Allylsilanes

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References FOR PERSONAL USE ONLY 920 Science of Synthesis 4.4 Silicon Compounds [1] Sarkar, T. K., Synthesis, (1990), 969. [2] Sarkar, T. K., Synthesis, (1990), 1101. [3] Dow Corning Corp., USA, US 5756796, (1998); Chem. Abstr., (1998) 129, 28070d. [4] Dow Corning Corp., USA, US 5629439, (1997); Chem. Abstr., (1997) 126, 343682s. [5] Dow Corning Corp., USA, US 5616760, (1997); Chem. Abstr., (1997) 126, 264198k. [6] Dow Corning Corp., USA, US 5596120, (1997); Chem. Abstr., (1997) 126, 131635d. [7] Dow Corning Corp., USA, US 5567837, (1996); Chem. Abstr., (1996) 125, 301236y. [8] Dow Corning Corp., USA, US 5567834, (1996); Chem. Abstr., (1996) 125, 301234w. [9] Colvin, E. W., Silicon in Organic Synthesis, Butterworths: London, (1981). [10] Weber, W. P., Silicon Reagents for Organic Synthesis, Springer: New York, (1983). [11] Sakurai, H., Ed., In Organosilicon and Bioorganosilicon Chemistry, Structure, Bonding, Reactivity and Synthetic Applications, Horwood: Chichester, UK, (1985). [12] Colvin, E. W., Silicon Reagents in Organic Synthesis, Academic: London, (1988). [13] Patai, S.; Rappoport, Z., Eds., The Chemistry of Organic Silicon Compounds, Parts 1 and 2, Wiley: Chichester, UK, (1989). [14] Chan, T. H.; Fleming, I., Synthesis, (1979), 761. [15] Sakurai, H., Pure Appl. Chem., (1982) 54,1. [16] Magnus, P. D.; Sarkar, T.; Djuric, S., In Comprehensive Organometallic Chemistry, Wilkinson, G.; Stone, F. G. A.; Abel, E. W., Eds.; Pergamon: New York, (1982); Vol. 7, p 515. [17] Sakurai, H., Pure Appl. Chem., (1985) 57, 1759. [18] Schinzer, D., Synthesis, (1988), 263. [19] Hosomi, A., Acc. Chem. Res., (1988) 21, 200. [20] Majetich, G., In Organic Synthesis, Theory & Applications, Hudlicky, T., Ed.; JAI Press: Greenwich, CT, (1989), p 173. [21] Fleming, I.; Dunogu›s, J.; Smithers, R., Org. React., (1989) 37, 57. [22] Sakurai, H., Synlett, (1989), 1. [23] Fleming, I., In Comprehensive Organic Synthesis, Trost, B. M.; Fleming, I.; Heathcock, C. H., Eds.; Pergamon: Oxford, UK, (1991); Vol. 2, p 563. [24] Chan, T. H.; Wang, D., Chem. Rev., (1992) 92, 995. [25] Yamamoto, Y.; Asao, N., Chem. Rev., (1993) 93, 2207. [26] Chan, T. H.; Wang, D., Chem. Rev., (1995) 95, 1279. [27] Masse, C. E.; Panek, J. S., Chem. Rev., (1995) 95, 1293. [28] Langkopf, E.; Schinzer, D., Chem. Rev., (1995) 95, 1375. [29] Fleming, I.; Barbero, A.; Walter, D., Chem. Rev., (1997) 97, 2063. [30] Luh, T.-Y.; Liu, S.-T., The Chemistry of Organic Silicon Compounds, Rappoport, Z.; Apeloig, Y., Eds.; Wiley: Chichester, UK, (1998); p 1793. [31] Calas, R.; Dunogu›s, J.; Deleris, G.; Piscioti, J., J. Organomet. Chem., (1974) 69, C15. [32] Deleris, G.; Dunogu›s, J.; Calas, R., J. Organomet. Chem., (1975) 93, 43. [33] Fleming, I.; Pearce, A.; Snowden, R. L., J. Chem. Soc., Chem. Commun., (1976), 182. [34] Hosomi, A.; Sakurai, H., Tetrahedron Lett., (1976), 1295. [35] Hosomi, A.; Sakurai, H., J. Am. Chem. Soc., (1977) 99, 1673. [36] Hayashi, T.; Kabeta, K.; Hamachi, I.; Kumada, M., Tetrahedron Lett., (1983) 24, 2865. [37] Hathaway, S. J.; Paquette, L. A., J. Org. Chem., (1983) 48, 3351. [38] Chan, T. H.; Wang, D., Tetrahedron Lett., (1989) 30, 3041. [39] Komatsu, N.; Uda, M.; Suzuki, H.; Takahashi, T.; Domae, T.; Wada, M., Tetrahedron Lett., (1997) 38, 7215. [40] Aggarwal, V. K.; Vennall, G. P., Synthesis, (1988), 1822. [41] Chatgilialoglu, C.; Ferreri, C.; Ballestri, M.; Curran, D. P., Tetrahedron Lett., (1996) 37, 6387. [42] Zhang, L.-C.; Sakurai, H.; Kira, M., Chem. Lett., (1997), 129. [43] Matsumoto, K.; Oshima, K.; Utimoto, K., J. Org. Chem., (1994) 59, 7152. [44] Knölker, H.-J., J. Prakt. Chem., (1997) 339, 304. [45] Knölker, H.-J.; Jones, P. G.; Wanzl, G., Synlett, (1998), 613. [46] Tietze, L. F.; Schimpf, R., Chem. Ber., (1994) 127, 2235. [47] Clive, D. L. J.; Paul, C. C.; Wang, Z., J. Org. Chem., (1997) 62, 7028. [48] Brey, W. S., Silicon-29 Nuclear Magnetic Resonance, In Silicon Compounds, Register and Review, 4th ed., Larson, G. L., Ed.; Petrarch Systems: Bristol, PA, (1987); p 60. Sarkar, T. K., SOS, (2002) 4, 837. 2002 Georg Thieme Verlag KG
FOR PERSONAL USE ONLY References 921 b[49] Sommer, L. H.; Tyler, L. J.; Whitmore, F. C., J. Am. Chem. Soc., (1948) 70, 2872. [50] Mironov, V. F.; Nepomnina, V. V., Izv. Akad. Nauk SSSR, Ser. Khim., (1960), 1419; Chem. Abstr., (1961) 55, 358. [51] Topchiev, A. V.; Nametkin, N. S.; Chernysheva, T. I.; Durgar yan, S. G., Dokl. Akad. Nauk SSSR, (1956) 110, 97; Chem. Abstr., (1957) 51, 4979g; Dokl. Chem. (Engl. Trans.), (1956), 545. [52] Pillot, J.-P.; Dunogu›s, J.; Calas, R., Tetrahedron Lett., (1976), 1871. [53] Slutsky, J.; Kwart, H., J. Am. Chem. Soc., (1973) 95, 8678. [54] Yanagisawa, A.; Habaue, S.; Yamamoto, H., J. Am. Chem. Soc., (1991) 113, 5893. [55] Knölker, H.-J.; Foitzik, N.; Goesmann, H.; Graf, R.; Jones, P. G.; Wanzl, G., Chem. Eur. J., (1997) 3, 538. [56] Reuter, J. M.; Sinha, A.; Salomon, R. G., J. Org. Chem., (1978) 43, 2438. [57] Shimizu, N.; Imazu, S.; Shibata, F.; Tsuno, Y., Bull. Chem. Soc. Jpn., (1991) 64, 1122. [58] Hayashi, T.; Kabeta, K.; Kumada, M., Tetrahedron Lett., (1984) 25, 1499. [59] Sanji, T.; Iwata, M.; Watanabe, M.; Hoshi, T.; Sakurai, H., Organometallics, (1998) 17, 5068. [60] Shono, T.; Matsumura, Y.; Katoh, S.; Kise, N., Chem. Lett., (1985), 463. [61] Yoshida, J.-i.; Muraki, K.; Funahashi, H.; Kawabata, N., J. Org. Chem., (1986) 51, 3996. [62] Rajaonah, M.; Rock, M. H.; BØguØ, J.-P.; Bonnet-Delpon, D.; Condon, S.; NØdØlec, J.-Y., Tetrahedron Lett., (1998) 39, 3137. [63] Torii, S.; Tanaka, H.; Katoh, T.; Morisaki, K., Tetrahedron Lett., (1984) 25, 3207. [64] Wilson, S. R.; Phillips, L. R.; Natalie, K. J., Jr., J. Am. Chem. Soc., (1979) 101, 3340. [65] Andrianome, M.; Delmond, B., Tetrahedron Lett., (1985) 26, 6341. [66] Sarkar, T. K.; Andersen, N. H., Tetrahedron Lett., (1978), 3513. [67] Andersen, N. H.; McCrae, D. A.; Grotjahn, D. B.; Gabhe, S. Y.; Theodore, L. J.; Ippolito, R. M.; Sarkar, T. K., Tetrahedron, (1981) 37, 4069. [68] Trost, B. M.; Chan, D. M. T., J. Am. Chem. Soc., (1983) 105, 2315. [69] Trost, B. M.; Chan, D. M. T.; Nanninga, T. N., Org. Synth., (1984) 62, 58. [70] Ochiai, M.; Fujita, E.; Arimoto, M.; Yamaguchi, H., Chem. Pharm. Bull., (1983) 31, 86. [71] Schlosser, M.; Dahan, R.; Cottens, S., Helv. Chim. Acta, (1984) 67, 284. [72] Desponds, O.; Franzini, L.; Schlosser, M., Synthesis, (1997), 150. [73] Danheiser, R. L.; Takahashi, T.; Bertók, B.; Dixon, B. R., Tetrahedron Lett., (1993) 34, 3845. [74] Schlosser, M.; Desponds, O.; Lehmann, R.; Moret, E.; Rauchschwalbe, G., Tetrahedron, (1993) 49, 10175. [75] Moret, E., Ph.D. Thesis, Universityof Lausanne, (1980). [76] Moret, E.; Franzini, L.; Schlosser, M., Chem. Ber., (1997) 130, 335. [77] Franciotti, M.; Mordini, A.; Taddei, M., Synlett, (1992), 137. [78] Degl Innocenti, A.; Mordini, A.; Pagliai, L.; Ricci, A., Synlett, (1991), 155. [79] Hosomi, A.; Ando, M.; Sakurai, H., Chem. Lett., (1984), 1385. [80] Negishi, E.-i.; Luo, F.-T.; Rand, C. L., Tetrahedron Lett., (1982) 23, 27. [81] Organ, M. G.; Winkle, D. D., J. Org. Chem., (1997) 62, 1881. [82] Itoh, K.; Yogo, T.; Ishii, Y., Chem. Lett., (1977), 103. [83] Hayashi, T.; Konishi, M.; Okamoto, Y.; Kabeta, K.; Kumada, M., J. Org. Chem., (1986) 51, 3772. [84] Organ, M. G.; Murray, A. P., J. Org. Chem., (1997) 62, 1523. [85] Sugihara, Y.; Ogasawara, K., Synlett, (1994), 665. [86] Hayashi, T.; Fujiwa, T.; Okamoto, Y.; Katsuro, Y.; Kumada, M., Synthesis, (1981), 1001. [87] Armstrong, R. J.; Weiler, L., Can. J. Chem., (1983) 61, 214. [88] Polla, M.; Frejd, T., Tetrahedron, (1993) 49, 2701. [89] Saulnier, M. G.; Kadow, J. F.; Tun, M. M.; Langley, D. R.; Vyas, D. M., J. Am. Chem. Soc., (1989) 111, 8320. [90] Loreto, M. A.; Pompei, F.; Tardella, P. A.; Tofani, D., Tetrahedron, (1997) 53, 15853. [91] Hayashi, T.; Katsuro, Y.; Kumada, M., Tetrahedron Lett., (1980) 21, 3915. [92] Gais, H.-J.; Bülow, G., Tetrahedron Lett., (1992) 33, 461. [93] Hevesi, L.; Hermans, B.; Allard, C., Tetrahedron Lett., (1994) 35, 6729. [94] Bhushan, V.; Lohray, B. B.; Enders, D., Tetrahedron Lett., (1993) 34, 5067. [95] Enders, D.; Lohray, B. B., Angew. Chem., (1987) 99, 359; Angew. Chem. Int. Ed. Engl., (1987) 26, 351. [96] Seyferth, D.; Wursthorn, K. R.; Mammarella, R. E., J. Org. Chem., (1977) 42, 3104. [97] Seyferth, D.; Wursthorn, K. R.; Lim, T. F. O.; Sepelak, D. J., J. Organomet. Chem., (1979) 181, 293. [98] Fleming, I.; Paterson, I., Synthesis, (1979), 446. [99] Iio, H.; Ishii, M.; Tsukamoto, M. T.; Tokoroyama, T., Tetrahedron Lett., (1988) 29, 5965. Sarkar, T. K., SOS, (2002) 4, 837. 2002 Georg Thieme Verlag KG
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4.4.40 Product Subclass 40: Allylsi
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matching of both partners is approp
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pressure. Flash chromatography(sili
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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 = +
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Scheme 18 Allylsilanes from Vinyl T
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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
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Scheme 31 Allylsilanes from Allyl A
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mended for the synthesis of Z-allyl
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Allylsilanes 80; General Procedure:
Page 29 and 30:
Scheme 39 Allylsilanes from Allyl C
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Scheme 42 2-Substituted Allylsilane
Page 33 and 34: 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: FOR PERSONAL USE ONLY 4.4.40 Allyls
Page 87 and 88: FOR PERSONAL USE ONLY References 92
Page 89 and 90: FOR PERSONAL USE ONLY References 92
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