寄稿論文 規則性無機ナノ空間が創り出す新しい触媒能 | 東京化成工業

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1 MCM-41 M41 MCM-41 M41 2

2 3 m 2 /g nm nm

3 Mn Ti Ti H N 2 S Ti-MCM-41, H H N H H 2 2 -Urea, CH 2 Cl 2, H 2 S + S 1b 2b 3b 54%, 58% ee Ti M41 H 2 As 4 ZP 4

4 ZP ZS ZS 5

5 Me Me Me Me M41 / 15 mg MeH 1.0 mmol 89% Yield(GC) nm nm Kaliaguine Kevan B-M41 Ni-M41 M41 M41 6

6 R 1 CH or Me R 1 Me SiMe 3 R + M41 CH 2 Cl 2 R 1 M41 Entry Electrophile Enolate MCM-41 / mg/mmol Reaction Conditions Product Yield(%) Me Me Me 1 3 Ph H C, 6 h Ph 84 Me Me Me 2 6 Ph H C, 12 h Ph 64 Me Me Me C, 12 h 90 Me Me C, 3 h Ph Ph Me a 85 b 87 c 90 d entries 1 and 3 entries 2 and 4 a b c d 7

7 M41 Silica gel 60 M41 M41 Al Si/Al = M41 mmol M41 M41 nm 2 H + Me M41 / 90 mg 180 C, 16 h C 5 H 11 Me C 5 H mmol 5.0 ml 85% Yield HZSM-5 M41 M41 M41 M41 8

8 Acid Product Isolated Yield(%) C 2 H 5 H C 2 H 5 Me 33 C 3 H 7 H C 3 H 7 Me 68 C 5 H 11 H 4 C 15 H 31 H C 5 H 11 C 15 H 31 Me Me i C 3 H 7 H i C 3 H 7 Me 68 H Me 76 Ph H Ph Me 66 M4 M41 M41 M C 8 H 17 Cl or 1-C 8 H 17 H M41 / 100 mg 210 C C C 1 2 C 3 C 7 C 6 C 5 C 4 9

9 h µmol g 1 µmol g 1 µmol g 1 µmol g 1 µmol g 1 µmol g 1 M41 mmol g 1 Al µmol g 1 M41 n-c 8 H 17 Cl Ni/Si 2 M41 Ni-M41 Ni-M41 10

10 Ni-M41 ETP Ni-M41 Ni M41 Ni Mo W Re Ni Ni M41 LH 11

11 M41 M41 V 2 5 /aq.h 2 2 M41 cis cis V ion (12 µmol) M41(100 mg) aq. H 2 2 (1 eq.) 1,4-Dioxane (2.0 ml) r.t. 12 h cis-diol trans-diol H H H H p cis cis de cis cis σ cis trans σ de cis M41 M41 H 2 S 4 12

12 CREST 11) 1) A. Corma, Chem. Rev., 97, 2373 (1997); G. Soler-Illia, C. Sanchez, et. al., Chem. Rev., 102, 4093 (2002). 2),, 41, 31 (1999);, 62, 411 (2004);, 27, 628 (2004);, 58, 545 (2005). 3) M. Iwamoto, Y. Tanaka, Catal. Surv. from Jpn., 5, 25 (2001). 4) M. Yonemitsu, Y. Tanaka, M. Iwamoto, J. Catal., 178, 207 (1998). 5) M. Iwamoto, Y. Tanaka, J. Hirosumi, N. Kita, Chem. Lett., 2000, 226; M. Iwamoto, Y. Tanaka, J. Hirosumi, N. Kita, S. Triwahyono, Micro. Meso. Mater., 48, 271 (2001). 6) M. Iwamoto, T. Abe, Y. Tachibana, J. Mol. Catal. A, 155, 143 (2000). 7) P. Wu, M. Iwamoto, Chem. Lett., 27, 1213 (1998); P. Wu, M. Iwamoto, Chem. Mater., in press. 8) M. Iwamoto, H. Kitagawa, Y. Watanabe, Chem. Lett., 31, 814 (2002); H. Takada, Y. Watanabe, M. Iwamoto, Chem. Lett., 33, 62 (2004). 9) Y. Tanaka, N. Sawamura, M. Iwamoto, Tetrahedron Lett., 39, 9457 (1998). 10) M. Iwamoto, Y. Tanaka, N. Sawamura, S. Namba, J. Am. Chem. Soc., 125, (2003). 13

13 12) D. Trong, P. N. Joshi, G. Lemay, S. Kaliaguine, Stud. Sur. Sci. Catal., 97, 543 (1995). 13) M. Hartmann, A. Poppl, L. Kevan, J. Phys. Chem., 100, 9906 (1996). 14) T. Yamamoto, T. Tanaka, T. Funabiki, S. Yoshida, J. Phys. Chem. B, 102, 5830 (1998); A. Ito, T. Kodama, S. Maeda, Y. Masaki, Tetrahedron Lett., 39, 9461 (1998). 15) S. Murata, M. Suzuki, R. Noyori, Tetrahedron, 44, 4259 (1988); T. Sato, J. tera, H. Nozaki, J. Am. Chem. Soc., 112, 901 (1990); J.-X. Chen, K. Sakamoto, A. rita, J. tera, Tetrahedron, 54, 8411 (1998). 16) M. Kawai, M. naka, Y. Izumi, Bull. Chem. Soc. Jpn., 61, 1237 (1988). 17) H. Ishitani, M. Iwamoto, Tetrahedron Lett., 44, 299 (2003). 18) G. A. lah, Friedel-Crafts and Related Reactions, Willey, New York, ),,,, 45, 522 (2003). 20) (a). L. Wang, Y. Ma, X. Ji, H. Yan, Q. Qiu, J. Chem. Soc., Chem. Commun., 1995, (b) J. Kaur, I. V. Kozhevnikov, J. Chem. Soc., Chem. Commum., 2002, (c) M. Hino, K. Arata, J. Chem. Soc., Chem. Commun., 1985, ),,,, 47, 467 (2005). 22) S. H. Sharman, J. Am. Chem. Soc., 84, 2945 (1962); R. M. Roberts, E. K. Baylis, G. J. Fonken, J. Am. Chem. Soc., 85, 3454 (1963). 23),,, pp 31-37, (2001);, 56, 29 (2003); A. M. Al-Jarallah, M. A. B. Siddiqui, A. M. Aitani, A. W. Al-Sa doun, Catal. Today, 14, 1 (1992); T. Cai, Catal. Today, 51, 153 (1999). 24),,, 74, 295 (1953); J. R. Sohn, A. zaki, J. Catal., 59, 303 (1979). 25) P. P. Nill, J. J. Rooney, J. Am. Chem. Soc., 94, 4383 (1972); T. Yamgaguchi, Y. Tanaka, K. Tanabe, J. Catal., 65, 442 (1980). 26) R. H. Grubbs Ed., Handbook of Metathesis, Wiley-VCH Verlag BmbH & Co., Weinheim, ), (2004);, M, D,, 26, 484 (2003). 28),,, A, 3J20 (2005). 29) L. Doan, D. Whalen, J. rg. Chem., 64, 712 (1974). 30) A. Taguchi, T. Abe, M. Iwamoto, Adv. Mater., 10, 667 (1998); Micro. Meso. Mater., 21, 387 (1998). 31) H. kada, N. Nakajima, T. Tanaka, M. Iwamoto, Angew. Chem. Int. Ed., in press. 32),, 28, pp (2005). (Received Jan. 2006) Masakazu Iwamoto Crompton Lanchester Medal 14

4) H. Takayama et al.: J. Med. Chem., 45, 1949 (2002). 5) H. Takayama et al.: J. Am. Chem. Soc., 112, 8635 (2000). 6) H. Takayama et al.: Tetrahedron Lett., 42, 2995 (2001). 9) M. Kitajima et al: Chem.

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