A novel multistep mechanism for the stereocontrolled ring opening of hindered sulfamidates: Mild, green, and efficient reactivity with alcohols

Chemistry - A European Journal

Volumn 15, Issue 38, 2009, Pages 9810-9823

  Jiménez Osés, Gnzalo ^a   Avenoza, Alberto ^a   Busto, Jesús H ^a   Rodríguez, Fernando ^a   Peregrina, Jesús M ^a  

^a UNIVERSITY OF LA RIOJA   (Spain)

Author keywords

Alcohols; Neighboringgroup effects; Nucleophilic substitution; Reaction mechanisms; Sulfamidates

Indexed keywords

BASIC CONDITIONS; CHEMOSELECTIVE; INVERSION OF CONFIGURATION; MULTI-STEP MECHANISM; NEIGHBORING-GROUP EFFECTS; NUCLEOPHILIC SUBSTITUTION; NUCLEOPHILIC SUBSTITUTION REACTIONS; OXAZOLINIUM; QUATERNARY CENTERS; REACTION CONDITIONS; RING OPENING; RING OPENING REACTION; SYNTHETIC ROUTES;

AROMATIC HYDROCARBONS; FLUORINE CONTAINING POLYMERS; FUNCTIONAL GROUPS; SOLVENTS;

CHEMICAL ACTIVATION;

EID: 70450184675     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.200900710     Document Type: Article

References (135)

1. (a) B. B. Lohray, Synthesis 1992, 1035-1052;
2. (b) D. M. Hodgson, A. R. Gibbs, G. P. Lee, Tetrahedron 1996, 52, 14361-14384;
3. (c) C. Lauret, Tetrahedron: Asymmetry 2001, 12, 2359-2383;
4. (d) I. M. Pastor, M. Yus, Curr. Org. Chem. 2005, 9, 1-29;
5. e) D. Amantini, F. Fringuelli, O. Piermatti, S. Tortoioli, L. Vaccaro, Arkivoc 2002, 11, 293-311;
6. f) X. E. Hu, Tetrahedron 2004, 60, 2701-2743;
7. g) Aziridines and Epoxides in Organic Synthesis (Ed.: A. K. Yudin), WileyVCH, Weinheim, 2006;
8. h) J. G. Smith, Synthesis 1984, 629-656.
9. a) M. K. Ghoray, K. Das, D. Shukla, J. Org. Chem. 2007, 72, 5859-5862;
10. b) J. S. Yadav, B. V. S. Reddy, E. Balanarsaiah, S. Raghavendra, Tetrahedron Lett. 2002, 43, 5105-5107;
11. (c) E. M. Forbeck, C. D. Evans, J. A. Gilleran, P. Li, A. M. Joullié, J. Am. Chem. Soc. 2007, 129, 14463-14469;
12. (d) B. A. B. Prasad, R. Sanghi, V. K. Singh, Tetrahedron 2002, 58, 7355-7363;
13. e) P. Maligres, M. M. See, D. Askin, P. J. Reider, Tetrahedron Lett. 1997, 38, 5253-5256;
14. f) C. Schneider, Synthesis 2006, 3919-3944.
15. a) R. E. Meléndez, W. D. Lubell, Tetrahedron 2003, 59, 2581-2616 and references cited therein;
16. b) K. C. Nicolaou, S. A. Snyder, D. A. Longbottom, A. Z. Nalbandian, X. Huang, Chem. Eur. J. 2004, 10, 5581 -5606;
17. (c) K. C. Nicolaou, X. Huang, S. A. Snyder, P. B. Rao, M. Bella, M. V. Reddy, Angew. Chem. 2002, 114, 862-866;
18. Angew. Chem. Int. Ed. 2002, 41, 834-837;
19. (d) J. F Bower, J. Svenda, A. J. Williams, J. P. H. Charmant, R. M. Lawrence, P. Szeto, T. Gallagher, Org. Lett. 2004, 6, 4727-4730;
20. e) A. J. Williams, S. Chakthong, D. Gray, R. M. Lawrence, T. Gallagher, Org. Lett. 2003, 5, 811-814;
21. f) J. J. Posakony, T. J. Tewson, Synthesis 2002, 859-864;
22. g) H.-S. Byun, L. He, R. Bittman, Tetrahedron 2000, 56, 7051-7091;3
23. h) A. Avenoza, J. H. Busto, F. Corzana, J. I. Garcia, J. M. Peregrina, J. Org. Chem. 2003, 68, 4506-4513;
24. (i) F. Galaud, J. W. Blankenship, W. D. Lubell, Heterocycles 2008, 76, 1121-1131;
25. (j) F. Galaud, W. D. Lubell, Biopolymers 2005, 80, 665-674;
26. (k) M. Atfani, L. Wei, W. D. Lubell, Org. Lett. 2001, 3, 2965-2968;
27. A. G. Jamieson, N. Boutard, K. Beauregard, M. S. Bodas, H. Ong, C. Quiniou, S. Chemtob, W. D. Lubell, J. Am. Chem. Soc. 2009, 131, 7917-7927.
28. See, for example: a) D. F. Shellhamer, D. T. Anstine, K. M. Gallego, B. R. Ganesh, A. A. Hanson, K. A. Hanson, R. D. Henderson, J. M. Prince, V. L. Heasley, J. Chem. Soc. Perkin Trans. 2 1995, 861-866;
29. b) A. Nishinaga, S. Wakabayashi, Chem. Lett. 1978, 913-914;
30. (c) C. S. Poorker, J. Kagan, Tetrahedron Lett. 1985, 26, 6405-6408;
31. (d) F. Latif, M. S. Shekhani, W. J. Voelter, J. Chem. Soc. Perkin Trans. 1 1990, 1573-1575;
32. e) S. Y. Ko, M. Malik, A. F. Dickinson, J. Org. Chem. 1994, 59, 2570-2576;
33. f) A. Baran, A. Günel, M. Balci, J. Org. Chem. 2008, 73, 4370-4375;
34. g) A. A. Bredikhin, A. V. Pashagin, Z. A. Brekikhina, S. N. Lazarev, A. T. Gubaidullin, I. A. Litvinov, Russ. Chem. Bull. 2000, 109, 1575-1582;
35. h) E. Kuyl-Yeheskiely, M. Lodder, G. A. van der Marel, J. H. van Boom, Tetrahedron Lett. 1992, 33, 3013-3016;
36. (i) B. Olofsson, R. Wijtmans, P. Somfai, Tetrahedron 2002, 58, 5979-5982;
37. j) N. A. Khanjin, M. Hesse, HeIv. Chim. Acta 2003, 86, 2028-2057;
38. k) M. Pilkington, J. D. Wallis, J. Chem. Soc. Chem. Commun. 1993, 1857-1858.
39. a) M. W. C. Robinson, R. Buckle, I. Mabbett, G. M. Grant, A. E. Graham, Tetrahedron Lett. 2007, 48, 4723-4725;
40. b) B. A. B. Prasad, R. Sanghi, V. K. Singh, Tetrahedron 2002, 58, 7355-7363;
41. (c)J. S. Yadav, B. V. S. Reddy, E. Balanarsaiah, S. Raghavendra, Tetrahedron Lett. 2002, 43, 5105-5107;
42. (d) P. R. Likhar, M. P. Kumar, A. K. Bandyopadhyay, Synlett 2001, 836-838;
43. e) H. Fironzabadi, N. Iranpoor, A. A. Jafari, S. Makarem, J. Mol. Catal. A 2006, 250, 237-242;
44. f) W. J. Sanders, L. L. Kiessling, Tetrahedron Lett. 1994, 35, 7335-7338;
45. g) D. D. Manning, C. R. Bertozzi, N. L. Pohl, S. D. Rosen, L. L. Kiessling, J. Org. Chem. 1995, 60, 6254-6255;
46. h) F. E. McDonald, P. Vadapally, Tetrahedron Lett. 1999, 40, 2235-2238;
47. (i)K. Nakajima, M. Neya, S. Yamada, K. Okawa, Bull. Chem. Soc. Jpn. 1982, 55, 3049-3050.
48. a) Z. Wang, Y.-T. Cui, Z.-B. Xu, J. Qu, J. Org. Chem. 2008, 73, 2270-2274;
49. b) S. Bonollo, F Fringelli, F. Pizzo, L. Vaccaro, Green Chem. 2006, 8, 960-964;
50. (c) N. Azizi, M. R. Saidi, Org. Lett. 2005, 7, 3649-3651.
51. a) H. Shao, Q. Zhu, M. Goodman, J. Org. Chem. 1995, 60, 790-791;
52. b) C. Palomo, J. M. Aizpurua, E. Balentova, A. Jimenez, J. Oyarbide, R. M. Fratila, J. I. Miranda, Org. Lett. 2007, 9, 101-104;
53. (c) B. G. M. Burgaud, D. C. Horwell, A. Padova, M. C. Pritchard, Tetrahedron 1996, 52, 13035-13050;
54. (d) B. L. Kedrowski, C. H. Heathcock, Heterocycles 2000, 58, 601-634;
55. e) U. K. Nadir, A. Singh, Tetrahedron Lett. 2005, 46, 2083-2086;
56. f) P. Dauban, R. H. Dodd, Tetrahedron Lett. 1998, 39, 5739-5742;
57. g) Å. Sjöholm-Timen, A. Fischer, P. Somfai, Chem. Commun. 2003, 1150-1151;
58. h) Å. Sjöholm-Timen, P. Somfai, J. Org. Chem. 2003, 68, 9958-9963;
59. (i) U. K. Nadir, R. V. Krishna, A. Singh, Tetrahedron Lett. 2005, 46, 479-482;
60. j) M. E. Tanner, S. Miao, Tetrahedron Lett. 1994, 35, 4073-4076.
61. P. H. Di Chenna, F Robert-Peillard, P. Dauban, R. H. Dodd, Org. Lett. 2004, 6, 4503-4505.
62. a) S. F Martin, Tetrahedron 1980, 36, 419-460;
63. b) K. Fuji, Chem. Rev. 1993, 93, 2037-2066;
64. (c)E. J. Corey, A. Guzmán-Pérez, Angew. Chem. 1998, 110, 2092-2118;
65. Angew. Chem. Int. Ed. 1998, 37, 388-401;
66. (d) I. Denissova, L. Barriault, Tetrahedron 2003, 59, 10105-10146;
67. e) M. Kimura, T. Yamazaki, T. Kitazume, T. Kubota, Org. Lett. 2004, 6, 4651-4654;
68. f) Quaternary Stereocenters: Challenges and Solutions for Organic Synthesis (Eds.: A. Baro, J. Christoffers), Wiley-VCH, Weinheim, 2005.
69. a) R. P. Cheng, S. H. Gellman, W. F DeGrado, Chem. Rev. 2001, 101, 3219-3232;
70. b) M. Liu, M. P. Sibi, Tetrahedron 2002, 58, 7991-8035;
71. (c) D. Seebach, A. K. Beck, D. J. Bierbaum, Chem. Biodiversity 2004, 1, 1111-1239;
72. (d) D. Seebach, T. Kimmerlin, R. Sebesta, M. A. Campo, A. K. Beck, Tetrahedron 2004, 60, 7455-7506;
73. e) Enantioselective Synthesis of ß-Amino Acids, 2nd ed. (Eds.: E. Juaristi, V. Soloshonok), Wiley, New Jersey, 2005;
74. f) B. R. Huck, S. H. Gellman, J. Org. Chem. 2005, 70, 3353-3362;
75. g) F. Fülöp, T. A. Martinek, G. K. Tóth, Chem. Soc. Rev. 2006, 35, 323-334.
76. S. Abele, D. Seebach, Eur. J. Org. Chem. 2000, 1-15.
77. a) A. Guerrini, G. Varchi, C Samori, R. Daniele, B. Arturo, Tetrahedron Lett. 2007, 48, 5081-5085;
78. b) Y. Huang, Y. B. Zhang, Z. C. Chen, P. F Xu, Tetrahedron: Asymmetry 2006, 17, 3152-3157;
79. (c) A. Avenoza, J. H. Busto, F. Corzana, G. Jiménez-Osés, M. París, J. M. Peregrina, D. Sucunza, M. M. Zurbano, Tetrahedron: Asymmetry 2004, 15, 131-137;
80. (d) C. Cativiela, M. D. Díaz de Villegas, J. A. Gálvez, Tetrahedron 1996, 52, 687-694;
81. e) R. Pires, K. Burger, Synthesis 1996, 1277-1279.
82. a) D. L. Steer, R. A. Lew, P. Perlmutter, A. I. Smith, M. I. Aguilar, Curr. Med. Chem. 2002, 9, 811;
83. b) S. Jaracz, J. Chen, L. V. Kuznetsova, I. Ojima, Bioorg. Med. Chem. 2005, 13, 5043.
84. A. Avenoza, J. H. Busto, F Corzana, G. Jiménez-Osés, J. M. Peregrina, Chem. Commun. 2004, 980.
85. a) A. Avenoza, J. H. Busto, G. Jiménez-Osés, J. M. Peregrina, J. Org. Chem. 2006, 71, 1692;
86. b) A. Avenoza, J. H. Busto, G. Jiménez-Osés, J. M. Peregrina, Org. Lett. 2006, 8, 2855;
87. (c) A. Avenoza, J. H. Busto, G. Jiménez-Osés, J. M. Peregrina, Synthesis 2006, 641;
88. (d) A. Avenoza, J. H. Busto, G. Jiménez-Osés, J. M. Peregrina, J. Org. Chem. 2005, 70, 5721;
89. e) A. Avenoza, J. H. Busto, F. Corzana, G. Jiménez-Osés, J. M. Peregrina, Phosphorus Sulfur Silicon Relat. Elem. 2005, 180, 1459.
90. G. Jiménez-Osés, A. Avenoza, J. H. Busto, J. M. Peregrina, Tetrahedron: Asymmetry 2008, 19, 443.
91. D. Alker, K. J. Doyle, L. M. Harwood, A. McGregor, Tetrahedron: Asymmetry 1990, 1, 877.
92. We assayed the reaction of (R)-1b with a lower amount of methanol (1:10 in volume, 25 equiv with respect to sulfamidate) in other nonnucleophilic and nucleophilic solvents at 80°C As non-nucleophilic solvents, 2,2,2-trifluoroethanol, 1,1,1,3,3,3-hexafluoropropanol, tertbutanol, nitromethane, and toluene were used while water, N,N-dimethylformamide, and dimethylsulfoxide were used as nucleophilic solvents. Unfortunately, with the former the sulfamidate remained unreacted after 24 h of stirring and the latter led to a complex reaction mixture. Only few-butanol allowed us to obtain a discrete conversion of (S)-3b (16% after 24h), but a prolonged heating (one week) decomposed the reactants to give a rather complex mixture.
93. W. Makulski, J. Mol. Struct. 2005, 744-747, 439446.
94. Z. Syrgiannis, Y. Elemes, Tetrahedron Lett. 2006, 47, 6831-6834.
95. a) H. C Brown, G. J. McDonald, J. Am. Chem. Soc. 1966, 88, 2514-2519;
96. b) H. C. Brown, M. E. Azzaro, J. G. Koelling, G. J. McDonald, J. Am. Chem. Soc. 1966, 88, 2520-2525;
97. (c) P. J. Smith, K. C. Westaway in Uses of Isotopically Labelled Amino, Quaternary Ammonium and Nitro Compounds, The Chemistry of Amino, Nitroso and Nitro Compounds and their Derivatives (Ed.: S. Patai), Wiley, 1996; pp. 893-948, Supplement F2;
98. N2 Processes; Isotopes in Organic Chemistry, Vol.7, Secondary and Solvent Isotope Effects (Eds.: E. Buncel, C. C. Lee), Elsevier, 1987, pp. 275-392;
99. e) I. Lee, Chem. Soc. Rev. 1995, 24, 223-229;
100. f) I. Mihel, J. O. Knippe, J. K. Coward, R. L. Schowen, J. Am. Chem. Soc. 1979, 101, 4349-4351.
101. See, for example: a) G. Cardillo, L. Gentilucci, M. Gianotti, A. Tolomelli, Tetrahedron 2001, 57, 2807-2812;
102. b) G. Cardillo, L. Gentilucci, G. P. Mohr, Eur. J. Org. Chem. 2001, 3545-3551;
103. (c) G. Cardillo, L. Gentilucci, A. Tolomelli, Chem. Commun. 1999, 167-168;
104. (d) G. Cardillo, L. Gentilucci, A. Tolomelli, C Tomasini, Tetrahedron Lett. 1997, 38, 6953-6956;
105. e) G. Cardillo, L. Gentilucci, A. Tolomelli, Aldrichimica Acta 2003, 36, 39-50;
106. f) V.-K. Lee, H.-J. Ha, Aldrichimica Acta 2003, 36, 57-63.
107. a) K. Hori, T. Nishiguchi, A. Nabeya, J. Org. Chem. 1997, 62, 3081-3088;
108. b)D. Ferraris, W. J. Drury III, C Cox, T. Lectka, J. Org. Chem. 1998, 65, 4508-4509.
109. See, for example: a) A. Imamura, H. Ando, H. Ishida, M. Kiso, Org. Lett. 2005, 7, 4415-4418;
110. b) J.-S. Park, Y. Akiyama, F. M. Winnik, K. Kataoka, Macromolecules 2004, 37, 6786-6792;
111. (c) B. S. Orlek, Synlett 1996, 477-478;
112. (d) M. J. Fazio, J. Org. Chem. 1984, 49, 4889-4893;
113. e) H. L. Wehrmeister, J. Org. Chem. 1963, 28, 2587-2588.
114. F. J. Lakner, L. P. Hager, Tetrahedron: Asymmetry 1997, 8, 3547-3550.
115. a) For a very recent report on the isolation and reactivity of aziridinium salts, in which the rearrangement to the oxazolinium cation was proposed as a mechanistic pathway, see: H. A. Song, M. Dadwald, Y. Lee, E. Mick, H.-S. Chong, Angew. Chem. 2009, 121, 1354-1356;
116. Angew. Chem. Int. Ed. 2009, 48, 1328-1330;
117. b) Y. Kim, H.-J. Ha, S. Y. Yun, W. K. Lee, Chem. Commun. 2008, 4363-4365.
118. a) A. Bouyacoub, Y. Jean, F Volatron, J. Mol. Struct. 1996, 371, 51-57;
119. b) M. A. Silva, J. M. Goodman, Tetrahedron Lett. 2005, 46, 2067-2069;
120. (c) M. D'hooghe, V. Van Speybroeck, M. Waroquier, N. De Kimpe, Chem. Commun. 2006, 1554-1556;
121. (d) M. D'hooghe, V. Van Speybroeck, A. Van Nieuwenhove, M. Waroquier, N. De Kimpe, J. Org. Chem. 2007, 72, 4733-4740.
122. a) C. Lee, W. Yang, R. Parr, Phys. Rev. B 1988, 37, 785-789;
123. b) A. D. Becke, J. Chem. Phys. 1993, 98, 5648-5652.
124. Gaussian 03, Revision C0l, M.J. Frisch, G.W. Trucks, H.B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, J. A. Montgomery, Jr., T. Vreven, K. N. Kudin, J. C. Burant, J. M. Millam, S. S. Iyengar, J. Tomasi, V. Barone, B. Mennucci, M. Cossi, G. Scalmani, N. Rega, G. A. Petersson, H. Nakatsuji, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, M. Klene, X. Li, J. E. Knox, H. P. Hratchian, J. B. Cross, C. Adamo, J. Jaramillo, R. Gomperts, R. E. Stratmann, O. Yazyev, A. J. Austin, R. Cammi, C. Pomelli, J. W. Ochterski, P. Y. Ayala, K. Morokuma, G. A. Voth, P. Salvador, J. J. Dannenberg, V. G. Zakrzewski, S. Dapprich, A. D. Daniels, M. C. Strain, O. Farkas, D. K. Malick, A. D. Rabuck, K. Raghavachari, J. B. Foresman, J. V. Ortiz, Q. Cui, A. G. Baboul, S. Clifford, J. Cioslowski, B. B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, I. Komaromi, R. L. Martin, D. J. Fox, T. Keith, M. A. Al-Laham, C. Y. Peng, A. Nanayakkara, M. Challacombe, P. M. W. Gill, B. Johnson, W. Chen, M.W. Wong, C. Gonzalez, J. A. Pople, Gaussian, Inc., Wallingford CT, 2004.
125. S. F. Boys, F. Bernardi, J. Mol. Biol. Mol. Phys. 1970, 19, 553.
126. a) C. W. Bauschlicher, Jr., Chem. Phys. Leu. 1995, 246, 40- 44;
127. b) A. P. Scott, L. Radom, J. Phys. Chem. 1996, 100, 16502-16513;
128. (c) J. P. Merrick, D. Moran, L. Radom, J. Phys. Chem. A 2007, 111, 11683-11700.
129. a) C Gonzalez, H. B. Schlegel, J. Chem. Phys. 1989, 90, 2154-2161;
130. b) C. Gonzalez, H. B. Schlegel, J. Chem. Phys. 1990, 92-93, 5523-5527.
131. a) M. Cossi, V. Barone, B. Mennucci, J. Tomasi, Chem. Phys. Leu. 1998, 286, 253-260;
132. b) J. Tomasi, B. Mennucci, E. Canees, J. Mol. Struct. 1999, 474-515, 211-226;
133. (c) M. Cossi, G. Scalmani, N. Rega, V. Barone, J. Chem. Phys. 2002, 117, 43-54, and references cited therein;
134. (d) J. Tomasi, B. Mennucci, R. Cammi, Chem. Rev. 2005, 105, 2999-3093.
135. G. M. Sheldrick, SHELXL97. Program for the refinement of crystal structures, University of Göttingen, Germany, 1997.