2003).
112. N. Iranpoor, H. Firouzabadi, H.R. Shaterian. Tetrahedron Lett., 44, 4769 (2003).
113. H. Firouzabadi, B. Karimi. Phosphorus, Sulfur, Silicon, 175, 207 (2001).
114. M. Fetizon, M. Jurion. J. Chem. Soc., Chem. Commun., 382 (1972).
115. H.-L.W. Chang. Tetrahedron Lett., 13, 1989 (1972).
116. $8 for hydrolysis of 100 mmol of dithiane [2005 Aldrich U.S. prices].
117. A.G. Myers, C.R. Condroski. J. Am. Chem. Soc., 115, 7926 (1993).
118. T. Oishi, H. Takechi, K. Kamemoto, Y. Ban. Tetrahedron Lett., 15, 11 (1974).
119. I. Stahl. Synthesis, 135 (1981).
120. K. Fuji, K. Ichikawa, E. Fujita. Tetrahedron Lett., 19, 3561 (1978).
121. A.T. Khan, E. Mondal, P.R. Sahu. Synlett, 377 (2003).
122. M. Balogh, A. Cornélis, P. Laszlo. Tetrahedron Lett., 25, 3313 (1984).
123. A. Cornélis, P. Laszlo. Synthesis, 909 (1985).
124. P. Laszlo, A. Cornélis. Aldrichimica Acta, 21, 97 (1988).
125. J.G. Lee, J.P. Hwang. Chem. Lett., 507 (1995).
126. M. Hirano, K. Ukawa, S. Yakabe, T. Morimoto. Synth. Commun., 27, 1527 (1997).
127. P. Wipf, M.J. Soth. Org. Lett., 4, 1787 (2002).
128. H.M. Meshram, G.S. Reddy, G. Sumitra, J.S. Yadav. Synth. Commun., 29, 1113 (1999).
129. B.P. Bandgar, S.P. Kasture. Green Chem., 2, 156 (2000).
130. N. Komatsu, A. Taniguchi, M. Uda, H. Suzuki. Chem. Commun., 1847 (1996).
131. N. Komatsu, A. Taniguchi, S. Wada, H. Suzuki. Adv. Synth. Catal., 343, 473 (2001).
132. $4 for deprotection of 100 mmol of dithiane [2005 Aldrich U.S. prices].
133. G. Mehta, R. Uma. Tetrahedron Lett., 37, 1897 (1996).
134. H. Firouzabadi, N. Iranpoor, M.A. Zolfigo. Bull. Chem. Soc. Jpn., 71, 2169 (1998).
135. M. Kamata, S. Otogawa, E. Hesegawa. Tetrahedron Lett., 32, 7421 (1991).
136. M. Schmittel, M. Levis. Synlett, 315 (1996).
137. G.A. Epling, Q. Wang. Tetrahedron Lett., 33, 5909 (1992).
138. M. Kamata, Y. Kato, E. Hasegawa. Tetrahedron Lett., 32, 4349 (1991).
139. E. Fasani, M. Freccero, M. Mella, A. Albini. Tetrahedron, 53, 2219 (1997).
140. M. Kamata, Y. Murakami, Y. Tamagawa, M. Kato, E. Hasegawa. Tetrahedron, 50, 12821 (1994).
141. M. Kamata, M. Sato, E. Hasegawa. Tetrahedron Lett., 33, 5085 (1992).
142. M. Platen, E. Steckhan. Chem. Ber., 117, 1679 (1984).
143. M.H. Habibi, S. Tangestaninejad, I. Mohammadpoor-Baltork, M. Montazeroezohori. Phosphorus, Sulfur, Silicon, 179, 597 (2004).
144. Q.N. Porter, J.H.P. Utley. J. Chem. Soc., Chem. Commun., 255 (1978).
145. A. Lebous, J. Simonet, J. Gelas, A. Dehbi. Synthesis, 320 (1987).
146. M. Kimura, H. Kawai, Y. Sawaki. Electrochemica Acta, 42, 497 (1997).
147. L.A. Barnhurst, Y. Wan, A.G. Kutateladze. Org. Lett., 2, 799 (2000).
148. I.T. Horváth. Chem. Rev., 95, 1 (1995).