シャープレス酸化とは - わかりやすく解説 Weblio辞書

ウィキペディア

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シャープレス酸化

出典: フリー百科事典『ウィキペディア（Wikipedia）』 (2024/01/05 03:37 UTC 版)

シャープレス酸化（シャープレスさんか、英: Sharpless oxidation）とは、遷移金属触媒を使用してヒドロペルオキシドによりアリルアルコール誘導体の二重結合をエポキシ化する化学反応のことである。

脚注

^ ^a ^b ^c Katsuki, T.; Sharpless, K. B. (1980). “The first practical method for asymmetric epoxidation”. J. Am. Chem. Soc. 102 (18): 5974. doi:10.1021/ja00538a077.
^ Hill, J. G.; Sharpless, K. B.; Exon, C. M.; Regenye, R. (1985). "Enantioselective Epoxidation of Allylic Alcohols: (2S,3S)-3-Propyloxiranemethanol". Organic Syntheses (英語). 63: 66. doi:10.15227/orgsyn.063.0066。; Collective Volume, vol. 7, p. 461
^ ^a ^b Uetikon, C. F. (1986). Synthesis (Stuttgart): 88–116.
^ Finn, M. G.; Sharpless, K. B. (1991). “Mechanism of asymmetric epoxidation. 2. Catalyst structure”. J. Am. Chem. Soc. 113: 113–126. doi:10.1021/ja00001a019.
^ Takano, S.; Iwabuchi, Y.; Ogasawara, K. (1991). “Inversion of enantioselectivity in the kinetic resolution mode of the Katsuki-Sharpless asymmetric epoxidation reaction”. J. Am. Chem. Soc. 113 (7): 2786–2787. doi:10.1021/ja00007a082.
^ Kitano, Y.; Matsumoto, T.; Sato, F. (1988). “A highly efficient kinetic resolution of γ- and β- trimethylsilyl secondary allylic alcohols by the sharpless asymmetric epoxidation”. Tetrahedron 44 (13): 4073–4086. doi:10.1016/S0040-4020(01)86657-6.
^ Martin, V.; Woodard, S.; Katsuki, T.; Yamada, Y.; Ikeda, M.; Sharpless, K. B. (1981). “Kinetic resolution of racemic allylic alcohols by enantioselective epoxidation. A route to substances of absolute enantiomeric purity?”. J. Am. Chem. Soc. 103 (20): 6237–6240. doi:10.1021/ja00410a053.
^ Rossiter, B.; Katsuki, T.; Sharpless, K. B. (1981). “Asymmetric epoxidation provides shortest routes to four chiral epoxy alcohols which are key intermediates in syntheses of methymycin, erythromycin, leukotriene C-1, and disparlure”. J. Am. Chem. Soc. 103 (2): 464–465. doi:10.1021/ja00392a038.
^ Sharpless, K. B.; Behrens, C. H.; Katsuki, T.; Lee, A. W. M.; Martin, V. S.; Takatani, M.; Viti, S.M.; Walker, F. J. et al. (1983). “Stereo and regioselective openings of chiral 2,3-epoxy alcohols. Versatile routes to optically pure natural products and drugs. Unusual kinetic resolutions”. Pure Appl. Chem. 55 (4): 589. doi:10.1351/pac198855040589.
^ Henbest, H. B.; Wilson, R. A. L. (1957). “376. Aspects of stereochemistry. Part I. Stereospecificity in formation of epoxides from cyclic allylic alcohols”. J. Che. Soc.: 1958. doi:10.1039/jr9570001958.
^ Chamberlain, P.; Roberts, M. L.; Whitham, G. H. (1970). “Epoxidation of allylic alcohols with peroxy-acids. Attempts to define transition state geometry”. J. Chem. Soc. B: 1374. doi:10.1039/j29700001374.
^ Weyerstahl, Peter; Marschall-Weyerstahl, Helga; Penninger, Josef; Walther, Lutz (1987). “Terpenes and terpene derivatives-22”. Tetrahedron 43 (22): 5287–5298. doi:10.1016/S0040-4020(01)87705-X.
^ McKittrick, Brian A.; Ganem, Bruce (1985). “Syn-stereoselective epoxidation of allylic ethers using CF₃CO₃H”. Tetrahedron Lett. 26 (40): 4895–4898. doi:10.1016/S0040-4039(00)94979-7. ISSN 00404039.
^ Hoveyda, Amir H.; Evans, David A.; Fu, Gregory C. (1993). “Substrate-directable chemical reactions”. Chem. Rev. 93 (4): 1307–1370. doi:10.1021/cr00020a002.
^ Houk, K.; Paddon-Row, M.; Rondan, N.; Wu, Y.; Brown, F.; Spellmeyer, D.; Metz, J.; Li, Y et al. (1986). “Theory and modeling of stereoselective organic reactions”. Science 231 (4742): 1108–1117. doi:10.1126/science.3945819.
^ Adam, Waldemar; Wirth, Thomas (1999). “Hydroxy Group Directivity in the Epoxidation of Chiral Allylic Alcohols: Control of Diastereoselectivity through Allylic Strain and Hydrogen Bonding”. Acc. Chem. Res. 32 (8): 703–710. doi:10.1021/ar9800845. ISSN 0001-4842.
^ Mihelich, Edward D. (1979). “Vanadium-catalyzed epoxidations. I. A new selectivity pattern for acyclic allylic alcohols”. Tetrahedron Lett. 20 (49): 4729–4732. doi:10.1016/S0040-4039(01)86695-8.
^ Rossiter, B.E.; Verhoeven, T.R.; Sharpless, K.B. (1979). “Stereoselective epoxidation of acyclic allylic alcohols. A correction of our previous work”. Tetrahedron Lett. 20 (49): 4733–4736. doi:10.1016/S0040-4039(01)86696-X.
^ Narula, Acharan S. (1982). “Stereoselective introduction of chiral centres in acylic precursors: a probe into the transition state for V⁵⁺-catalyzed t-butylhydroperoxide (TBHP) epoxidation of acyclic allylic alcohols and its synthetic implications”. Tetrahedron Lett. 23 (52): 5579–5582. doi:10.1016/S0040-4039(00)85899-2.
^ Darby, A. C.; Henbest, H. B.; McClenaghan I. (1962). Chem. Ind. (London): 462-463.
^ Cragg, G. M. L.; Meakins, G. D. (1965). “366. Steroids of unnatural configuration. Part IX. Oxidation of 9α-lumisterol (pyrocalciferol) and 9β-ergosterol (isopyrocalciferol) with perbenzoic acid”. J. Chem. Soc. 0 (0): 2054–2063. doi:10.1039/JR9650002054.
^ Johnson, Mark R.; Kishi, Yoshito (1979). “Cooperative effect by a hydroxy and ether oxygen in epoxidation with a peracid”. Tetrahedron Lett. 20 (45): 4347–4350. doi:10.1016/S0040-4039(01)86585-0.
^ Mihelich, Edward D.; Daniels, Karen; Eickhoff, David J. (1981). “Vanadium-catalyzed epoxidations. 2. Highly stereoselective epoxidations of acyclic homoallylic alcohols predicted by a detailed transition-state model”. J. Am. Chem. Soc. 103 (25): 7690–7692. doi:10.1021/ja00415a067.
^ Itoh, Takashi; Jitsukawa, Koichiro; Kaneda, Kiyotomi; Teranishi, Shiichiro (1979). “Vanadium-catalyzed epoxidation of cyclic allylic alcohols. Stereoselectivity and stereocontrol mechanism”. J. Am. Chem. Soc. 101 (1): 159–169. doi:10.1021/ja00495a027.
^ Sharpless, K. B.; Michaelson, R. C. (1973). “High stereo- and regioselectivities in the transition metal catalyzed epoxidations of olefinic alcohols by tert-butyl hydroperoxide”. J. Am. Chem. Soc. 95 (18): 6136–6137. doi:10.1021/ja00799a061.