Silyl Ethers - Thieme Chemistry
Silyl Ethers - Thieme Chemistry Silyl Ethers - Thieme Chemistry
tert-Butoxydiphenylsilyl ethers possess stability towards acidic hydrolysis that is comparable to that of tert-butylmethoxyphenylsilyl ethers. [109] Like the latter group, they are also quite labile towards fluoride. An advantage of the tert-butoxydiphenylsilyl group over the tert-butylmethoxyphenylsilyl residue is that it is achiral and, hence, does not produce diastereomeric silyl ethers. References FOR PERSONAL USE ONLY 410 Science of Synthesis 4.4 Silicon Compounds [1] Greene, T. W.; Wuts, P. G. M., In Protective Groups in Organic Synthesis, 3rd ed., Wiley-Interscience: New York, (1999); pp 113±148. [2] Kocien ski, P. J., In Protecting Groups, Thieme: Stuttgart, (1994); pp 28±42. [3] van Look, G.; Simchen, G.; Heberle, J., Silylating Agents, Fluka Chemie AG: Buchs, Switzerland, (1995). [4] Nelson, T. D.; Crouch, R. D., Synthesis, (1996), 1031. [5] Chen, X.; Hortelano, E. R.; Eliel, E. L.; Frye, S. V., J. Am. Chem. Soc., (1992) 114, 1778. [6] West, R.; Wilson, L. S.; Powell, D. L., J. Organomet. Chem., (1979) 178,5. [7] Keck, G. E.; Castellino, S., Tetrahedron Lett., (1987) 28, 281. [8] Evans, D. A.; Halstead, D. P.; Allison, B. D., Tetrahedron Lett., (1999) 40, 4461. [9] Wuts, P. G. M.; Bigelow, S. S., J. Org. Chem., (1988) 53, 5023. [10] Mulzer, J.; Schöllhorn, B., Angew. Chem. Int. Ed. Engl., (1990) 29, 431. [11] Peters, U.; Bankova, W.; Welzel, P., Tetrahedron, (1987) 43, 3803. [12] Crich, D.; Ritchie, T. J., Carbohydr. Res., (1990) 197, 324. [13] Beaucage, S. L.; Iyer, R. P., Tetrahedron, (1992) 48, 2223. [14] Colvin, E., In Silicon in Organic Synthesis, Butterworth: Boston, (1981); pp 30±39. [15] Brook, A. G., J. Am. Chem. Soc., (1958) 80, 1886. [16] Eisch, J. J.; Tasi, M.-R., J. Organomet. Chem., (1982) 225,5. [17] Brook, A. G.; Pascol, J. D., J. Am. Chem. Soc., (1971) 93, 6224. [18] Matsuda, I.; Murata, S.; Ishii, Y., J. Chem. Soc., Perkin Trans. 1, (1979), 26. [19] Gornowicz, G. A.; West, R., J. Organomet. Chem., (1971) 28, 25. [20] West, R.; Lowe, R.; Stewart, H. F.; Wright, A., J. Am. Chem. Soc., (1971) 93, 282. [21] Simchen, G.; Pfletschinger, J., Angew. Chem. Int. Ed. Engl., (1976) 15, 428. [22] Birkofer, L.; Ritter, A.; Bentz, F., Chem. Ber., (1964) 97, 2196. [23] Sabes, S. F.; Urbanek, R. A.; Forsyth, C. J., J. Am. Chem. Soc., (1998) 120, 2534. [24] Emde, H.; Domsch, D.; Feger, H.; Frick, U.; Götz, A.; Hergott, H. H.; Hofmann, K.; Kober, W.; Krägeloh, K.; Oesterle, T.; Steppan, W.; West, W.; Simchen, G., Synthesis, (1982), 1. [25] Murai, A., Tetrahedron, (1998) 54, 21. [26] Mai, K.; Patil, G., J. Org. Chem., (1986) 51, 3545. [27] Churcher, I.; Hallett, D.; Magnus, P., J. Am. Chem. Soc., (1998) 120, 10350. [28] Galbraith, M. N.; Horn, D. H. S.; Middleton, E. J.; Hackney, R. J., J. Chem. Soc., Chem. Commun., (1968), 466. [29] Horning, M. G.; Boucher, E. A.; Moss, A. M., J. Gas Chromatogr., (1967) 5, 297. [30] Coleman, R. S.; Kong, J.-S., J. Am. Chem. Soc., (1998) 120, 3538. [31] Nicolaou, K. C.; Xu, J. Y.; Kim, S.; Pfefferkorn, J.; Ohshima, T.; Vourloumis, D.; Hosokawa, S., J. Am. Chem. Soc., (1998) 120, 8661. [32] Krohn, K.; Micheel, J., Tetrahedron, (1998) 54, 4827. [33] Oka, T.; Fujiwara, K.; Murai, A., Tetrahedron, (1998) 54, 21. [34] Wender, P. A.; Jesudason, C. D.; Nakahira, H.; Tamura, N.; Tebbe, A. L.; Ueno, Y., J. Am. Chem. Soc., (1997) 119, 12976. [35] Hart, T. W.; Metcalfe, D. A.; Scheinmann, F., J. Chem. Soc., Chem. Commun., (1979), 156. [36] Roush, W. R.; Russo-Rodriguez, S., J. Org. Chem., (1987) 52, 598. [37] Shimizu, S.; Nakamura, S.; Nakada, M.; Shibasaki, M., Tetrahedron, (1996) 52, 13363. [38] Stoermer, D.; Caron, S.; Heathcock, C., J. Org. Chem., (1996) 61, 9115. [39] Evans, D. A.; Ratz, A. M.; Huff, B. E.; Sheppard, G. S., J. Am. Chem. Soc., (1995) 117, 3448. [40] Heathcock, C. H.; Young, S. D.; Hagen, J. P.; Pilli, R.; Badertscher, U., J. Org. Chem., (1985) 50, 2095. [41] Evans, D. A.; Kim, A. S.; Metternich, R.; Novack, V. J., J. Am. Chem. Soc., (1998) 120, 5921. [42] Peishoff, C. E.; Jorgensen, W., J. Org. Chem., (1983) 48, 1970. White, J. D.; Carter, R. G., SOS, (2002) 4, 371. 2002 Georg Thieme Verlag KG
FOR PERSONAL USE ONLY References 411 b[43] Marshall, J. A.; Johns, B., J. Org. Chem., (1998) 63, 7885. [44] Magnus, P.; Miknis, G. F.; Press, N. J.; Grandjean, D.; Taylor, G. M.; Harling, J., J. Am. Chem. Soc., (1997) 119, 6739. [45] Clink, R. D.; Forsyth, C. J., J. Org. Chem., (1997) 62, 5672. [46] Corey, E. J.; Venkateswarlu, A., J. Am. Chem. Soc., (1972) 94, 6190. [47] Trost, B. M.; Li, Y., J. Am. Chem. Soc., (1996) 118, 6625. [48] Chaudhary, S. K.; Hernandez, O., Tetrahedron Lett., (1979), 99. [49] Lu, Y.-F.; Fallis, A. G., Can. J. Chem., (1995) 73, 2239. [50] Thomas, E. J.; Williams, A. C., J. Chem. Soc., Perkin Trans. 1, (1995), 351. [51] Corey, E. J.; Cho, H.; Rücher, C.; Hua, D. H., Tetrahedron Lett., (1981) 22, 3455. [52] Krafft, M. E.; Dasse, O. A.; Fu, Z., J. Org. Chem., (1999) 64, 2475. [53] Saito, T.; Suzuki, T.; Morimoto, M.; Akiyama, C.; Ochiai, T.; Takeuchi, K.; Matsumoto, T.; Suzuki, K., J. Am. Chem. Soc., (1998) 120, 11633. [54] Ye, B.; Nakamura, H.; Murai, A., Tetrahedron, (1996) 52, 6361. [55] Yamazaki, T.; Oniki, T.; Kitazume, T., Tetrahedron, (1996) 52, 11753. [56] Ulibarri, G.; Nadler, W.; Skrydstrup, T.; Audrain, H.; Chiaroni, A.; Riche, C.; Grierson, D. S., J. Org. Chem., (1995) 60, 2753. [57] Ireland, R. E.; Gleason, J. L.; Gegnas, L. D.; Highsmith, T. K., J. Org. Chem., (1996) 61, 6856. [58] Nicolaou, K. C.; Ninkovic, S.; Sarabia, F.; Vourloumis, D.; He, Y.; Vallberg, H.; Finlay, M. R. V.; Yang, Z., J. Am. Chem. Soc., (1997) 119, 7974. [59] Middleton, W. J., US 3 940 402, (1976); Chem. Abstr., (1976) 85, P6388j. [60] Noyori, R.; Nishida, I.; Sakata, J.; Nishizawa, M., J. Am. Chem. Soc., (1980) 102, 1223. [61] Holton, R. A.; Kim, H.-B.; Somoza, C.; Liang, F.; Biediger, R. J.; Boatman, P. D.; Shindo, M.; Smith, C. C.; Kim, S.; Nadizadeh, H.; Suzuki, Y.; Tao, C.; Vu, P.; Tang, S.; Zhang, P.; Murthi, K. K.; Gentile, L. N.; Liu, J. H., J. Am. Chem. Soc., (1994) 116, 1599. [62] Nicolaou, K. C.; Webber, S. E., Synthesis, (1986), 453. [63] Ireland, R. E.; Varney, M. D., J. Org. Chem., (1986) 51, 635. [64] Davies, J. S.; Higginbotham, C. L.; Tremeer, E. J.; Brown, C., J. Chem. Soc., Perkin Trans. 1, (1992), 3043. [65] Crimmins, M. T.; Al-awar, R. S.; Vallin, I. M.; Hollis, W. G., Jr.; O Mahony, R.; Lever, J. G.; Bankaitis-Davis, D. M., J. Am. Chem. Soc., (1996) 118, 7513. [66] Kende, A. S.; Liu, K.; Kaldor, I.; Dorey, G.; Koch, K., J. Am. Chem. Soc., (1995) 117, 8258. [67] Kawai, A.; Hara, O.; Hamada, Y.; Shioiri, T., Tetrahedron Lett., (1988) 29, 6331. [68] Baker, R.; Cummings, W. J.; Hayes, J. F.; Kumar, A., J. Chem. Soc., Chem. Commun., (1986), 1237. [69] Thomas, E. J.; Williams, A. C., J. Chem. Soc., Chem. Commun., (1987), 992. [70] Martin, S. F.; Dodge, J. A.; Burgess, L. E.; Limberakis, C.; Hartmann, M., Tetrahedron, (1996) 52, 3229. [71] Nicolaou, K. C.; Liu, J.-J.; Yang, Z.; Ueno, H.; Sorensen, E. J.; Claiborne, C. F.; Guy, R. K.; Hwang, C.-K.; Nakada, M.; Nantermet, P. G., J. Am. Chem. Soc., (1995) 117, 634. [72] King, S. A.; Pipik, B.; Thompson, A. S.; DeCamp, A.; Verhoeven, T. R., Tetrahedron Lett., (1995) 36, 4563. [73] Shing, T. K. M.; Jiang, Q.; Mak, T. C. W., J. Org. Chem., (1998) 63, 2056. [74] Rücker, C., Chem. Rev., (1995) 95, 1009. [75] Ogilvie, K. K.; Thompson, E. A.; Quilliam, M. A.; Westmore, J. B., Tetrahedron Lett., (1974), 2865. [76] Cunico, R. F.; Bedell, L., J. Org. Chem., (1980) 45, 4797. [77] Frye, S. V.; Eliel, E. L., Tetrahedron Lett., (1986) 27, 3223. [78] Barden, D. J.; Fleming, I., Chem. Commun., (2001), 2366. [79] Hagiwara, H.; Inome, K.; Uda, H., J. Chem. Soc., Perkin Trans. 1, (1995), 757. [80] Burke, S. D.; Austad, B. C.; Hart, A. C., J. Org. Chem., (1998) 63, 6770. [81] Wender, P. A.; Badham, N. F.; Conway, S. P.; Floreancig, P. E.; Glass, T. E.; Houze, J. B.; Krauss, N. E.; Lee, D.; Marquess, D. G.; McGrane, P. L.; Meng, W.; Natchus, M. G.; Shuker, A. J.; Sutton, J. C.; Taylor, R. E., J. Am. Chem. Soc., (1997) 119, 2757. [82] Smith, A. B., III.; Condon, S. M.; McCauley, J. A.; Leazer, J. L., Jr.; Leahy, J. W.; Maleczka, R. E., Jr., J. Am. Chem. Soc., (1997) 119, 962. [83] Magnus, P.; Giles, M.; Bonnert, R.; Kim, C. S.; McQuire, L.; Merritt, A.; Vicker, N., J. Am. Chem. Soc., (1992) 114, 3401. [84] Panek, J. S.; Masse, C. E., J. Org. Chem., (1997) 62, 8290. [85] Hanessian, S.; Lavallee, P., Can. J. Chem., (1975) 53, 2975. White, J. D.; Carter, R. G., SOS, (2002) 4, 371. 2002 Georg Thieme Verlag KG
- Page 1 and 2: 4.4.17 Product Subclass 17: Silyl E
- Page 3 and 4: Scheme 1 Silylation with Chlorotrim
- Page 5 and 6: Scheme 4 Silylation with N,O-Bis(tr
- Page 7 and 8: Scheme 8 Cleavage of a Trimethylsil
- Page 9 and 10: Tri-tert-butyl {1S-[1á,3á,4â,5á
- Page 11 and 12: Scheme 13 Cleavage of a Triethylsil
- Page 13 and 14: Scheme 16 Cleavage of Triethylsilyl
- Page 15 and 16: dazole has diminished solubility in
- Page 17 and 18: Scheme 22 Selective Silylation of S
- Page 19 and 20: Scheme 25 Cleavage of Primary and S
- Page 21 and 22: 4.4.17.3.6 Method 6: Cleavage of te
- Page 23 and 24: Scheme 30 Selective Cleavage of a t
- Page 25 and 26: (2Z,4S,5R,6E,8S,9R,10S,12S,13R)-5-(
- Page 27 and 28: 4.4.17.4.1.1 Variation 1: With Trii
- Page 29 and 30: Scheme 38 Cleavage of a Triisopropy
- Page 31 and 32: Scheme 40 Selective Cleavage of a T
- Page 33 and 34: Scheme 43 Monosilylation of Butane-
- Page 35 and 36: Scheme 47 Cleavage of a Bis(tert-bu
- Page 37 and 38: Scheme 50 Selective Cleavage of a t
- Page 39: 4.4.17.6 Other Silyl Ethers FOR PER
tert-Butoxydiphenylsilyl ethers possess stability towards acidic hydrolysis that is<br />
comparable to that of tert-butylmethoxyphenylsilyl ethers. [109] Like the latter group, they<br />
are also quite labile towards fluoride. An advantage of the tert-butoxydiphenylsilyl group<br />
over the tert-butylmethoxyphenylsilyl residue is that it is achiral and, hence, does not produce<br />
diastereomeric silyl ethers.<br />
References<br />
FOR PERSONAL USE ONLY<br />
410 Science of Synthesis 4.4 Silicon Compounds<br />
[1] Greene, T. W.; Wuts, P. G. M., In Protective Groups in Organic Synthesis, 3rd ed., Wiley-Interscience:<br />
New York, (1999); pp 113±148.<br />
[2] Kocien ski, P. J., In Protecting Groups, <strong>Thieme</strong>: Stuttgart, (1994); pp 28±42.<br />
[3] van Look, G.; Simchen, G.; Heberle, J., <strong>Silyl</strong>ating Agents, Fluka Chemie AG: Buchs, Switzerland,<br />
(1995).<br />
[4] Nelson, T. D.; Crouch, R. D., Synthesis, (1996), 1031.<br />
[5] Chen, X.; Hortelano, E. R.; Eliel, E. L.; Frye, S. V., J. Am. Chem. Soc., (1992) 114, 1778.<br />
[6] West, R.; Wilson, L. S.; Powell, D. L., J. Organomet. Chem., (1979) 178,5.<br />
[7] Keck, G. E.; Castellino, S., Tetrahedron Lett., (1987) 28, 281.<br />
[8] Evans, D. A.; Halstead, D. P.; Allison, B. D., Tetrahedron Lett., (1999) 40, 4461.<br />
[9] Wuts, P. G. M.; Bigelow, S. S., J. Org. Chem., (1988) 53, 5023.<br />
[10] Mulzer, J.; Schöllhorn, B., Angew. Chem. Int. Ed. Engl., (1990) 29, 431.<br />
[11] Peters, U.; Bankova, W.; Welzel, P., Tetrahedron, (1987) 43, 3803.<br />
[12] Crich, D.; Ritchie, T. J., Carbohydr. Res., (1990) 197, 324.<br />
[13] Beaucage, S. L.; Iyer, R. P., Tetrahedron, (1992) 48, 2223.<br />
[14] Colvin, E., In Silicon in Organic Synthesis, Butterworth: Boston, (1981); pp 30±39.<br />
[15] Brook, A. G., J. Am. Chem. Soc., (1958) 80, 1886.<br />
[16] Eisch, J. J.; Tasi, M.-R., J. Organomet. Chem., (1982) 225,5.<br />
[17] Brook, A. G.; Pascol, J. D., J. Am. Chem. Soc., (1971) 93, 6224.<br />
[18] Matsuda, I.; Murata, S.; Ishii, Y., J. Chem. Soc., Perkin Trans. 1, (1979), 26.<br />
[19] Gornowicz, G. A.; West, R., J. Organomet. Chem., (1971) 28, 25.<br />
[20] West, R.; Lowe, R.; Stewart, H. F.; Wright, A., J. Am. Chem. Soc., (1971) 93, 282.<br />
[21] Simchen, G.; Pfletschinger, J., Angew. Chem. Int. Ed. Engl., (1976) 15, 428.<br />
[22] Birkofer, L.; Ritter, A.; Bentz, F., Chem. Ber., (1964) 97, 2196.<br />
[23] Sabes, S. F.; Urbanek, R. A.; Forsyth, C. J., J. Am. Chem. Soc., (1998) 120, 2534.<br />
[24] Emde, H.; Domsch, D.; Feger, H.; Frick, U.; Götz, A.; Hergott, H. H.; Hofmann, K.; Kober, W.;<br />
Krägeloh, K.; Oesterle, T.; Steppan, W.; West, W.; Simchen, G., Synthesis, (1982), 1.<br />
[25] Murai, A., Tetrahedron, (1998) 54, 21.<br />
[26] Mai, K.; Patil, G., J. Org. Chem., (1986) 51, 3545.<br />
[27] Churcher, I.; Hallett, D.; Magnus, P., J. Am. Chem. Soc., (1998) 120, 10350.<br />
[28] Galbraith, M. N.; Horn, D. H. S.; Middleton, E. J.; Hackney, R. J., J. Chem. Soc., Chem. Commun.,<br />
(1968), 466.<br />
[29] Horning, M. G.; Boucher, E. A.; Moss, A. M., J. Gas Chromatogr., (1967) 5, 297.<br />
[30] Coleman, R. S.; Kong, J.-S., J. Am. Chem. Soc., (1998) 120, 3538.<br />
[31] Nicolaou, K. C.; Xu, J. Y.; Kim, S.; Pfefferkorn, J.; Ohshima, T.; Vourloumis, D.; Hosokawa, S.,<br />
J. Am. Chem. Soc., (1998) 120, 8661.<br />
[32] Krohn, K.; Micheel, J., Tetrahedron, (1998) 54, 4827.<br />
[33] Oka, T.; Fujiwara, K.; Murai, A., Tetrahedron, (1998) 54, 21.<br />
[34] Wender, P. A.; Jesudason, C. D.; Nakahira, H.; Tamura, N.; Tebbe, A. L.; Ueno, Y., J. Am. Chem. Soc.,<br />
(1997) 119, 12976.<br />
[35] Hart, T. W.; Metcalfe, D. A.; Scheinmann, F., J. Chem. Soc., Chem. Commun., (1979), 156.<br />
[36] Roush, W. R.; Russo-Rodriguez, S., J. Org. Chem., (1987) 52, 598.<br />
[37] Shimizu, S.; Nakamura, S.; Nakada, M.; Shibasaki, M., Tetrahedron, (1996) 52, 13363.<br />
[38] Stoermer, D.; Caron, S.; Heathcock, C., J. Org. Chem., (1996) 61, 9115.<br />
[39] Evans, D. A.; Ratz, A. M.; Huff, B. E.; Sheppard, G. S., J. Am. Chem. Soc., (1995) 117, 3448.<br />
[40] Heathcock, C. H.; Young, S. D.; Hagen, J. P.; Pilli, R.; Badertscher, U., J. Org. Chem., (1985) 50, 2095.<br />
[41] Evans, D. A.; Kim, A. S.; Metternich, R.; Novack, V. J., J. Am. Chem. Soc., (1998) 120, 5921.<br />
[42] Peishoff, C. E.; Jorgensen, W., J. Org. Chem., (1983) 48, 1970.<br />
White, J. D.; Carter, R. G., SOS, (2002) 4, 371. 2002 Georg <strong>Thieme</strong> Verlag KG
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