Diastereoselectivity control in formal nucleophilic substitution of bromocyclopropanes with oxygen- and sulfur-based nucleophiles

Journal of Organic Chemistry

Volumn 76, Issue 10, 2011, Pages 3968-3986

  Banning, Joseph E ^a   Prosser, Anthony R ^a   Alnasleh, Bassam K ^a   Smarker, Jason ^a   Rubina, Marina ^a   Rubin, Michael ^a  

^a UNIVERSITY OF KANSAS   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BULKY SUBSTITUENTS; CARBOXAMIDES; CYCLOPROPENES; DIASTEREO-SELECTIVITY; DIASTEREOSELECTIVE ADDITIONS; EPIMERIZATION; IN-SITU FORMATIONS; NUCLEOPHILIC SUBSTITUTIONS; STERIC CONTROL;

CARBOXYLATION; NUCLEOPHILES; OXYGEN; PROPYLENE; REACTION INTERMEDIATES; SULFUR;

STEREOSELECTIVITY;

AMIDE; CARBON; CARBOXYLIC ACID; CYCLOPROPANE DERIVATIVE; ESTER; FUNCTIONAL GROUP; NUCLEOPHILE; OXIDE; OXYGEN; SULFUR; THIOPHENOL DERIVATIVE;

ADDITION REACTION; ARTICLE; CHEMICAL BOND; CHEMICAL REACTION; EPIMERIZATION; STEREOCHEMISTRY; SUBSTITUTION REACTION; THERMODYNAMICS;

CYCLOPROPANES; OXYGEN; STEREOISOMERISM; SUBSTRATE SPECIFICITY; SULFUR;

EID: 79956096943     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo200368a     Document Type: Article

References (110)

1. For reviews, see: Salaün, J.; Baird, M. S. Curr. Med. Chem. 1995, 2, 511
2. Salaün, J. Zh. Org. Khim. 1997, 33, 806
3. For recent examples see: Zou, J.; Wu, J.; Liu, S.-Z.; Zhao, W.-M. Helv. Chim. Acta 2010, 93, 1812
4. Li, S.; Chiu, G.; Pulito, V. L.; Liu, J.; Connolly, P. J.; Middleton, S. A. Med. Chem. 2009, 5, 15
5. Chandru, H.; Sharada, A. C.; Bettadaiah, B. K.; Ananda Kumar, C. S.; Rangappa, K. S.; Sunila; Jayashree, K. Bioorg. Med. Chem. 2007, 15, 7696
6. Josien, H.; Bara, T.; Rajagopalan, M.; Asberom, T.; Clader, J. W.; Favreau, L.; Greenlee, W. J.; Hyde, L. A.; Nomeir, A. A.; Parker, E. M.; Pissarnitski, D. A.; Song, L.; Wong, G. T.; Zhang, L.; Zhang, Q.; Zhao, Z. Bioorg. Med. Chem. Lett. 2007, 17, 5330
7. Goel, G.; Makkar, H. P. S.; Francis, G.; Becker, K. Int. J. Toxicol. 2007, 26, 279
8. Chang, Z.-F.; Lee, H.-H. J. Biomed. Sci. 2006, 13, 173
9. Hezareh, M. Drug News Perspect. 2005, 18, 496
10. See, for example: Dortch-Carnes, J.; Potter, D. E. CNS Drug Rev. 2005, 11, 195
11. Amarante, L. H.; Alves, D. P.; Duarte, I. D. G. Eur. J. Pharmacol. 2004, 494, 155
12. Potter, D. E.; Russell, K. R. M.; Manhiani, M. J. Pharmacol. Exp. Ther. 2004, 309, 548
13. See, for example: Bellesi, M.; Conti, F. Neuropsychopharmacology 2010, 35, 1253
14. Sidhpura, N.; Weiss, F.; Martin-Fardon, R. Biol. Psychiatry 2010, 67, 804
15. Imre, G. CNS Drug Rev. 2007, 13, 444
16. For seminal reviews, see: Bekish, A. V.; Prokhorevich, K. N.; Pritytskaya, T. S.; Kulinkovich, O. G. Pol. J. Chem. 2006, 80, 549
17. Salaun, J. Chem. Rev. 2005, 105, 285
18. Kulinkovich, O. G. Chem. Rev. 2003, 103, 2597
19. Gibson, D. H.; DePuy, C. H. Chem. Rev. 1974, 74, 605
20. DePuy, C. H. Acc. Chem. Res. 1968, 1, 33
21. For recent examples see: Liu, P.; Sirois, L. E.; Cheong, P. H.-Y.; Yu, Z.-X.; Hartung, I. V.; Rieck, H.; Wender, P. A.; Houk, K. N. J. Am. Chem. Soc. 2010, 132, 10127
22. Wang, Y.-F.; Chiba, S. J. Am. Chem. Soc. 2009, 131, 12570
23. Kleinbeck, F.; Toste, F. D. J. Am. Chem. Soc. 2009, 131, 9178
24. Kim, K.; Cha, J. K. Angew. Chem., Int. Ed. 2009, 48, 5334
25. Chiba, S.; Kitamura, M.; Narasaka, K. J. Am. Chem. Soc. 2006, 128, 6931
26. Kingsbury, J. S.; Corey, E. J. J. Am. Chem. Soc. 2005, 127, 13813
27. See, for recent examples: Kang, J. Y.; Connell, B. T. J. Am. Chem. Soc. 2010, 132, 7826
28. Fortner, K. C.; Kato, D.; Tanaka, Y.; Shair, M. D. J. Am. Chem. Soc. 2010, 132, 275
29. Ho, C.-M.; Zhang, J.-L.; Zhou, C.-Y.; Chan, O.-Y.; Yan, J. J.; Zhang, F.-Y.; Huang, J.-S.; Che, C.-M. J. Am. Chem. Soc. 2010, 132, 1886
30. Ganesh, N. V.; Raghothama, S.; Sonti, R.; Jayaraman, N. J. Org. Chem. 2010, 75, 215
31. Brand, C.; Rauch, G.; Zanoni, M.; Dittrich, B.; Werz, D. B. J. Org. Chem. 2009, 74, 8779
32. Gharpure, S. J.; Shukla, M. K.; Vijayasree, U. Org. Lett. 2009, 11, 5466
33. Wang, Y.-F.; Chiba, S. J. Am. Chem. Soc. 2009, 131, 12570
34. Fischer, E. O.; Dötz, K. H. Chem. Ber. 1970, 103, 1273
35. Dötz, K. H.; Fischer, E. O. Chem. Ber. 1972, 105, 1356
36. Cooke, M. D.; Fischer, E. O. J. Organomet. Chem. 1973, 56, 279
37. Wienand, A.; Reissig, H.-U. Organometallics 1990, 9, 3133
38. See, for recent examples: Moss, R. A.; Zhang, M.; Krogh-Jespersen, K. Org. Lett. 2010, 12, 3476
39. Fernandez-Rodriguez, M. A.; Andina, F.; Garcia-Garcia, P.; Rocaboy, C.; Aguilar, E. Organometallics 2009, 28, 361
40. Aznar, F.; Fananas-Mastral, M.; Alonso, J.; Fananas, F. J. Chem. - Eur. J. 2008, 14, 325
41. Barluenga, J.; Suero, M. G.; Perez-Sanchez, I.; Florez, J. J. Am. Chem. Soc. 2008, 130, 2708
42. See, for recent examples: Kim, K.; Cha, J. K. Angew. Chem., Int. Ed. 2009, 48, 5334
43. Josien, H.; Bara, T.; Rajagopalan, M.; Clader, J. W.; Greenlee, W. J.; Favreau, L.; Hyde, L. A.; Nomeir, A. A.; Parker, E. M.; Song, L.; Zhang, L.; Zhang, Q. Bioorg. Med. Chem. Lett. 2009, 19, 6032
44. See, for example: Kozhushkov, S. I.; Spaeth, T.; Kosa, M.; Apeloig, Y.; Yufit, D. S.; de Meijere, A. Eur. J. Org. Chem. 2003, 4234
45. Hollingworth, G. J.; Dinnell, K.; Dickinson, L. C.; Elliott, J. M.; Kulagowski, J. J.; Swain, C. J.; Thomson, C. G. Tetrahedron Lett. 1999, 40, 2633
46. Loeppky, R. N.; Elomari, S. J. Org. Chem. 2000, 65, 96
47. See, for example: Jonczyk, A.; Kmiotek-Skarzynska, I. Synthesis 1992, 985
48. Jonczyk, A.; Kmiotek-Skarzynska, I. J. Org. Chem. 1989, 54, 2756
49. Shields, T. C.; Shoulders, B. A.; Krause, J. F.; Osborn, C. L.; Gardner, P. D. J. Am. Chem. Soc. 1965, 87, 3026
50. Jonczyk, A.; Kocmierowski, T.; Zdrojewski, T. New J. Chem. 2003, 27, 295
51. Ishihara, T.; Kudaka, T.; Ando, T. Tetrahedron Lett. 1984, 25, 4765
52. Parham, W. E.; McKown, W. D.; Nelson, V.; Kajigaeshi, S.; Ishikawa, N. J. Org. Chem. 1973, 38, 1361
53. Taylor, E. C.; Hu, B. Synth. Commun. 1996, 26, 1041
54. See for example: Chiu, G.; Li, S.; Connolly, P. J.; Pulito, V.; Liu, J.; Middleton, S. A. Bioorg. Med. Chem. Lett. 2007, 17, 3930
55. van Tilburg, E. W.; van der Klein, P. A. M.; von Frijtag Drabbe Kuenzel, J. K.; de Groote, M.; Stannek, C.; Lorenzen, A.; Ijzerman, A. P. J. Med. Chem. 2001, 44, 2966
56. Müller, P.; Pautex, N. Helv. Chim. Acta 1988, 71, 1630
57. Yamaguchi, H.; Okamoto, T. Chem. Pharm. Bull. 1975, 23, 2907
58. Weyerstahl, P.; Marschall-Weyerstahl, H.; Huelskaemper, L. Chem. Ber. 1986, 119, 1477
59. For nonselective formal substitution of cyclopropyl halides with sulfur-based nucleophiles, suggested to operate via cyclopropene intermediate, see: Jonczyk, A.; Kocmierowski, T.; Zdrojewski, T. New J. Chem. 2003, 27, 295
60. Schaumann, E.; Friese, C.; Adiwidjaja, G. Tetrahedron 1989, 45, 3163
61. Fedorynski, M.; Dybowska, A.; Jonczyk, A. Synthesis 1988, 549
62. Hirao, T.; Harano, Y.; Yamana, Y.; Hamada, Y.; Nagata, S.; Agawa, T. Bull. Chem. Soc. Jpn. 1986, 59, 1341
63. Mueller, P.; Huong, C. N. T.; Pfyffer, J. Helv. Chim. Acta 1986, 69, 855
64. For related elimination-addition processes involving methylenecyclopropane intermediate, see: Bagutski, V.; de Meijere, A. Adv. Synth. Catal. 2007, 349, 1247 For cyclopropenylium ion intermediate see: Lee, G.-A.; Chen, K. C. Org. Lett. 2008, 10, 1843
65. For examples on processes in which selectivity is achieved in caged polycyclic structure and caused by excessive rigidity, see: Nikitina, L. E.; Plemenkov, V. V.; Startseva, V. A.; Dieva, S. A.; Baird, M. S. Sulfur Lett. 2001, 24, 223
66. Startseva, V. A.; Nikitina, L. E.; Plemenkov, V. V. Russ. J. Gen. Chem. 2000, 70, 1760
67. Mueller, P.; Bernardinelli, G.; Godoy-Nguyen, T.; Huong, C. Helv. Chim. Acta 1989, 72, 1627
68. Part of these studies was preliminary communicated; see: Alnasleh, B. K.; Sherrill, W. M.; Rubina, M.; Banning, J.; Rubin, M. J. Am. Chem. Soc. 2009, 131, 6906
69. Banning, J. E.; Prosser, A. R.; Rubin, M. Org. Lett. 2010, 12, 1488
70. Wiberg, K. B.; Barnes, R. K.; Albin, J. J. Am. Chem. Soc. 1957, 79, 4994
71. These conditions proved optimal for generation of 3,3-disubstituted cyclopropenes, see ref 24b.
72. For previous examples of low stability of cyclopropene-3-carboxylic esters toward nucleophilic attack, see: Kudrevich, S. V.; Rubin, M. A.; Tarabaeva, O. G.; Surmina, L. S.; Baird, M. S.; Bolesov, I. G. Zh. Org. Khim. 1994, 30, 945
73. Sherrill, W. M.; Kim, R.; Rubin, M. Synthesis 2009, 1477
74. Kim, R.; Sherrill, W. M.; Rubin, M. Tetrahedron 2010, 66, 4947
75. For a similar chemoselectivity in addition of amino alcohols to cyclopropenes, see: Shavrin, K. N.; Gvozdev, V. D.; Nefedov, O. M. Russ. Chem. Bull. 2008, 57, 2117
76. For direct transition metal-catalyzed addition of terminal alkynes across the double bond of cyclopropenes, see: Yin, J.; Chisholm, J. D. Chem. Commun. 2006, 632
77. Teganalia, A.; Le Jeune, K.; Giordano, L.; Buono, G. Org. Lett. 2011, 13, 636
78. 5Br, see: Chandru, H.; Sharada, A. C.; Bettadaiah, B. K.; Ananda, K., C. S.; Rangappa, K. S.; Jayashree, K. Bioorg. Med. Chem. 2007, 15, 7696
79. Corbett, J. W.; Rauckhorst, M. R.; Qian, F.; Hoffman, R. L.; Knauer, C. S.; Fitzgerald, L. W. Bioorg. Med. Chem. Lett. 2007, 17, 6250-6256
80. The ?(-)-values used are derived from Swain-Lupton parameters adopted from: Swain, C. G.; Lupton, E. C., Jr. J. Am. Chem. Soc. 1968, 90, 4328
81. Williams, S. G.; Norrington, F. E. J. Am. Chem. Soc. 1976, 98, 508
82. Sherrill, W. M.; Kim, R.; Rubin, M. Tetrahedron 2008, 64, 8610-8617 and references cited therein.
83. Rubin, M.; Gevorgyan, V. Synthesis 2004, 796 See also ref 24a.
84. For recent reviews, see: Marek, I.; Simaan, S.; Marasawa, A. Angew. Chem., Int. Ed. 2007, 46, 7364
85. Rubin, M.; Rubina, M.; Gevorgyan, V. Chem. Rev. 2007, 107, 3117
86. Rubin, M.; Rubina, M.; Gevorgyan, V. Synthesis 2006, 1221
87. Fox, J. M.; Yan, N. Curr. Org. Chem. 2005, 9, 719
88. Nakamura, M.; Isobe, H.; Nakamura, E. Chem. Rev. 2003, 103, 1295
89. For hydrometalations and dimetalations, see: Rubina, M.; Rubin, M.; Gevorgyan, V. J. Am. Chem. Soc. 2002, 124, 11566
90. Rubina, M.; Rubin, M.; Gevorgyan, V. J. Am. Chem. Soc. 2003, 125, 7198
91. Rubina, M.; Rubin, M.; Gevorgyan, V. J. Am. Chem. Soc. 2004, 126, 3688
92. Trofimov, A.; Rubina, M.; Rubin, M.; Gevorgyan, V. J. Org. Chem. 2007, 72, 8910 For hydrophosphorylation and hydrophosphilylation, see: Alnasleh, B. K.; Sherrill, W. M.; Rubin, M. Org. Lett. 2008, 10, 3231 For hydroformylation, see: Sherrill, W. M.; Rubin, M. J. Am. Chem. Soc. 2008, 130, 13804 For hydroacylation, see: Phan, D. H. T.; Kou, K. G. M.; Dong, V. M. J. Am. Chem. Soc. 2010, 132, 16354 For carbometalations, see: Nakamura, M.; Hirai, A.; Nakamura, E. J. Am. Chem. Soc. 2000, 122, 978
93. Nakamura, E.; Yoshikai, N. J. Org. Chem. 2010, 75, 6061
94. Liao, L.; Fox, J. M. J. Am. Chem. Soc. 2002, 124, 14322
95. Liu, X.; Fox, J. M. J. Am. Chem. Soc. 2006, 128, 5600
96. Yan, N.; Liu, X.; Fox, J. M. J. Org. Chem. 2008, 73, 563
97. Tarwade, V.; Liu, X.; Yan, N.; Fox, J. M. J. Am. Chem. Soc. 2009, 131, 5382
98. Bloch, R.; Denis, J. M. Angew. Chem. 1980, 92, 969
99. For removal of benzyl protection from cylopropanols, see: Guillerm, G.; Muzard, M.; Glapski, C. Bioorg. Med. Chem. Lett. 2004, 14, 5799
100. Diez, D.; Garcia, P.; Marcos, I. S.; Garrido, N. M.; Basabe, P.; Urones, J. G. Synthesis 2003, 53
101. Prosser, A. R.; Banning, J. E.; Rubina, M.; Rubin, M. Org. Lett. 2010, 12, 3968
102. Wagner, B. J.; Doi, J. T.; Musker, W. K. J. Org. Chem. 1990, 55, 4156
103. Polshettiwar, V.; Varma, R. S. Tetrahedron 2010, 66, 1091
104. Schade, W.; Beger, J.; Jacobi, R.; Neumann, R. J. Prakt. Chem. 1983, 325, 364
105. Yadav, J. S.; Reddy, B. V. S.; Basak, A. K.; Narsaiah, A. V. Chem. Lett. 2003, 32, 988
106. Artyushin, O. I.; Petrovskii, P. V.; Mastryukova, T. A.; Kabachnik, M. I. Izv. Akad. Nauk SSSR, Ser. Khim. 1991, 2154
107. Yurev, Yu. K.; Novitskii, K. Yu.; Bolesov, I. G. Zh. Obshch. Khim. 1959, 29, 2951
108. Voelkel, A.; Krysztafkiewicz, A. Powder Technol. 1998, 95, 103
109. Snyder, H. R.; Stewart, J. M.; Ziegler, J. B. J. Am. Chem. Soc. 1947, 69, 2672
110. Schmidt, K.; ONeal, S.; Chan, T. C.; Alexis, C. P.; Uribe, J. M.; Lossener, K.; Gutierrez, C. G. Tetrahedron Lett. 1989, 30, 7301