The electron rich C-C double bond of silyl enol ethers is extremely susceptible to attack by electrophiles. 4095 (1979). Am. Chem. 1213 (1980), Paterson, I., Fleming, I.: Tetrahedron Lett. 4291 (1980), Creger, P.L. Soc. 429 (1979), Klein, J., Levene, R., Dunkelblum, E.: Tetrahedron Lett. 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). This service is more advanced with JavaScript available, Silicon Reagents for Organic Synthesis 160.153.197.168. reaction with TBAF (fluoride ions) gives the desired product after 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. 578 (1979), Conia, J.M., Barnier, J.P.: Tetrahedron Lett. 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. 259 (1978), Kuwajima, I., Abe, T., Minami, N.: Chem. 1433 (1981). Jung, M.E., McCombs, C.A. 2033 (1980), Kelly, L.F., Narula, A.S., Birch, A.J. Chem. : Zhur. Yamamoto, Y., Maruyama, K.: Tetrahedron Lett. Chem. Trost, B.M., Curran, C.P. Silyl enol ethers react with alcohols in a similar manner to alkyl enol ethers to form acetals <73JOC3935, 82S1089 >. Danishefsky, S., Kitahara, T., McKee, R., Schuda, P.F. Rasmussen, J.K., Hassner, A.: J. Org. Chem. Lazukina, L.A., Kukhar, V.P., Pesotskaya, G.V. Soc. Synthesis of α-hydroxy ketones, The synthesis of α-hydroxy ketones is achieved by reaction of silyl enol 1674 (1976). Aqueous work up or reaction with TBAF (fluoride ions) gives the desired product after desilylation . 9 ) or to the silyl enol ether (e.g. Relief of the epoxide ring strain drives the rearrangement Part of Springer Nature. Am. Soc. 1171 (1981). Reactions and uses. 2745 (1980), Kuwajima, I., Kato, M., Mori, A.: Tetrahedron Lett. Am. Comm. Chem. 3779 (1980). Soc. Chem. Reetz, M.T., Schwellnus, K.: Tetrahedron Lett. Larson, G.L., Hernandez, E., Alonso, C., Nieves, I.: Tetrahedron Lett. Schreiber, J., Maag, H., Hashimoto, N., Eschenmoser, A.: Angew. Rasmussen, J.K., Hassner, A.: Tetrahedron Lett. 993 (1979), Paterson, I., Price, L.G. These reactions may be directed by substrate stereochemistry, giving rise to stereoselective ring-contracted product formation. The synthesis of α-hydroxy ketones is achieved by reaction of silyl enol ethers with mCPBA, with subsequent rearrangement. 2833 (1981), Danishef sky, S., Guingant, A., Prisbylla, M.: Tetrahedron Lett. : J. 1658 (1972), Mukaiyama, T., Ishida, A.: Chem. 1455 (1978). Donaldson, R.E., Fuchs, P.L. with migration of the silyl group to give the silylated α-hydroxy ketone Chem. Download preview PDF. product. Murata, S., Suzuki, M., Noyori, R.: J. Mukaiyama, T., Narasaka, K., Banno, K.: Chem. Comm. : Tetrahedron Lett. Chem. Soc. Chem. Reetz, M.T., Maier, W.F. Chem. : Tetrahedron Lett. Lett. Chem. Khim. Electrophiles regiospecifically attack the C-C double bond of trimethylsilyl enol ethers to yield a trimethylsilyloxy stabilized carbocation. Khim. Aza-Rubottom Oxidation: Synthetic Access to Primary α-Aminoketones All yields are isolated yields after chromatographic purification unless otherwise stated. Especially intramolecular reactions under participation of an enol ether function have never been specifically surveyed. 2019, 989 (1975), Asaoka, M., Yanagida, N., Takei, H. Tetrahedron Lett. 1011 (1973). Fitjer, L., Conia, J.M. Chem. : Tetrahedron Lett. : Angew. 741 (1975), Ojima, I., Yoshida, K., Inaba, S.I. Mechanism of the Rubottom Oxidation. : J. Org. Not logged in Lett. Soc. Lett. Over 10 million scientific documents at your fingertips. Chem. Am. Am. 1167 (1975), Narasaka, K., Soai, K., Mukaiyama, T.: Chem. Reactions performed using 0.5 mmol of silyl enol ether starting material. 4491 (1967), Rathke, M.W., Sullivan, D.F. Chim. Nauk SSSR, Ser. Reetz, M.T., Chatziiosifidis, I., Löwe, U., Maier, W.F. Chem. : J. Lett. Murai, S., Kuroki, Y., Hasegawa, K., Tsutsumi, S.: J. Chem. Murai, S., Koroki, Y., Hasegawa, K., Tsutsumi, S.: J. Chem. Both cyclic and acyclic ketones gave silyl enol ethers in high yield, whose stereochemistry showed that the formation of thermodynamically stable isomers was favored. Am. 531 (1975), Kuwajima, I., Kato, M.: Tetrahedron Lett. The enol ether double bond is epoxidized by the peracid. J. Chem. Minami, N., Abe, T., Kuwajima, I.: J. Organometal. 993 (1976), Kuwajima, I., Matsumoto, K., Inoue, T.: Chem. : Chem. Cite as. 2829 (1981), Paterson, I., Price, L.G. Ito, Y., Nakatsuka, M., Saegusa, T.: J. Org. Aqueous work up or 805 (1980), Miyano, S., Hokari, H., Mori, A., Hashimoto, N.: Chem. 1223 (1974). Not affiliated 1427 (1979). Ed. 1). 2749 (1978), Kraus, G.A., Shimagaki, M.: Tetrahedron Lett. Chem. Soc., The Rubottom oxidation is a useful, high-yielding chemical reaction between silyl enol ethers and peroxyacids to give the corresponding α-hydroxy carbonyl product. Obsh. 623 (1980). : Zhur. © 2020 Springer Nature Switzerland AG. : Tetrahedron Lett. Mukaiyama, T., Banno, K., Narasaka, K.: J. Banno, K., Mukaiyama, T.: Chem. Am. Fr. Z. Zhou, Q.-Q. Chem. 3779 (1980), Murai, S., Koroki, Y., Aya, T., Sonoda, N., Tsutsumi, S.: J. Chem. ethers with mCPBA, with subsequent rearrangement. Chem. 163 (1976), Kita, Y., Segawa, J., Haruta, J., Fujii. Syn. Chem. 15 (1974). Asaoka, M., Sugimura, N., Takei, H.: Bull. Kuwajima, I., Kato, M., Mori, A.: Tetrahedron Lett. Lett. Lett. Soc. Khim. : J. Org. 2179 (1977), Paterson, I., Fleming, I.: Tetrahedron Lett. 463 (1976), Sato, T., Abe, T., Kuwajima, I.: Tetrahedron Lett. Ed. Lett. 946 (1972). Am. Lett. Soc. Ed. Purlachenko, G.S., Mal’tsev, V.V., Baukov, Yu.I., Lutsenko, I.F. : Synthesis, 941 (1980). : Tetrahedron Lett. Miyashita, M., Yanami, T., Yoshikoshi, A.: J. Obsh. Chem. Reetz, M.T., Maier, W.F., Schwellnus, K., Chatziiosifidis, I.: Angew. The photochemically induced diastereoselective formation of 3‐(silyloxy)oxetanes from silyl enol ethers and aromatic aldehydes was studied. 429 (1977), Ojima, I., Yoshida, K., Inaba, S.I. Chem. Soc. Nakamura, E., Murofushi, T., Shimizu, M., Kuwajima, I.: J. 741 (1972). Ryu, I., Murai, S., Niwa, I., Sonoda, N.: Synthesis, 874 (1977), Kita, Y., Segawa, J., Harata, J., Fujii, T., Tamura, Y.: Tetrahedron Lett.

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