Pure and Applied Chemistry

Pure Appl. Chem., 2008, Vol. 80, No. 4, pp. 763-776

http://dx.doi.org/10.1351/pac200880040763

Synthesis of optically active heterocyclic compounds using Pd-catalyzed asymmetric reactions as a key step

References

• 1. (a). M. Sodeoka, K. Ohrai, M. Shibasaki. J. Org. Chem. 60, 2648 (1995); (http://dx.doi.org/10.1021/jo00114a002)
• 1. (b). M. Sodeoka, R.Tokunoh, F. Miyazaki, E. Hagiwara, M. Shibasaki. Synlett 463 (1997);
• 1. (c). M. Sodeoka, M.Shibasaki. Pure Appl. Chem. 70, 411 (1998). (http://dx.doi.org/10.1351/pac199870020411)
• 2. (a). E. Hagiwara, A. Fujii, M. Sodeoka. J. Am. Chem. Soc. 120, 2474 (1998); (http://dx.doi.org/10.1021/ja973962n)
• 2. (b). A. Fujii, E.Hagiwara, M. Sodeoka. J. Am. Chem. Soc. 121, 5450 (1999); (http://dx.doi.org/10.1021/ja9902827)
• 2. (c). A. Fujii, E. Hagiwara, M.Sodeoka. J. Synth. Org. Chem. Jpn. 58, 728 (2000).
• 3. (a). Y. Hamashima, D. Hotta, M. Sodeoka. J. Am. Chem. Soc. 124, 11240 (2002); (http://dx.doi.org/10.1021/ja027075i)
• 3. (b). Y.Hamashima, D. Hotta, N. Umebayashi, Y. Tsuchiya, T. Suzuki, M. Sodeoka. Adv. Synth. Catal. 347, 1576 (2005). (http://dx.doi.org/10.1002/adsc.200505199)
• 4. Y. Hamashima, N. Sasamoto, D. Hotta, H. Somei, N. Umebayashi, M. Sodeoka. Angew. Chem., Int. Ed. 44, 1525 (2005). (http://dx.doi.org/10.1002/anie.200462202)
• 5. I. Fukuchi, Y. Hamashima, M. Sodeoka. Adv. Synth. Catal. 349, 509 (2007). (http://dx.doi.org/10.1002/adsc.200600568)
• 6. (a). Y. Hamashima, K. Yagi, H. Takano, L. Tamas, M. Sodeoka. J. Am. Chem. Soc. 124, 14530 (2002); (http://dx.doi.org/10.1021/ja028464f)
• 6. (b). Y. Hamashima, H. Takano, D. Hotta, M. Sodeoka. Org. Lett. 5, 3225 (2003); (http://dx.doi.org/10.1021/ol035053a)
• 6. (c). Y.Hamashima, T. Suzuki, Y. Shimura, T. Shimizu, N. Umebayashi, T. Tamura, N. Sasamoto, M.Sodeoka. Tetrahedron Lett. 46, 1447 (2005); (http://dx.doi.org/10.1016/j.tetlet.2005.01.018)
• 6. (d). Y. Hamashima, T. Suzuki, H. Takano, Y.Shimura, Y. Tsuchiya, K. Moriya, T. Goto, M. Sodeoka. Tetrahedron 62, 7168 (2006); (http://dx.doi.org/10.1016/j.tet.2005.12.070)
• 6. (e). Y.Hamashima, M. Sodeoka. Synlett 1467 (2006);
• 6. (f). K. Moriya, Y. Hamashima, M. Sodeoka. Synlett 1139 (2007);
• 6. (g). T. Suzuki, Y. Hamashima, M.Sodeoka. Angew. Chem., Int. Ed. 46, 5435 (2007). (http://dx.doi.org/10.1002/anie.200701071)
• 7. (a). M. Sodeoka, Y. Hamashima. Bull. Chem. Soc. Jpn. 78, 941 (2005); (http://dx.doi.org/10.1246/bcsj.78.941)
• 7. (b). M.Sodeoka, Y. Hamashima. Pure Appl. Chem. 78, 477 (2006). (http://dx.doi.org/10.1351/pac200678020477)
• 8. M. Chrzanowska, M. D. Rozwadowska. Chem. Rev. 104, 3341 (2004). (http://dx.doi.org/10.1021/cr030692k)
• 9. (a). N. Uematsu, A. Fujii, S. Hashiguchi, T. Ikariya, R. Noyori. J. Am. Chem. Soc. 118, 4916 (1996); (http://dx.doi.org/10.1021/ja960364k)
• 9. (b). M. S. Taylor, E. N. Jacobsen. J. Am. Chem. Soc. 126, 10558 (2004); (http://dx.doi.org/10.1021/ja046259p)
• 9. (c). J. Seayad, A. M. Seayad, B. List. J. Am. Chem. Soc. 128, 1086 (2006); (http://dx.doi.org/10.1021/ja057444l)
• 9. (d). K. Funabashi, H. Ratni, M. Kanai, M. Shibasaki. J. Am. Chem. Soc. 123, 10784 (2001); (http://dx.doi.org/10.1021/ja016935c)
• 9. (e). T. Itoh, M. Miyazaki, H. Fukuoka, K. Nagata, A.Ohsawa. Org. Lett. 8, 1295 (2006); (http://dx.doi.org/10.1021/ol0530326)
• 9. (f). Z. Li, P. D. MacLeod, C.-J. Li. Tetrahedron: Asymmetry 17, 590 (2006); (http://dx.doi.org/10.1016/j.tetasy.2006.02.007)
• 9. (g). A. M. Taylor, S. L. Schreiber. Org. Lett. 8, 143 (2006); (http://dx.doi.org/10.1021/ol0526165)
• 9. (h). Y. Ukaji, Y. Shimizu, Y. Kenmoku, A. Ahmed, K. Inomata. Chem. Lett. 59 (1997). (http://dx.doi.org/10.1246/cl.1997.59)
• 10. (a). S.-I. Murahashi, Y. Imada, T. Kawakami, K. Harada, Y. Yonemushi, N. Tomita. J. Am. Chem. Soc. 124, 2888 (2002); (http://dx.doi.org/10.1021/ja0176649)
• 10. (b). T. Itoh, M. Yokoya, K. Miyauchi, K. Nagata, A. Ohsawa. Org. Lett. 5, 4301 (2003); (http://dx.doi.org/10.1021/ol030103x)
• 10. (c). M. S. Taylor, N. Tokunaga, E. N. Jacobsen. Angew. Chem., Int. Ed. 44, 6700 (2005); (http://dx.doi.org/10.1002/anie.200502277)
• 10. (d). K. Frisch, A. Landa, S. Saaby, K. A. Jorgensen. Angew. Chem., Int. Ed. 44, 6058 (2005). (http://dx.doi.org/10.1002/anie.200501900)
• 11. N. Sasamoto, C. Dubs, Y. Hamashima, M. Sodeoka. J. Am. Chem. Soc. 128, 14010 (2006). (http://dx.doi.org/10.1021/ja065646r)
• 12. P. Kirsch. Modern Fluoroorganic Chemistry: Synthesis, Reactivity, Applications, Wiley-VCH, Weinheim (2004).
• 13. V. A. Soloshonok. Enantiocontrolled Synthesis of Fluoro-Organic Compounds: Stereochemical Challenge and Biomedicinal Targets, John Wiley, New York (1999).
• 14. (a). H. Ibrahim, A. Togni. Chem. Commun. 1147 (2004); (http://dx.doi.org/10.1039/b317004g)
• 14. (b). J.-A. Ma, D. Cahard. Chem. Rev. 104, 6119 (2004). (http://dx.doi.org/10.1021/cr030143e)
• 15. T. Suzuki, T. Goto, Y. Hamashima, M. Sodeoka. J. Org. Chem. 72, 246 (2007). (http://dx.doi.org/10.1021/jo062048m)
• 16. Y. Hamashima, T. Suzuki, H. Takano, Y. Shimura, M. Sodeoka. J. Am. Chem. Soc. 127, 10164 (2005). (http://dx.doi.org/10.1021/ja0513077)
• 17. Unpublished data.
• 18. P. Hewawasam, V. K. Gribkoff, Y. Pendri, S. I. Dworetzky, N. A. Meanwell, E. Martinez, C. G. Boissard, D. J. Post-Munson, J. T. Trojnacki, K. Yeleswaram, L. M. Pajor, J. Knipe, Q. Gao, R.Perrone, J. E. Starrett Jr. Bioorg. Med. Chem. Lett. 12, 1023 (2002) and refs. therein.
• 19. Y. Hamashima, H. Somei, Y. Shimura, T. Tamura, M. Sodeoka. Org. Lett. 6, 1861 (2004). (http://dx.doi.org/10.1021/ol0493711)
• 20. Y. Hamashima. Chem. Pharm. Bull. 54, 1351 (2006). (http://dx.doi.org/10.1248/cpb.54.1351)
• 21. (a). E. Juaristi. Enantioselective Synthesis of b-Amino Acids, John Wiley, New York (1997);
• 21. (b). M. Liu, M. P. Sibi. Tetrahedron 58, 7991 (2002). (http://dx.doi.org/10.1016/S0040-4020(02)00991-2)
• 22. M. E. Brousseau, E. J. Schaefer, M. L. Wolfe, L. T. Bloedon, A. G. Digenio, R. W. Clark, J. P. Mancuso, D. J. Rader. New Engl. J. Med. 350, 1505 (2004). (http://dx.doi.org/10.1056/NEJMoa031766)
• 23. M. Guino, P. H. Phua, J.-C. Caille, K. K. Hii. J. Org. Chem. 72, 6290 (2007). (http://dx.doi.org/10.1021/jo071031g)
• 24. Y. Tsuchiya, Y. Hamashima, M. Sodeoka. Org. Lett. 8, 4851 (2006). (http://dx.doi.org/10.1021/ol0619157)
• 25. (a). Y. Moritani, D. H. Appella, V. Jurkauskas, S. L. Buchwald. J. Am. Chem. Soc. 122, 6797 (2000); (http://dx.doi.org/10.1021/ja0009525)
• 25. (b). B. H. Lipshutz, J. M. Servesko. Angew. Chem., Int. Ed. 42, 4789 (2003); (http://dx.doi.org/10.1002/anie.200352313)
• 25. (c). Y. Kanazawa, Y. Tsuchiya, K. Kobayashi, T. Shiomi, J. Itoh, M. Kikuchi, Y.Yamamoto, H. Nishiyama. Chem.Eur. J. 12, 63 (2006); (http://dx.doi.org/10.1002/chem.200500841)
• 25. (d). S. G. Ouellet, J. B. Tuttle, D. W. C. MacMillan. J. Am. Chem. Soc. 127, 32 (2005). (http://dx.doi.org/10.1021/ja043834g)
• 26. (a). J. A. Mueller, C. P. Goller, M. S. Sigman. J. Am. Chem. Soc. 126, 9724 (2004); (http://dx.doi.org/10.1021/ja047794s)
• 26. (b). M. M. Konnick, B. A. Gandhi, I.A. Guzei, S. S. Stahl. Angew. Chem., Int. Ed. 45, 2904 (2006). (http://dx.doi.org/10.1002/anie.200600532)
• 27. (a). A. Robinson, H.-Y. Li, J.Feaster. Tetrahedron Lett. 37, 8321 (1996); (http://dx.doi.org/10.1016/0040-4039(96)01796-0)
• 27. (b). G. Cravotto, G. M. Nano, G. Palmisano, S.Tagliapietra. Tetrahedron: Asymmetry 12, 707 (2001); (http://dx.doi.org/10.1016/S0957-4166(01)00124-0)
• 27. (c). N. Halland, T. Hansen, K. A. Jorgensen. Angew. Chem., Int. Ed. 42, 4955 (2003). (http://dx.doi.org/10.1002/anie.200352136)