Pure and Applied Chemistry, 2007, Volume 79, No. 2, pp. 235-245, References

Pure Appl. Chem., 2007, Vol. 79, No. 2, pp. 235-245

http://dx.doi.org/10.1351/pac200779020235

Asymmetric catalysis in aqueous media

Shū Kobayashi

Graduate School of Pharmaceutical Sciences, The University of Tokyo, The HFRE Division, ERATO, Japan Science and Technology Agency (JST), Hongo, Bunkyo-ku, Tokyo 113-0033, Japan

References

1. (a). C.-J. Li, T.-H. Chan. Organic Reactions in Aqueous Media, John Wiley, New York (1997);
1. (b). Organic Synthesis in Water, P. A. Grieco (Ed.), Blackie Academic, London (1998);
1. (c). U. M. Lindstroem. Chem. Rev. 102, 2751 (2002); (http://dx.doi.org/10.1021/cr010122p)
1. (d). D. Sinou. Adv. Synth. Catal. 344, 237 (2002); (http://dx.doi.org/10.1002/1615-4169(200206)344:3/4<221::AID-ADSC221>3.0.CO;2-N)
1. (e). C.-J. Li. Chem. Rev. 105, 3095 (2005). (http://dx.doi.org/10.1021/cr030009u)
2. (a). D. Schinzer (Ed.). Selectivities in Lewis Acid Promoted Reactions, Kluwer Academic, Dordrecht (1989);
2. (b). H. Yamamoto (Ed.). Lewis Acids in Organic Synthesis, Wiley-VCH, Weinheim (2000);
2. (c). R. W. Hay. "Lewis acid catalysis and the reactions of coordinated ligands", in Comprehensive Coordination Chemistry, Vol. 6, G. Wilkinson, R. D. Gillard, J. A. McCleverty (Eds.), p. 411, Pergamon Press, Oxford (1987).
3. (a). S. Kobayashi. "Lanthanide triflate-catalyzed carbon-carbon bond-forming reactions in organic synthesis", in Lanthanides: Chemistry and Use in Organic Synthesis, S. Kobayashi (Ed.), p. 63, Springer, Heidelberg (1999); (http://dx.doi.org/10.1007/3-540-69801-9_2)
3. (b). S. Kobayashi. Eur. J. Org. Chem. 15 (1999); (http://dx.doi.org/10.1002/(SICI)1099-0690(199901)1999:1<15::AID-EJOC15>3.0.CO;2-B)
3. (c). S.Kobayashi. Synlett 689 (1994); (http://dx.doi.org/10.1055/s-1994-22976)
3. (d). S. Kobayashi, M. Sugiura, H. Kitagawa, W. W.-L. Lam. Chem. Rev. 102, 2227 (2002). (http://dx.doi.org/10.1021/cr010289i)
4. (a). S. Kobayashi. Chem. Lett. 2187 (1991); (http://dx.doi.org/10.1246/cl.1991.2187)
4. (b). S. Kobayashi, I. Hachiya. J. Org. Chem. 59, 3590 (1994). (http://dx.doi.org/10.1021/jo00092a017)
5. S. Kobayashi, S. Nagayama, T. Busujima. J. Am. Chem. Soc. 120, 8287 (1998). (http://dx.doi.org/10.1021/ja980715q)
6. (a). C. F. Baes Jr., R. E. Mesmer. The Hydrolysis of Cations, p. 129, John Wiley, New York (1976);
6. (b). K. B. Yatsimirksii, V. P. Vasil'ev. Instability Constants of Complex Compounds, Pergamon, New York (1960);
6. (c). Coordination Chemistry, ACS Monograph 174, Vol. 2, A. E. Martell (Ed.), American Chemical Society, Washington, DC (1978).
7. Fringuelli and coworkers reported use of Al(III), Ti(IV), and Sn(IV) as Lewis acids for epoxide opening reactions in acidic water whose pH is adjusted by adding H2SO4. F. Fringuelli, F. Pizzo, L. Vaccaro. J. Org. Chem. 66, 3554 (2001). (http://dx.doi.org/10.1021/jo015564f)
8. B. Cornils, W. A. Herrmann (Eds.). Aqueous-Phase Organometallic Catalysis, 2nd ed., Wiley-VCH, Weinheim (2004).
9. K. Manabe, S. Kobayashi. Chem. Eur. J. 8, 4094 (2002). (http://dx.doi.org/10.1002/1521-3765(20020916)8:18<4094::AID-CHEM4094>3.0.CO;2-G)
10. (a). S. Kobayashi, S. Nagayama, T. Busujima. Chem. Lett. 71 (1999); (http://dx.doi.org/10.1246/cl.1999.71)
10. (b). S.Nagayama, S. Kobayashi. J. Am. Chem. Soc. 122, 11531 (2000); (http://dx.doi.org/10.1021/ja001234l)
10. (c). S. Kobayashi, T. Hamada, K. Manabe. J. Am. Chem. Soc. 124, 5640 (2002); (http://dx.doi.org/10.1021/ja026094p)
10. (d). T. Hamada, K. Manabe, S. Ishikawa, S.Nagayama, M. Shiro, S. Kobayashi. J. Am. Chem. Soc. 125, 2989 (2003); (http://dx.doi.org/10.1021/ja028698z)
10. (e). T. Hamada, K.Manabe, S. Kobayashi. Angew. Chem., Int. Ed. 42, 3927 (2003); (http://dx.doi.org/10.1002/anie.200351778)
10. (f). T. Hamada, K. Manabe, S. Kobayashi. J. Am. Chem. Soc. 126, 7768 (2004); (http://dx.doi.org/10.1021/ja048607t)
10. (g). T. Hamada, K. Manabe, S. Kobayashi. Chem. Eur. J. 12, 1205 (2006); (http://dx.doi.org/10.1002/chem.200500673)
10. (h). S. Azoulay, K. Manabe, S. Kobayashi. Org. Lett. 7, 4593 (2005); (http://dx.doi.org/10.1021/ol051546z)
10. (i). C. Ogawa, S. Azoulay, S. Kobayashi. Heterocycles 66, 201 (2005).
11. (a). M. Fujii, Y. Sato, T.Aida, M. Yoshihara. Chem. Express 7, 309 (1992);
11. (b). R. Kuwano, H. Miyazaki, Y. Ito. Chem. Commun. 71 (1998); (http://dx.doi.org/10.1039/a706662g)
11. (c). H. Torii, M. Nakadai, K. Ishihara, S. Saito, H. Yamamoto. Angew. Chem., Int. Ed. 43, 1983 (2004). (http://dx.doi.org/10.1002/anie.200352724)
12. S. Kobayashi, K. Manabe, H. Ishitani, J. Matsuo. In Science of Synthesis, Houben-Weyl Methods of Molecular Transformation, Vol. 4, D. Bellus, S. V. Ley, R.Noyori, M. Regitz, E. Schaumann, I. Shinkai, E. J. Thomas, B. M. Trost (Eds.), p. 317, Georg Thieme Verlag, Stuttgart (2002).
13. (a). T. D. Machajewski, C.-H. Wong. Angew. Chem., Int. Ed. 39, 1352 (2000); (http://dx.doi.org/10.1002/(SICI)1521-3773(20000417)39:8<1352::AID-ANIE1352>3.0.CO;2-J)
13. (b). E. M. Carreira. Comprehensive Asymmetric Catalysis, Vol.3, E. N. Jacobsen, A. Pflatz, H. Yamamoto (Eds.), p. 998, Springer, Heidelberg (1999);
13. (c). S. G. Nelson. Tetrahedron: Asymmetry 9, 357 (1998). (http://dx.doi.org/10.1016/S0957-4166(97)00634-4)
14. Trioxane was used as a formaldehyde surrogate: T. Mukaiyama, K. Banno, K. Narasaka. J. Am. Chem. Soc. 96, 7503 (1974). (http://dx.doi.org/10.1021/ja00831a019)
15. (a). S. Kobayashi. Chem. Lett. 2187 (1991); (http://dx.doi.org/10.1246/cl.1991.2187)
15. (b). A. Lubineau, E. Meyer. Tetrahedron 44, 6065 (1988). (http://dx.doi.org/10.1016/S0040-4020(01)89795-7)
16. K. Manabe, S. Ishikawa, T. Hamada, S. Kobayashi. Tetrahedron 59, 10439 (2003). (http://dx.doi.org/10.1016/j.tet.2003.06.007)
17. N. Ozawa, M. Wadamoto, K. Ishihara, H. Yamamoto. Synlett 2219 (2003).
18. We performed the hydroxymethylation of 2 using 20 mol% of a Sc3+ source and 24 mol% of 1 in H2O/1,4-dioxane at 0 degC. As a result, Sc(OTf)3 and ScBr3 afforded almost the same results [Sc(OTf)3: 15 h, 86% yield, 84% ee; ScBr3: 22 h, 75% yield, 83% ee].
19. (a). D. A. Evans, Z. K. Sweeney, T. Rovis, J. S. Tedrow. J. Am. Chem. Soc. 123, 12095 (2001); (http://dx.doi.org/10.1021/ja011983i)
19. (b). D. A. Evans, K. A. Scheidt, K. R. Fandrick, H. W. Lam, J. Wu. J. Am. Chem. Soc. 125, 10780 (2003). (http://dx.doi.org/10.1021/ja036985c)
20. (a). P. L. Baliri, G. Catelani, R. Giori, E. Mastrorilli. Enantiomer 3, 357 (1998);
20. (b). H. Miyaoka, Y. Kajiwara, M. Hara, A. Suma, Y. Yamada. Tetrahedron: Asymmetry 10, 3189 (1999). (http://dx.doi.org/10.1016/S0957-4166(99)00304-3)
21. (a). H. Gaspard-Iloughmane, C. Le Roux. Eur. J. Org. Chem. 2517 (2004); (http://dx.doi.org/10.1002/ejoc.200300754)
21. (b). S. Repichet, A.Zwick, L. Vendier, C. Le Roux, J. Dubac. Tetrahedron Lett. 43, 993 (2002). (http://dx.doi.org/10.1016/S0040-4039(01)02307-3)
22. S. Repichet, A. Zwick, L. Vendier, C. Le Roux, J. Dubac. Tetrahedron Lett. 43, 993 (2002). (http://dx.doi.org/10.1016/S0040-4039(01)02307-3)
23. Sc(OTf)3 is a water-compatible Lewis acid, and it works well for hydroxymethylation even in the absence of a basic ligand. S. Kobayashi, I. Hachiya, H. Ishitani, M. Araki. Synlett 472 (1993).
24. S. Kobayashi, T. Ogino, H. Shimizu, S. Ishikawa, T. Hamada, K. Manabe. Org. Lett. 7, 4729 (2005). (http://dx.doi.org/10.1021/ol051965w)
25. The angle of O-Bi-O is 165deg, while that of O-Sc-O is 151deg. The torsional angle of two pyridines in the Bi complex is 27.0deg, and that in the Sc complex is 19.4deg. For the Sc complex, see ref. [13].
26. (a). D. J. Ager, I.Prakash, D. R. Schaad. Chem. Rev. 96, 835 (1996); (http://dx.doi.org/10.1021/cr9500038)
26. (b). S. C. Bergmeier. Tetrahedron 56, 2561 (2000); (http://dx.doi.org/10.1016/S0040-4020(00)00149-6)
26. (c). M. Yamashita, K. Yamada, K. Tomioka. Org. Lett. 7, 2369 (2005); (http://dx.doi.org/10.1021/ol050643p)
26. (d). H. C. Kolb, K.B. Sharpless. In Transition Metals for Organic Synthesis, M. Beller, C. Bolm, (Eds.), p. 243, Wiley-VCH, Weinheim (1998).
27. (a). X. L. Hou, J. Wu, L. X. Dai, L. J. Xia, M. H. Tang. Tetrahedron: Asymmetry 9, 1747 (1998); (http://dx.doi.org/10.1016/S0957-4166(98)00153-0)
27. (b). S. Sagawa, H. Abe, Y. Hase, T. Inaba. J. Org. Chem. 64, 4962 (1999); (http://dx.doi.org/10.1021/jo9900883)
27. (c). A. Sekine, T.Ohshima, M. Shibasaki. Tetrahedron 58, 75 (2002); (http://dx.doi.org/10.1016/S0040-4020(01)01088-2)
27. (d). C. Schneider, A. R. Sreekanth, E. Mai. Angew. Chem., Int. Ed. 43, 5691 (2004); (http://dx.doi.org/10.1002/anie.200460786)
27. (e). F. Carree, R. Gil, J. Collin. Org. Lett. 7, 1023 (2005). (http://dx.doi.org/10.1021/ol0475360)
28. K. Manabe, Y. Mori, T. Wakabayashi, W. Nagayama, S. Kobayashi. J. Am. Chem. Soc. 122, 7202 (2000). (http://dx.doi.org/10.1021/ja001420r)
29. (a). S. Otto, J. B. F. N. Engberts. J. Am. Chem. Soc. 121, 6798 (1999); (http://dx.doi.org/10.1021/ja984273u)
29. (b). K. Manabe, S.Kobayashi. Chem. Eur. J. 8, 4094 (2002); (http://dx.doi.org/10.1002/1521-3765(20020916)8:18<4094::AID-CHEM4094>3.0.CO;2-G)
29. (c). D. Sinou, C. Rabeyrin, C. Nguefack. Adv. Synth. Catal. 345, 357 (2003); (http://dx.doi.org/10.1002/adsc.200390040)
29. (d). T. Hamada, K. Manabe, S. Kobayashi. J. Am. Chem. Soc. 126, 7768 (2004). (http://dx.doi.org/10.1021/ja048607t)
30. (a). N. Iranpoor, H. Firouzabadi, M.Shekarize. Org. Biomol. Chem. 1, 724 (2003); (http://dx.doi.org/10.1039/b211697a)
30. (b). R. H. Fan, X. L. Hou. J. Org. Chem. 68, 726 (2003); (http://dx.doi.org/10.1021/jo025983s)
30. (c). T. Ollevier, G. Lavie-Compain. Tetrahedron Lett. 45, 49 (2004). (http://dx.doi.org/10.1016/j.tetlet.2003.10.129)
31. C. Ogawa, S. Azoulay, S. Kobayashi. Heterocycles 66, 201 (2005).
32. (a). S. Kobayashi, H. Ishitani. Chem. Rev. 99, 1069 (1999); (http://dx.doi.org/10.1021/cr980414z)
32. (b). A. E. Taggi, A. M. Hafez, T. Lectka. Acc. Chem. Res. 36, 10 (2003); (http://dx.doi.org/10.1021/ar020137p)
32. (c). S.Kobayashi, M. Ueno. In Comprehensive Asymmetric Catalysis, E. N. Jacobsen, A. Pfaltz, H.Yamamoto (Eds.), Supplement 1, Chap. 29.5, pp. 143-159, Springer, Berlin (2004).
33. S. Kobayashi, K. Manabe, H. Ishitani, J. Matsuo. In Science of Synthesis, Houben-Weyl Methods of Molecular Transformations, Vol. 4, D. Bellus, S. V. Ley, R. Noyori, M. Regitz, E. Schauman, I. Shinkai, E. J. Thomas, B. M. Trost. (Eds.), pp. 317-369, Georg Thieme Verlag, Stuttgart (2002).
34. (a). N. Wolfgang, F. Tanaka, S.-i. Watanabe, N. S. Chowdari, J. M. Turner, R.Thayumanavan, C. F. Barbas III. J. Org. Chem. 68, 9624 (2003); (http://dx.doi.org/10.1021/jo0347359)
34. (b). I. Ibrahem, J. Casas, A.Cordova. Angew. Chem. 116, 6690 (2004); (http://dx.doi.org/10.1002/ange.200460678)
34. (c). I. Ibrahem, J. Casas, A. Cordova. Angew. Chem., Int. Ed. 43, 6528 (2004). (http://dx.doi.org/10.1002/anie.200460678)
35. S. Kobayashi, T. Hamada, K. Manabe. J. Am. Chem. Soc. 124, 5640 (2002). (http://dx.doi.org/10.1021/ja026094p)
36. T. Hamada, K. Manabe, S. Kobayashi, J. Am. Chem. Soc. 126, 7768 (2004). (http://dx.doi.org/10.1021/ja048607t)
37. (a). M. Arend, B. Westermann, N. Risch. Angew. Chem. 110, 1096 (1998); (http://dx.doi.org/10.1002/(SICI)1521-3757(19980420)110:8<1096::AID-ANGE1096>3.0.CO;2-Z)
37. (b). M. Arend, B. Westermann, N. Risch. Angew. Chem., Int. Ed. 37, 1044 (1998). (http://dx.doi.org/10.1002/(SICI)1521-3773(19980504)37:8<1044::AID-ANIE1044>3.0.CO;2-E)
38. Burk reported catalytic asymmetric hydrogenations of N-acylhydrazones: M. J. Burk, J. E. Feaster. J. Am. Chem. Soc. 114, 6266 (1992). (http://dx.doi.org/10.1021/ja00041a067)
39. (a). H. Oyamada, S. Kobayashi. Synlett 249 (1998); (http://dx.doi.org/10.1055/s-1998-1638)
39. (b). S. Kobayashi, K. Sugita, H. Oyamada, Synlett 138 (1999); (http://dx.doi.org/10.1055/s-1999-2566)
39. (c). K. Manabe, H. Oyamada, K. Sugita, S. Kobayashi. J. Org. Chem. 64, 8054 (1999). (http://dx.doi.org/10.1021/jo991009q)
40. S. Kobayashi, Y. Hasegawa, H. Ishitani. Chem. Lett. 1131 (1998). (http://dx.doi.org/10.1246/cl.1998.1131)
41. "Hydrazine and its derivatives", in Kirk-Othmer Encyclopedia of Chemical Technology, 4th ed., Vol. 13, John Wiley, New York (1995).
42. S. Kobayashi, T. Hamada, K. Manabe. Synlett 1140 (2001). (http://dx.doi.org/10.1055/s-2001-15166)

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