β-siloxy-α-haloketones through highly diastereoselective single and double mukaiyama aldol reactions

Chemistry - A European Journal

Volumn 19, Issue 12, 2013, Pages 3842-3845

  Saadi, Jakub ^a   Yamamoto, Hisashi ^a  

^a UNIVERSITY OF CHICAGO   (United States)

Author keywords

aldol reactions; cascade reactions; diastereoselectivity; haloketones; polyketides

Indexed keywords

ALDOL REACTIONS; CASCADE REACTIONS; DIASTEREO-SELECTIVITY; HALOKETONES; POLYKETIDES;

KETONES; STEREOSELECTIVITY;

CHEMICAL REACTIONS;

3-HYDROXYBUTANAL; ALDEHYDE; ALDOL; HALOGENATED HYDROCARBON; KETONE; ORGANOSILICON DERIVATIVE; POLYKETIDE;

ARTICLE; CHEMISTRY; STEREOISOMERISM; SYNTHESIS;

ALDEHYDES; HYDROCARBONS, HALOGENATED; KETONES; ORGANOSILICON COMPOUNDS; POLYKETIDES; STEREOISOMERISM;

EID: 84874989384     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.201204493     Document Type: Article

References (96)

1. K. Naumann, J. Prakt. Chem. 1999, 341, 417-435
2. C. Isanbor, D. O'Hagan, J. Fluorine Chem. 2006, 127, 303-319
3. K. L. Kirk, J. Fluorine Chem. 2006, 127, 1013-1029
4. P. Jeschke, Pest Manage. Sci. 2010, 66, 10-27
5. M. Z. Hernandes, S. M. T. Cavalcanti, D. R. M. Moreira, W. Filgueira de Azevedo Jr., A. C. L. Leite, Curr. Drug Targets 2010, 11, 303-314.
6. G. W. Gribble, Prog. Chem. Org. Nat. Prod. 1996, 68, 1-423
7. G. W. Gribble, J. Chem. Educ. 2004, 81, 1441-1449
8. G. W. Gribble, Prog. Chem. Org. Nat. Prod. 2010, 91, 1-613, and references therein.
9. C. Nilewski, R. W. Geisser, E. M. Carreira, Nature 2009, 457, 573-577
10. C. Nilewski, R. W. Geisser, E. M. Carreira, J. Am. Chem. Soc. 2009, 131, 15866-15876
11. D. K. Bedke, G. M. Shibuya, A. Pereira, W. H. Gerwick, T. H. Haines, C. D. Vanderwal, J. Am. Chem. Soc. 2009, 131, 7570-7572
12. D. K. Bedke, G. M. Shibuya, A. R. Pereira, W. H. Gerwick, C. D. Vanderwal, J. Am. Chem. Soc. 2010, 132, 2542-2543
13. T. Yoshimitsu, N. Fukumoto, R. Nakatani, N. Kojima, T. Tanaka, J. Org. Chem. 2010, 75, 5425-5437
14. T. Umezawa, M. Shibata, K. Kaneko, T. Okino, F. Matsuda, Org. Lett. 2011, 13, 904-907
15. T. Yoshimitsu, R. Nakatani, A. Kobayashi, T. Tanaka, Org. Lett. 2011, 13, 908-911
16. D. K. Bedke, C. D. Vanderwal, Nat. Prod. Rep. 2011, 28, 15-25
17. K. C. Nicolaou, N. L. Simmons, Y. Ying, P. M. Heretsch, J. S. Chen, J. Am. Chem. Soc. 2011, 133, 8134-8137
18. C. Nilewski, N. R. Deprez, T. C. Fessard, D. B. Li, R. W. Geisser, E. M. Carreira, Angew. Chem. 2011, 123, 8087-8091
19. Angew. Chem. Int. Ed. 2011, 50, 7940-7943
20. C. Nilewski, E. M. Carreira, Eur. J. Org. Chem. 2012, 1685-1698.
21. S. D. Rychnovsky, Chem. Rev. 1995, 95, 2021-2040
22. A. M. P. Koskinen, K. Karisalmi, Chem. Soc. Rev. 2005, 34, 677-690
23. G. M. Cragg, P. G. Grothaus, D. J. Newman, Chem. Rev. 2009, 109, 3012-3043.
24. T. Mukaiyama, T. Haga, N. Iwasawa, Chem. Lett. 1982, 1601-1604
25. T. Mukaiyama, N. Iwasawa, R. W. Stevens, T. Haga, Tetrahedron 1984, 40, 1381-1390
26. E. Öhler, H.-S. Kang, E. Zbiral, Chem. Ber. 1988, 121, 299-308
27. D. Vo, K. C. Agarwal, E. E. Knaus, T. M. Allen, R. Fathi-Afshar, Eur. J. Med. Chem. 1988, 23, 39-44
28. I. Shibata, H. Yamasaki, A. Baba, H. Matsuda, Synlett 1990, 490-492
29. I. Shibata, H. Yamasaki, A. Baba, H. Matsuda, J. Org. Chem. 1992, 57, 6909-6914
30. D. Enders, R. Hett, Synlett 1998, 961-962
31. C. Palomo, M. Oiarbide, A. K. Sharma, M. C. González-Rego, A. Linden, J. M. García, A. González, J. Org. Chem. 2000, 65, 9007-9012
32. Z. Rapi, T. Szabõ, G. Keglevich, Á. Szöllösy, L. Drahos, P. Bakõ, Tetrahedron: Asymmetry 2011, 22, 1189-1196.
33. T. Mukaiyama, I. Shiina, H. Iwadare, M. Saitoh, T. Nishimura, N. Ohkawa, H. Sakoh, K. Nishimura, Y. Tani, M. Hasegawa, K. Yamada, K. Saitoh, Chem. Eur. J. 1999, 5, 121-161
34. S. C. Sinha, S. Dutta, J. Sun, Tetrahedron Lett. 2000, 41, 8243-8246
35. S. R. V. Kandula, P. Kumar, Tetrahedron Lett. 2003, 44, 6149-6151.
36. B. C. Ranu, T. Mandal, Tetrahedron Lett. 2006, 47, 2859-2861
37. J. Nebot, P. Romea, F. Urpí, J. Org. Chem. 2009, 74, 7518-7521
38. S. B. Sapkal, K. F. Shelke, B. B. Shingate, M. S. Shingare, Chin. Chem. Lett. 2010, 21, 1439-1442.
39. J. Nebot, P. Romea, F. Urpí, Org. Biomol. Chem. 2012, 10, 6395-6403.
40. H. Sasai, Y. Kirio, M. Shibasaki, J. Org. Chem. 1990, 55, 5306-5308
41. H. Sasai, T. Suzuki, S. Arai, T. Arai, M. Shibasaki, J. Am. Chem. Soc. 1992, 114, 4418-4420
42. H. C. Brown, M.-F. Zou, P. V. Ramachandran, Tetrahedron Lett. 1999, 40, 7875-7877
43. Y. Yoshida, N. Matsumoto, R. Hamasaki, Y. Tanabe, Tetrahedron Lett. 1999, 40, 4227-4230
44. Y. Tanabe, N. Matsumoto, T. Higashi, T. Misaki, T. Itoh, M. Yamamoto, K. Mitarai, Y. Nishii, Tetrahedron 2002, 58, 8269-8280
45. C. Peppe, R. P. das Chagas, R. Pavão, Synlett 2006, 605-609.
46. M. C. Pirrung, J. R. Hwu, Tetrahedron Lett. 1983, 24, 565-568
47. J. T. Welch, K. W. Seper, Tetrahedron Lett. 1984, 25, 5247-5250
48. H. Hata, T. Kobayashi, H. Amii, K. Uneyama, J. T. Welch, Tetrahedron Lett. 2002, 43, 6099-6102
49. D.-Y. Zhou, U.-Y. Chen, Chin. J. Chem. 2004, 22, 953-957.
50. D. Hebel, S. Rozen, J. Org. Chem. 1987, 52, 2588-2590
51. D. D. DesMarteau, Z.-Q. Xu, M. Witz, J. Org. Chem. 1992, 57, 629-635
52. H. Masuda, K. Takase, M. Nishio, A. Hasegawa, Y. Nishiyama, Y. Ishii, J. Org. Chem. 1994, 59, 5550-5555
53. T. Sato, S. Yonemochi, Tetrahedron 1994, 50, 7375-7384
54. S. C. Roy, C. Guin, K. K. Rana, G. Maiti, Synlett 2001, 226-227
55. D. Urankar, I. Rutar, B. Modec, D. Dolenc, Eur. J. Org. Chem. 2005, 2349-2353
56. J. N. Moorthy, K. Senapati, S. Kumar, J. Org. Chem. 2009, 74, 6287-6290.
57. T. Hoffmann, G. Zhong, B. List, D. Shabat, J. Anderson, S. Gramatikova, R. A. Lerner, C. F. Barbas III, J. Am. Chem. Soc. 1998, 120, 2768-2779
58. V. Maggiotti, S. Bahmanyar, M. Reiter, M. Resmini, K. N. Houk, V. Gouverneur, Tetrahedron 2004, 60, 619-632.
59. T. Kitazume, K. Tamura, Z. Jiang, N. Miyake, I. Kawasaki, J. Fluorine Chem. 2002, 115, 49-53
60. T. Kitazume, Z. Jiang, K. Kasai, Y. Mihara, M. Suzuki, J. Fluorine Chem. 2003, 121, 205-212
61. G. Zhong, J. Fana, C. F. Barbas III, Tetrahedron Lett. 2004, 45, 5681-5684
62. L. He, Z. Tang, L.-F. Cun, A.-Q. Mi, Y.-Z. Jiang, L.-Z. Gong, Tetrahedron 2006, 62, 346-351
63. G. Guillena, M. d. C. Hita, C. Nájera, Tetrahedron: Asymmetry 2007, 18, 1272-1277
64. X.-H. Chen, S.-W. Luo, Z. Tang, L.-F. Cun, A.-Q. Mi, Y.-Z. Jiang, L.-Z. Gong, Chem. Eur. J. 2007, 13, 689-701
65. X.-Y. Xu, Y.-Z. Wang, L.-F. Cuna, L.-Z. Gong, Tetrahedron: Asymmetry 2007, 18, 237-242
66. X.-Y. Xu, Y.-Z. Wang, L.-Z. Gong, Org. Lett. 2007, 9, 4247-4249
67. A. Russo, G. Botta, A. Lattanzi, Tetrahedron 2007, 63, 11886-11892
68. G. Guillena, M. d. C. Hita, C. Nájera, S. F. Viõzquez, J. Org. Chem. 2008, 73, 5933-5943
69. K. Sato, M. Kuriyama, R. Shimazawa, T. Morimoto, K. Kakiuchi, R. Shirai, Tetrahedron Lett. 2008, 49, 2402-2406
70. Á. Martínez-Castañeda, B. Poladura, H. Rodríguez-Solla, C. Concellõn, V. del Amo, Chem. Eur. J. 2012, 18, 5188-5190
71. A. Umehara, T. Kanemitsu, K. Nagata, T. Itoh, Synlett 2012, 23, 453-457.
72. M. B. Boxer, H. Yamamoto, J. Am. Chem. Soc. 2006, 128, 48-49
73. M. B. Boxer, H. Yamamoto, Nat. Protoc. 2006, 1, 2434-2438
74. M. B. Boxer, H. Yamamoto, J. Am. Chem. Soc. 2007, 129, 2762-2763
75. M. B. Boxer, H. Yamamoto, Org. Lett. 2008, 10, 453-455
76. M. B. Boxer, M. Akakura, H. Yamamoto, J. Am. Chem. Soc. 2008, 130, 1580-1582
77. M. B. Boxer, B. J. Albert, H. Yamamoto, Aldrichimica Acta 2009, 42, 3-15
78. B. J. Albert, H. Yamamoto, Angew. Chem. 2010, 122, 2807-2809
79. Angew. Chem. Int. Ed. 2010, 49, 2747-2749
80. Y. Yamaoka, H. Yamamoto, J. Am. Chem. Soc. 2010, 132, 5354-5356
81. B. J. Albert, Y. Yamaoka, H. Yamamoto, Angew. Chem. 2011, 123, 2658-2660
82. Angew. Chem. Int. Ed. 2011, 50, 2610-2612
83. J. Saadi, M. Akakura, H. Yamamoto, J. Am. Chem. Soc. 2011, 133, 14248-14251
84. P. Brady, H. Yamamoto, Angew. Chem. 2012, 124, 1978-1982
85. Angew. Chem. Int. Ed. 2012, 51, 1942-1946.
86. H. Taguchi, H. Yamamoto, H. Nozaki, J. Am. Chem. Soc. 1974, 96, 3010-3011
87. M. Ma̧kosza, Rocz. Chem. 1972, 46, 533-534
88. M. Ma̧kosza, M. Wawrzyniewicz, Tetrahedron Lett. 1969, 10, 4659-4662
89. G. K. S. Prakash, J. Hu, G. A. Olah, J. Fluorine Chem. 2001, 112, 123.
90. Nucleophilic additions to α-haloaldehydes
91. V. J. Cee, C. J. Cramer, D. A. Evans, J. Am. Chem. Soc. 2006, 128, 2920-2930
92. B. Kang, R. Britton, Org. Lett. 2007, 9, 5083-5086
93. S. Díaz-Oltra, M. Carda, J. Murga, E. Falomir, J. A. Marco, Chem. Eur. J. 2008, 14, 9240-9254
94. M. Shinoyama, S. Shirokawa, A. Nakazaki, S. Kobayashi, Org. Lett. 2009, 11, 1277-1280
95. T. Borg, J. Danielsson, P. Somfai, Chem. Commun. 2010, 46, 1281-1283
96. T. Borg, J. Danielsson, M. Mohiti, P. Restorp, P. Somfai, Adv. Synth. Catal. 2011, 353, 2022-2036.