22, J. Wiley, New York, New York: 1975, Saigo, K., Osaki, M., Mukaiyama, T.: Chem. Cite as. Ito, Y., Nakatsuka, M., Saegusa, T.: J. Org. T., Tamura, Y.: Tetrahedron Lett. The electron rich C-C double bond of silyl enol ethers is extremely susceptible to attack by electrophiles. Minami, N., Abe, T., Kuwajima, I.: J. Organometal. Soc. 995 (1979), Paterson, I., Fleming, I.: Tetrahedron Lett. Especially intramolecular reactions under participation of an enol ether function have never been specifically surveyed. Soc. Soc. Sign in to download full-size image. Lett. The Mukaiyama aldol addition is an organic reaction and a type of aldol reaction between a silyl enol ether and an aldehyde or formate. 1433 (1981). Rasmussen, J.K., Hassner, A.: J. Org. Chem. Shvarts, I.S., Yarovenko, V.N., Krayushkin, M.M., Novikov, S.S., Sevost’yanova, V.V. 993 (1976), Kuwajima, I., Matsumoto, K., Inoue, T.: Chem. 4005 (1975), https://doi.org/10.1007/978-3-642-68661-0_12, Reactivity and Structure Concepts in Organic Chemistry. Int. Rasmussen, J.K., Hassner, A.: Tetrahedron Lett. Part of Springer Nature. : Chem. Chem. Murai, S., Koroki, Y., Hasegawa, K., Tsutsumi, S.: J. Chem. with migration of the silyl group to give the silylated α-hydroxy ketone 39, 1785 (1974), Blanco, L., Amice, P., Conia, J.M. 578 (1979), Conia, J.M., Barnier, J.P.: Tetrahedron Lett. Chem. Chem. In some cases, when subjected to the optimized reaction conditions for transfer hydrogenation, significant quantities of silyl enol ether decomposition was observed, most likely due to the presence of a strong Lewis acid, B (C 6 F 5) 3, and the elevated reaction temperature (130 °C). Akad. 946 (1972). : Tetrahedron Lett. Koroki, Y., Murai, S., Sonoda, N., Tsutsumi, S.: Organometal. Mukaiyama aldol addition and Michael reactions. Danishefsky, S., Prisbylla, M., Lipisko, B.: Tetrahedron Lett. Khim. 4491 (1967), Rathke, M.W., Sullivan, D.F. Murata, S., Suzuki, M., Noyori, R.: J. Download preview PDF. : Tetrahedron Lett. Lett. Chem. Int. Chem. Obsh. This service is more advanced with JavaScript available, Silicon Reagents for Organic Synthesis : J. 1223 (1974). : Synthesis, 194 (1976), Chan, T.H., Brownbridge, P.: J. Chem. Evans, D.A., Vogel, E., Nelson, J.V. Murai, S., Hasegawa, K., Sonoda, N.: Angew. Chem. Lazukina, L.A., Kukhar, V.P., Pesotskaya, G.V. 4291 (1980), Creger, P.L. 3779 (1980), Murai, S., Koroki, Y., Aya, T., Sonoda, N., Tsutsumi, S.: J. Chem. 2783 (1973). : J. Usually, the nucleophilic anion associated with the electrophile attacks the silyl center of this intermediate to yield a substituted ketone in which the electrophile is bonded to the α position. Chem. Ber. This process is experimental and the keywords may be updated as the learning algorithm improves. The photochemically induced diastereoselective formation of 3‐(silyloxy)oxetanes from silyl enol ethers and aromatic aldehydes was studied. Lett. Both cyclic and acyclic ketones gave silyl enol ethers in high yield, whose stereochemistry showed that the formation of thermodynamically stable isomers was favored. The reaction was discovered by Teruaki Mukaiyama (1927–2018) in 1973. Davis Oxidation Reuss, R.H., Hassner, A.: J. Org. Lett. Generation of silyl enol ethers from enones enables additional functionality to be introduced ( Scheme 24) < 84TL3805, 85JOC3627 >. 741 (1975), Ojima, I., Yoshida, K., Inaba, S.I. Int. Chem. Syn. In comparison with simple alkenes, enol ethers exhibit enhanced susceptibility to attack by electrophiles such as Bronsted acids. The enol ether double bond is epoxidized Mechanism of the Rubottom Oxidation. Chem. These reactions may be directed by substrate stereochemistry, giving rise to stereoselective ring-contracted product formation. Jung, M.E., McCombs, C.A. 527 (1975), Ishihara, H., Inomata, K., Mukaiyama, T.: Chem. 41 (1979), Kuwajima, I., Matsumoto, K.: Tetrahedron Lett. Related Reactions Reetz, M.T., Maier, W.F., Schwellnus, K., Chatziiosifidis, I.: Angew. Am. 163 (1976), Kita, Y., Segawa, J., Haruta, J., Fujii. Reactions and uses. 429 (1977), Ojima, I., Yoshida, K., Inaba, S.I. Ed. : Tetrahedron Lett. Chem. Mukaiyama, T., Narasaka, K., Banno, K.: Chem. 1519 (1979), Reetz, M.T., Hüttenhain, S.H. Silyl enol ethers react as nucleophiles in many reactions resulting in alkylation, e.g. 3127 (1980), Saigo, K., Osaki, M., Mukaiyama, T.: Chem. Chem. These reactions employ electron-deficient sulfonyl azides, which undergo chemoselective, uncatalyzed [3+2] cycloaddition to the silyl enol ether, followed by loss of dinitrogen, and alkyl migration to give ring-contracted products in good yield. : Tetrahedron Lett. High yields and diastereoselectivities are obtained with a variety of silyl enol ether/aldehyde/Grignard combinations. 76, 6 (1974). Ed. Murata, S., Suzuki, M., Noyori, R.: Tetrahedron Lett. 9) or to the silyl enol ether (e.g. : Izv. Am. Khim. House, H.O., Crumrine, O.S., Teranishi, A.Y., Olmstead, H.D. Lett. Lett. Chim. : Tetrahedron Lett. 1). 319 (1975), Ishida, A., Mukaiyama, T.: Chem. The enol ether double bond is epoxidized by the peracid. Mukaiyama, T., Banno, K., Narasaka, K.: J. Soc. Prilezhaev Reaction Int. Banno, K., Mukaiyama, T.: Chem. Chem. 805 (1980), Miyano, S., Hokari, H., Mori, A., Hashimoto, N.: Chem. Unable to display preview. 1427 (1979). Chem. 2179 (1977), Paterson, I., Fleming, I.: Tetrahedron Lett. Trost, B.M., Curran, C.P. Int. Lett. Soc. 4607 (1980). 1674 (1976). Asaoka, M., Sugimura, N., Takei, H.: Bull. by the peracid. 2829 (1981), Paterson, I., Price, L.G. desilylation. Soc. : J. Org. Chem. 2833 (1981), Danishef sky, S., Guingant, A., Prisbylla, M.: Tetrahedron Lett. Chem. Scheme 24. : Angew. Comm. 2019, Am. 1658 (1972), Mukaiyama, T., Ishida, A.: Chem. Soc., Transformation of ketones to silyl enol ethers using (trimethylsilyl)diethylamine and methyl iodide is described. Ed. Japan. 141, 2242-2246. Larson, G.L., Hernandez, E., Alonso, C., Nieves, I.: Tetrahedron Lett. Ed. Cheng, L. Kürti, J. 1171 (1981). ethers with mCPBA, with subsequent rearrangement. Lett. Z. Zhou, Q.-Q. Donaldson, R.E., Fuchs, P.L. Lett. Wissner, A.: Tetrahedron Lett. : Chem. Chem. The synthesis of α-hydroxy ketones is achieved by reaction of silyl enol ethers with mCPBA, with subsequent rearrangement. It is shown that many heteroatom‐ and double bond‐containing substituents (ether, ester, acetal, amide, alkene) withstand the reaction conditions and may therefore be attached either to the carbonyl compound (e.g. : Angew. Aqueous work up or reaction with TBAF (fluoride ions) gives the desired product after desilylation . Synthesis of α-hydroxy ketones, The synthesis of α-hydroxy ketones is achieved by reaction of silyl enol Chem. Nakamura, E., Murofushi, T., Shimizu, M., Kuwajima, I.: J. Reetz, M.T., Maier, W.F. Chem. Ketone super silyl enol ethers are shown to be excellent nucleophiles in the Mukaiyama aldol reaction as well as in sequential one-pot diastereoselective reactions. Chem. Danishefsky, S., Kitahara, T., McKee, R., Schuda, P.F. Lett. Reetz, M.T., Chatziiosifidis, I., Löwe, U., Maier, W.F. Am. Comm. Narasaka, K., Soai, K., Aikawa, Y., Mukaiyama, T.: Bull. 1167 (1975), Narasaka, K., Soai, K., Mukaiyama, T.: Chem. 2845 (1972), Larson, G.L., Hernandez, D., Hernandez, A.: J. Organometal. : J. Org. Purlachenko, G.S., Mal’tsev, V.V., Baukov, Yu.I., Lutsenko, I.F. Reactions performed using 0.5 mmol of silyl enol ether starting material. pp 206-227 | Am. 1011 (1973). J. Chem. Reetz, M.T., Maier, W.F., Chatziiosifidis, I., Giannis, A., Heimbach, H., Löwe, U.: Chem. The photochemically induced diastereoselective formation of 3‐(silyloxy)oxetanes from silyl enol ethers and aromatic aldehydes was studied.

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