Allylsilanes

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FOR PERSONAL USE ONLY 924 Science of Synthesis 4.4 Silicon Compounds b[206] Fleming, I.; Percival, A., J. Chem. Soc., Chem. Commun., (1976), 681. [207] Fleming, I.; Percival, A., J. Chem. Soc., Chem. Commun., (1978), 178. [208] Carter, M. J.; Fleming, I.; Percival, A., J. Chem. Soc., Perkin Trans. 1, (1981), 2415. [209] Koreeda, M.; Ciufolini, M. A., J. Am. Chem. Soc., (1982) 104, 2308. [210] Oppolzer, W.; Burford, S.; Marazza, F., Helv. Chim. Acta, (1980) 63, 555. [211] Burke, S. D.; Strickland, S. M. S.; Powner, T. H., J. Org. Chem., (1983) 48, 454. [212] Sarkar, T. K.; Ghosh, S. K.; Subba Rao, P. S. V.; Satapathi, T. K., Tetrahedron Lett., (1990) 31, 3461. [213] Sarkar, T. K.; Ghosh, S. K.; Subba Rao, P. S. V.; Satapathi, T. K.; Mamdapur, V. R., Tetrahedron, (1992) 48, 6897. [214] Sarkar, T. K.; Ghorai, B. K.; Nandy, S. K.; Mukherjee, B.; Banerji, A., J. Org. Chem., (1997) 62, 6006. [215] Mak, C. C.; Chan, K. S., J. Chem. Soc., Perkin Trans. 1, (1993), 2143. [216] Mak, C. C.; Tse, M. K.; Chan, K. S., J. Org. Chem., (1994) 59, 3585. [217] Landais, Y.; Planchenault, D.; Weber, V., Tetrahedron Lett., (1994) 35, 9549. [218] Bulugahapitiya, P.; Landais, Y.; Parra-Rapado, L.; Planchenault, D.; Weber, V., J. Org. Chem., (1997) 62, 1630. [219] Davies, H. M. L.; Hansen, T.; Rutberg, J.; Bruzinski, P. R., Tetrahedron Lett., (1997) 38, 1741. [220] Hwu, J. R.; Gilbert, B. A.; Lin, L. C.; Liaw, B. R., J. Chem. Soc., Chem. Commun., (1990), 161. [221] Tietze, L. F.; Wünsch, J. R., Synthesis, (1990), 985. [222] Marumoto, S.; Kuwajima, I., J. Am. Chem. Soc., (1993) 115, 9021. [223] Gibson, C.; Buck, T.; Noltemeyer, M.; Brückner, R., Tetrahedron Lett., (1997) 38, 2933. [224] Chatgilialoglu, C.; Ballestri, M.; Vecchi, D.; Curran, D. P., Tetrahedron Lett., (1996) 37, 6383. [225] Chan, T. H.; Labrecque, D., Tetrahedron Lett., (1991) 32, 1149. [226] Soderquist, J.A.; Santiago, B., Tetrahedron Lett., (1989) 30, 5693. [227] Sarkar, T. K.; Ghorai, B. K., J. Chem. Soc., Chem. Commun., (1992), 1184. [228] Sarkar, T. K.; Ghorai, B. K., unpublished results. [229] Ollivier, J.; Salaün, J., Synlett, (1994), 949. [230] Hayashi, T.; Iwamura, H.; Uozumi, Y., Tetrahedron Lett., (1994) 35, 4813. [231] Rajagopalan, S.; Zweifel, G., Synthesis, (1984), 113. [232] Mohr, P., Tetrahedron Lett., (1995) 36, 2453. [233] Tietze, L. F.; Neumann, T.; Kajino, M.; Pretor, M., Synthesis, (1995), 1003. [234] Crowe, W. E.; Goldberg, D. R.; Zhang, Z. J., Tetrahedron Lett., (1996) 37, 2117. [235] Brümmer, O.; Rückert, A.; Blechert, S., Chem. Eur. J., (1997) 3, 441. [236] Schneider, M. F.; Lucas, N.; Velder, J.; Blechert, S., Angew. Chem., (1997) 109, 257; Angew. Chem. Int. Ed. Engl., (1997) 36, 257. [237] Schuster, M.; Lucas, N.; Blechert, S., Chem. Commun. (Cambridge), (1997), 823. [238] Fujiwara, T.; Takamori, M.; Takeda, T., Chem. Commun. (Cambridge), (1998), 51. [239] Olofsson, K.; Larhed, M.; Hallberg, A., J. Org. Chem., (1998) 63, 5076. [240] Bardot, V.; Remuson, R.; Gelas-Mialhe, Y.; Gramain, J.-C., Synlett, (1996), 37. [241] Araki, S.; Ito, H.; Butsugan, Y., J. Org. Chem., (1988) 53, 1831. [242] Krief, A.; Dumont, W.; Markó, I. E.; Murphy, F.; Vanherck, J.-C.; Duval, R.; Ollevier, T.; Abel, U., Synlett, (1998), 1219. [243] Ryter, K.; Livinghouse, T., J. Org. Chem., (1997) 62, 4842. [244] Ramon, D. J.; Yus, M., Tetrahedron, (1993) 49, 10103. [245] Minato, A.; Suzuki, K.; Tamao, K.; Kumada, M., Tetrahedron Lett., (1984) 25, 83. [246] Hosomi, A.; Sakata, Y.; Sakurai, H., Tetrahedron Lett., (1985) 26, 5175. [247] Hosomi, A.; Otaka, K.; Sakurai, H., Tetrahedron Lett., (1986) 27, 2881. [248] Kang, K.-T.; U, J. S.; Park, D. K.; Kim, J. K.; Kim, W. J., Bull. Korean Chem. Soc., (1995) 16, 464. [249] Majetich, G.; Nishidie, H.; Zhang, Y., J. Chem. Soc., Perkin Trans. 1, (1995), 453. [250] Kang, K.-T.; Sung, T. M.; Kim, J. K.; Kwon, Y. M., Synth. Commun., (1997) 27, 1173. [251] Mordini, A.; Palio, G.; Ricci, A.; Taddei, M., Tetrahedron Lett., (1988) 29, 4991. [252] Soderquist, J. A.; Santiago, B.; Rivera, I., Tetrahedron Lett., (1990) 31, 4981. [253] Ni, Z.-J.; Luh, T.-Y., J. Chem. Soc., Chem. Commun., (1988), 1011. [254] Fugami, K.; Oshima, K.; Utimoto, K.; Nozaki, H., Tetrahedron Lett., (1986) 27, 2161. [255] Fugami, K.; Hibino, J. -I.; Nakatsukasa, S.; Matsubara, S.; Oshima, K.; Utimoto, K.; Nozaki, H., Tetrahedron, (1988) 44, 4277. [256] Pornet, J.; Khouz, B.; Miginiac, L., Tetrahedron Lett., (1985) 26, 1861. [257] Pornet, J.; Rayadh, A.; Miginiac, L., Tetrahedron Lett., (1986) 27, 5479. [258] Sarkar, T. K.; Ghosh, S. K., Tetrahedron Lett., (1987) 28, 2061. Sarkar, T. K., SOS, (2002) 4, 837. 2002 Georg Thieme Verlag KG
FOR PERSONAL USE ONLY References 925 b[259] Sarkar, T. K.; Ghosh, S. K.; Satapathi, T. K., Tetrahedron, (1990) 46, 1885. [260] Barluenga, J.; Fernµndez-Simón, J. L.; Concellón, J. M.; Yus, M., Tetrahedron Lett., (1989) 30, 5927. [261] Ochiai, M.; Sumi, K.; Fujita, E.; Tada, S.-i., Chem. Pharm. Bull., (1983) 31, 3346. [262] Hori, Y.; Mitsudo, T.-a.; Watanabe, Y., Bull. Chem. Soc. Jpn., (1988) 61, 3011. [263] Terao, J.; Torii, K.; Saito, K.; Kambe, N.; Baba, A.; Sonoda, N., Angew. Chem., (1998) 110, 2798; Angew. Chem. Int. Ed., (1998) 37, 2653. [264] Pillot, J.-P.; DØlØris, G.; Dunogu›s, J.; Calas, R., J. Org. Chem., (1979) 44, 3397. [265] Saito, S.; Shimada, K.; Yamamoto, H.; Martinez de Marigorta, E.; Fleming, I., Chem. Commun. (Cambridge), (1997), 1299. [266] Tanigawa, Y.; Fuse, Y.; Murahashi, S.-I., Tetrahedron Lett., (1982) 23, 557. [267] Shiragami, H.; Kawamoto, T.; Utimoto, K.; Nozaki, H., Tetrahedron Lett., (1986) 27, 589. [268] Shiragami, H.; Kawamoto, T.; Imi, K.; Matsubara, S.; Utimoto, K.; Nozaki, H., Tetrahedron, (1988) 44, 4009. [269] Wang, K. K.; Yang, K. E., Tetrahedron Lett., (1987) 28, 1003. [270] Wang, K. K.; Dhumrongvaraporn, S., Tetrahedron Lett., (1987) 28, 1007. [271] Fleming, I.; Au-Yeung, B.-W., Tetrahedron, (1981) 37 (Suppl. 9), 13. [272] Fujii, K.; Hara, O.; Sakagami, Y., Biosci. Biotech. Biochem., (1997) 61, 1394. [273] Matsuda, I.; Kato, T.; Sato, S.; Izumi, Y., Tetrahedron Lett., (1986) 27, 5747. [274] Tzeng, D.; Weber, W. P., J. Org. Chem., (1981) 46, 693. [275] Wang, D.; Chan, T.-H., J. Chem. Soc., Chem. Commun., (1984), 1273. [276] Trost, B. M.; Yoshida, J.-i.; Lautens, M., J. Am. Chem. Soc., (1983) 105, 4494. [277] Molander, G. A.; Shubert, D. C., Tetrahedron Lett., (1986) 27, 787. [278] Wilson, S. R.; Zucker, P. A., J. Org. Chem., (1988) 53, 4682. [279] Salomon, R. G.; Coughlin, D. J., J. Org. Chem., (1979) 44, 3784. [280] Cozzi, P. G.; Tagliavini, E.; Umani-Ronchi, A., Gazz. Chim. Ital., (1997) 127, 247. [281] Denmark, S. E.; Coe, D. M.; Pratt, N. E.; Griedel, B. D., J. Org. Chem., (1994) 59, 6161. [282] Nakajima, M.; Saito, M.; Shiro, M.; Hashimoto, S.-i., J. Am. Chem. Soc., (1998) 120, 6419. [283] Pellissier, H.; Toupet, L.; Santelli, M., J. Org. Chem., (1994) 59, 1709. [284] Brain, C. T.; Thomas, E. J., Tetrahedron Lett., (1997) 38, 2387. [285] Organ, M. G.; Winkle, D. D.; Huffmann, J., J. Org. Chem., (1997) 62, 5254. [286] Lee, T. V.; Boucher, R. J.; Rockell, C. J. M., Tetrahedron Lett., (1988) 29, 689. [287] Kobayashi, S.; Nishio, K., J. Org. Chem., (1994) 59, 6620. [288] Wang, Z.; Kisanga, P.; Verkade, J. G., J. Org. Chem., (1999) 64, 6459. [289] Suginome, M.; Iwanami, T.; Ito, Y., J. Org. Chem., (1998) 63, 6096. [290] Franciotti, M.; Mann, A.; Mordini, A.; Taddei, M., Tetrahedron Lett., (1993) 34, 1355. [291] Hayashi, T.; Okamoto, Y.; Kabeta, K.; Hagihara, T.; Kumada, M., J. Org. Chem., (1984) 49, 4224. [292] Sarkar, T. K.; Gangopadhyay, P.; Ghorai, B. K.; Nandy, S. K.; Fang, J.-M., Tetrahedron Lett., (1998) 39, 8365. [293] Soderquist, J. A.; Rane, A. M.; Lopez, C. J., Tetrahedron Lett., (1993) 34, 1893. [294] Tokoroyama, T.; Pan, L.-R., Tetrahedron Lett., (1989) 30, 197. [295] Corey, E. J.; Burk, R. M., Tetrahedron Lett., (1987) 28, 6413. [296] Snider, B. B.; Lu, Q., J. Org. Chem., (1994) 59, 8065. [297] Tietze, L. F.; Schünke, C., Angew. Chem., (1995) 107, 1901; Angew. Chem. Int. Ed. Engl., (1995) 34, 1731. [298] Trost, B. M.; Chan, D. M. T., J. Am. Chem. Soc., (1979) 101, 6429. [299] Cleary, D. G.; Paquette, L. A., Synth. Commun., (1987) 17, 497. [300] Trost, B. M.; Mac Pherson, D. T., J. Am. Chem. Soc., (1987) 109, 3483. [301] Molander, G. A.; Shubert, D. C., J. Am. Chem. Soc., (1987) 109, 6877. [302] Trost, B. M.; Seoane, P. R., J. Am. Chem. Soc., (1987) 109, 615. [303] Hoffmann, H. M. R., personal communication. [304] Akiyama, T.; Ishikawa, K.; Ozaki, S., Chem. Lett., (1994), 627. [305] Akiyama, T.; Yasusa, T.; Ishikawa, K.; Ozaki, S., Tetrahedron Lett., (1994) 35, 8401. [306] Panek, J. S.; Beresis, R., J. Org. Chem., (1993) 58, 809. [307] Schinzer, D.; Panke, J. G., J. Org. Chem., (1996) 61, 4496. [308] Akiyama, T., personal communication. [309] Kang, K.-T.; Kim, S. S.; Lee, J. C.; U, J. S., Tetrahedron Lett., (1992) 33, 3495. [310] Kang, K.-T., personal communication. [311] Blechert, S., personal communication. Sarkar, T. K., SOS, (2002) 4, 837. 2002 Georg Thieme Verlag KG
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4.4.40 Product Subclass 40: Allylsi
Page 3 and 4:
matching of both partners is approp
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pressure. Flash chromatography(sili
Page 7 and 8:
Scheme 11 From Allylic Halides by E
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similar protocol starting with but-
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+ PhMe2Si MgCl Cl Br (R,S)-PPFA = +
Page 13 and 14:
Scheme 18 Allylsilanes from Vinyl T
Page 15 and 16:
Trimethyl(non-2-enyl)silane (44); T
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complex which reacts with the carbo
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(2-Cyclohexylidenepropyl)trimethyls
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(2 ” 10 3 kPa)±depressurization
Page 23 and 24:
Scheme 31 Allylsilanes from Allyl A
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mended for the synthesis of Z-allyl
Page 27 and 28:
Allylsilanes 80; General Procedure:
Page 29 and 30:
Scheme 39 Allylsilanes from Allyl C
Page 31 and 32:
Scheme 42 2-Substituted Allylsilane
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FOR PERSONAL USE ONLY 4.4.40 Allyls
Page 35 and 36:
Conversion of â-Hydroxy Acids 99 i
Page 37 and 38: Scheme 48 Allylsilanes by Carbocupr
Page 39 and 40: 119. [183,185] The trick for succes
Page 41 and 42: the mixture was washed with sat. aq
Page 43 and 44: (+)-(3R,4E)-N,N-Dimethyl-3-(trimeth
Page 45 and 46: Scheme 57 From Alkenyl Fischer Carb
Page 47 and 48: 4.4.40.37 Method 37: From Allyl Sul
Page 49 and 50: Allyltris(trimethylsilyl)silane (15
Page 51 and 52: the Z-isomer; very little, if any,
Page 53 and 54: Pd2(dba)3 CHCl3 (cat.) (R)-MOP-phen
Page 55 and 56: Scheme 70 An Alk-2-enylsilane by Ca
Page 57 and 58: (E)-Trimethyl[3-(4-tolyl)allyl]sila
Page 59 and 60: FOR PERSONAL USE ONLY 4.4.40 Allyls
Page 61 and 62: Scheme 77 2-Substituted Allylsilane
Page 63 and 64: stream of argon, which was passed t
Page 65 and 66: Z-Vinylsilanes carrying a (tributyl
Page 67 and 68: 1-tert-Butyl-1-vinylcyclohexane (21
Page 69 and 70: 4.4.40.59 Method 59: Allylation of
Page 71 and 72: (5SR,6SR,9RS,10RS)-6,9-Divinyltetra
Page 73 and 74: Scheme 97 Synthesis of Homoallylic
Page 75 and 76: Scheme 102 Synthesis of Enantiomeri
Page 77 and 78: Scheme 106 Diastereoselective Synth
Page 79 and 80: stirred for 18 h at ±78 8C, and 5
Page 81 and 82: shaken with some solid K 2CO 3 and
Page 83 and 84: FOR PERSONAL USE ONLY 4.4.40 Allyls
Page 85 and 86: FOR PERSONAL USE ONLY References 92
Page 87: FOR PERSONAL USE ONLY References 92
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