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For preliminary accounts of the present work See: (a), (b) Noyori, R.; Nishida, I.; Sakata, J. Tetrahedron Lett. 1980, 21, 2085. (c) Noyori, R.; Nishida, I.; Sakata, J.J. Am. Chem. Soc. 1981, 103, 2106.
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For preliminary accounts of the present work See: (a) Noyori, R.; Nishida, I.; Sakata, J.; Nishizawa, M. J. Am. Chem. Soc. 1980, 102, 1223. (b) Noyori, R.; Nishida, I.; Sakata, J. Tetrahedron Lett. 1980, 21, 2085. (c) Noyori, R.; Nishida, I.; Sakata, J.J. Am. Chem. Soc. 1981, 103, 2106.
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Reviews: House, H.O. “Modern Synthetic Reactions”, 2nd ed.; Benjamin: Menlo Park, CA, 1972;Chapters 9-12. d'Angelo, J. Tetrahedron 1976, 32, 2979. Stowell, J.C. “Carbanions in Organic Synthesis”; Wiley: New York, 1979; Chapter 5.
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Kuwajima, I.; Nakamura, E. J. Am. Chem. Soc. 1975, 97, 3257. Kuwajima, I.; Nakamura, E.; Shimizu, M.J. Am. Chem. Soc. 1982, 104, 1025.
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Nakamura, E.; Shimizu, M.; Kuwajima, I.; Sakata, J.; Yokoyama, K.; Noyori, R. submitted for publication, (c) Kleshick, W.A.; Buse, C.T.; Heathcock, C.H.J. Am. Chem. Soc. 1977, 99, 247.
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(a) Noyori, R.; Yokoyama, K.; Sakata, J.; Kuwajima, I.; Nakamura, E.; Shimizu, M. J. Am. Chem. Soc. 1977, 99, 1265. (b) Nakamura, E.; Shimizu, M.; Kuwajima, I.; Sakata, J.; Yokoyama, K.; Noyori, R. submitted for publication, (c) Kleshick, W.A.; Buse, C.T.; Heathcock, C.H.J. Am. Chem. Soc. 1977, 99, 247.
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DePuy, C.H.; Bierbaum, V.M.; Flippin L.A.; Grabowski, J.J.; King, G.K.; Schmitt, R.J.J. Am. Chem. Soc. 1979, 101, 6443. (c) Vedejs, E.; Matrinez, G.R.J. Am. Chem. Soc. 1979, 101, 6452. (d) Vedejs, E.; Martinez, G.R.J. Am. Chem. Soc. 1980, 102, 7993 and references cited therein.
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Middleton, W.J. U.S. Patent 3940402, 1976.
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Middleton, W.J.1
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85023277233
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Disadvantages include the high cost and the suscepttbility of the TAS moiety to a base-promoted fragmentation
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Disadvantages include the high cost and the suscepttbility of the TAS moiety to a base-promoted fragmentation.
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33947088006
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(a) House, H.O.; Auerbach, R.A.; Gall, M.; Peet, N.P. J. Org. Chem. 1973, 38, 514. (b) House, H.O.; Prabhu, A.V.; Phillips, W.V.J. Org. Chem. 1976, 41, 1209.
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Clark, H.C.; Dixon, K.R.; Nicolson, J.G. Inorg. Chem. 1969, 8, 450. (c) Marat, R.K.; Janzen, A.F. Can. J. Chem. 1977, 55, 1167, 3845. (d) Murphy, M.K.; Beauchamp, J.L.J. Am. Chem. Soc. 1977, 99, 4992. (e) Sullivan, S.A.; DePuy, C.H.; Damrauer, R.J. Am. Chem. Soc. 1981, 103, 480. Trifluorotrimethyl-siliconate may also form under the present conditions: Moscony, J.J.; MacDiarmid, A.G.J. Chem. Soc, Chem. Commun. 1965, 307.
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(a) Klanberg, F.; Muetterties, E.L. Inorg. Chem. 1968, 7, 155. (b) Clark, H.C.; Dixon, K.R.; Nicolson, J.G. Inorg. Chem. 1969, 8, 450. (c) Marat, R.K.; Janzen, A.F. Can. J. Chem. 1977, 55, 1167, 3845. (d) Murphy, M.K.; Beauchamp, J.L.J. Am. Chem. Soc. 1977, 99, 4992. (e) Sullivan, S.A.; DePuy, C.H.; Damrauer, R.J. Am. Chem. Soc. 1981, 103, 480. Trifluorotrimethyl-siliconate may also form under the present conditions: Moscony, J.J.; MacDiarmid, A.G.J. Chem. Soc, Chem. Commun. 1965, 307.
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85023353955
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Some concentration dependency was observed. However, further precise measurements at lower concentration were not made because of the moisture and air sensitivity of 5
-
Some concentration dependency was observed. However, further precise measurements at lower concentration were not made because of the moisture and air sensitivity of 5.
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Wiley-Interscience: New York, pp. 22-24, 136-144. Levy, G.C.; Lichter, R.L.; Nelson, G.L. “Carbon-13 Nuclear Magnetic Resonance Spectroscopy”, 2nd ed.; Wiley-Interscience: New York, 1980; Chapter 6. Stothers, J.B. “Carbon-13 NMR Spectroscopy”; Academic Press: New York, 1972;, Bates, R.B.; Brenner, S.; Cole, C.M.; Davidson, E.W.; Forsythe, G.D.; McCombs, D.A.; Roth, A.S.J. Am. Chem. Soc. 1973, 95, 926. Ford, W.T.; Newcomb, M.J. Am. Chem. Soc. 1974, 96, 309. O'Brien, D.H.; Hart, A.J.; Russell, C.R.J. Am. Chem. Soc. 1975, 97, 4410. O'Brien, D.H.; Russell, C.R.; Hart, A.J.J. Am. Chem. Soc. 1976, 98, 7427. van Dongen, J.P.C.M.; van Dijkman, H.W.D.; deBie, M.J.A. Reel. Trav. Chim. Pays-Bas 1974, 93, 29. Bywater, S.; Lachance, P.; Worsford, D.J.J. Phys. Chem. 1975, 79, 2148. Edlund, U. Org. Magn. Resort. 1977, 9, 593. Fraenkel, G.; Fraenkel, A.M.; Geckle, M.J.; Schloss, F.J. Am. Chem. Soc. 1979, 101, 4745.
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Abstracts of Papers
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Farnham, W.B.; Middleton, W.J.; Sam, D.J. “Abstracts of Papers”, 172nd National Meeting of the American Chemical Society, San Francisco, CA, Aug 30-Sept 3, 1976; American Chemical Society: Washington, D.C., 1976; ORGN 46. Cowley, A.H.; Pagel, D.J.; Walker, M.L.J. Am. Chem. Soc. 1978, 100, 7065.
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Farnham, W.B.1
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85023318010
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Since ‘H NMR spectra of phenol and phenyl trimethylsilyl ether exhibit similar signal patterns in the aromatic region, use of the enol silyl ether as a neutral model compound would not be unreasonable
-
Since ‘H NMR spectra of phenol and phenyl trimethylsilyl ether exhibit similar signal patterns in the aromatic region, use of the enol silyl ether as a neutral model compound would not be unreasonable.
-
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21
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0040323749
-
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Planar structures are assumed for the models 6 and 7, although for the actual compounds 1 and 5 two ortho and meta positions are equivalent in the NMR time scale. The structures for the calculations are derived by using optimized bond lengths
-
Planar structures are assumed for the models 6 and 7, although for the actual compounds 1 and 5 two ortho and meta positions are equivalent in the NMR time scale. The structures for the calculations are derived by using optimized bond lengths (MINDO/3) for vinyloxy anion (1.374 A for C-C and 1.257 A for C-O) and standard parameters for other fragments: Baird, N.C.; Dewar, M.J.S.J. Chem. Phys. 1969, 50, 1262. Bingham, R.C.; Dewar, M.J.S.; Lo, D.H.J. Am. Chem. Soc. 1975, 97, 1285.
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85023396863
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This may be due to magnetic anisotropy of the oxygen atom
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This may be due to magnetic anisotropy of the oxygen atom.
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DePalma, V.M.; Arnett, E.M.J. Am. Chem. Soc. 1978, 100, 3514.
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0001195973
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Change in electron distribution is not the sole factor controlling the magnitude of the chemical shift change. The chemical shift for charged species is highly dependent on the nature of substituents, particularly heteroatoms
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Change in electron distribution is not the sole factor controlling the magnitude of the chemical shift change. The chemical shift for charged species is highly dependent on the nature of substituents, particularly heteroatoms: Olah, G.A.; White, A.M.J. Am. Chem. Soc. 1968, 90, 1884. Olah, G.A.; Halpern, Y.; Mo, Y.K.; Liang, G. J. Am. Chem. Soc. 1972, 94, 3554.
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85023385320
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ref 6
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For the quaternary ammonium fluoride promoted reaction, see
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For the quaternary ammonium fluoride promoted reaction, see ref 6.
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For photostimulated SRN1 reaction of potassium enolates See:, Komin, A.P.; Wolfe, J.F.J. Org. Chem. 1977, 42, 2481. Bunnett, J.F.; Bard, R.R.J. Org. Chem. 1978, 43, 1019. An ESR signal was observed in the reaction of a lithium enolate and methyl p-nitrobenzenesulfonate in dioxane: Jackman, L.M.; Lange, B.C.J. Am. Chem. Soc. 1981, 103, 4494.
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For photostimulated SRN1 reaction of potassium enolates See: Bunnett, J.F.; Sundberg, J.E. J. Org. Chem. 1976, 41, 1702. Komin, A.P.; Wolfe, J.F.J. Org. Chem. 1977, 42, 2481. Bunnett, J.F.; Bard, R.R.J. Org. Chem. 1978, 43, 1019. An ESR signal was observed in the reaction of a lithium enolate and methyl p-nitrobenzenesulfonate in dioxane: Jackman, L.M.; Lange, B.C.J. Am. Chem. Soc. 1981, 103, 4494.
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85023299664
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ref 7
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For the quaternary ammonium fluoride catalyzed aldol reaction, see
-
For the quaternary ammonium fluoride catalyzed aldol reaction, see ref 7.
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0003145547
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Reviews on aldol reactions:, House, H.O. “Modern Synthetic Reactions”, 2nd ed.; Benjamin: Menlo Park, CA, 1972; pp. 629-682.
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Reviews on aldol reactions: Nielsen, A.T.; Houlihan, W. J. Org. React. 1968, 16, 1. House, H.O. “Modern Synthetic Reactions”, 2nd ed.; Benjamin: Menlo Park, CA, 1972; pp. 629-682.
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For an excellent review on stereoselective aldol condensations, See: Heathcock, C.H. “Comprehensive Carbanion Chemistry”; Durst, T., Buncel, E., Eds.; Elsevier: Amsterdam, 1981; Vol. II, Chapter 4.
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(a) Li+: Kleschick, W.A.; Buse, C.T.; Heathcock, C.H. J. Am. Chem. Soc. 1977, 99, 247. Buse, C.T.; Heathcock, C.H.J. Am. Chem. Soc. 1977, 99, 8109. Heathcock, C.H.; White, C.T.J. Am. Chem. Soc. 1979, 101, 7076. Heathcock, C.H.; Pirrung, M.C.; Buse, C.T.; Hagen, J.P.; Young, S.D.; Sohn, J.E.J. Am. Chem. Soc. 1979, 101, 7077. Heathcock, C.H.; Buse, C.T.; Kleschick, W.A.; Pirrung, M.C.; Sohn, J.E.; Lampe, J.J. Org. Chem. 1980, 45, 1066. Pirrung, M.C.; Heathcock, C.H.J. Org. Chem. 1980, 45, 1727. Heathcock, C.H.; Young, S.D.; Hagen, J.P.; Pirrung, H.C.; White, C.T.; VanDerveer, D.J. Org. Chem. 1980, 45, 3846. Heathcock, C.H.; White, C.T.; Morrison, J.J.; VanDerveer, D.J. Org. Chem. 1981, 46, 1296. (b) Li+: Dubois, J.E.; Fellmann, P. Tetrahedron Lett. 1975, 1225. Meyers, A.I.; Reider, P.J.J. Am. Chem. Soc. 1979, 101, 2501. Masamune, S.; Ali, S.A.; Snitman, D.L.; Garvey, D.S. Angew. Chem. 1980, 92, 573. (c) Li+, Mg2+, Zn2+: ref 34. (d) Sn2+: Mukaiyama, T.; Stevens, R.W.; Iwasawa, N. Chem. Lett. 1982, 353. Harada, T.; Mukaiyama, T. Chem. Lett. 1982, 467.
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B3+: (a), (b) Mukaiyama, T.; Inoue, T. Chem. Lett. 1976, 559. Inoue, T.; Uchimaru, T.; Mukaiyama, T. Chem. Lett. 1977, 153. Inoue, T.; Mukaiyama, T. Bull. Chem. Soc. Jpn. 1980, 53, 174. (c) Masamune, S.; Van Horn, D.; Brooks, D.W. Tetrahedron Lett. 1979, 1665. Van Horn, D.E.; Masamune, S. Tetrahedron Lett. 1979, 2229. Hirama, M.; Garvey, D.S.; Lu, L.D.-L.; Masamune, S. Tetrahedron Lett. 1979, 3937. Masamune, S.; Choy, W.; Kerdesky, F.A.J.; Imperiali, B.J. Am. Chem. Soc. 1981, 103, 1566. Masamune, S.; Hirama, M.; Mori, S.; Ali, S.A.; Garvey, D.S.J. Am. Chem. Soc. 1981, 103, 1568. Choy, W.; Ma, P.; Masamune, S. Tetrahedron Lett. 1981, 22, 3555. (d) Evans, D.A.; Vogel, E.; Nelson, J.V.J. Am. Chem. Soc. 1979, 101, 6120. Evans, D.A.; Nelson, J.V.; Vogel, E.; Taber, T.R.J. Am. Chem. Soc. 1981, 103, 3099. (e) Wada, M. Chem. Lett. 1981, 153.
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37
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0006390865
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Al3+: (a), (b) Maruoka, K.; Hashimoto, S.; Kitagawa, Y.; Yamamoto, H.; Nozaki, H.J. Am. Chem. Soc. 1977, 99, 7705. Nozaki, H.; Oshima, K.; Takai, K.; Ozawa, S. Chem. Lett. 1979, 379.
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38
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0000999555
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Ti4+: (a), Mukaiyama, T.; Banno, K.; Narasaka, K.J. Am. Chem. Soc. 1974, 96, 7503. (b) Chan, T.H.; Aida, T.; Lau, P.W.K.; Gorys, V.; Harpp, D.N. Tetrahedron Lett. 1979, 4029. (c) Reetz, M.T.; Peter, R. Tetrahedron Lett. 1981, 22, 4691.
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Ti4+: (a) Mukaiyama, T.; Narasaka, K.; Banno, K. Chem. Lett. 1973, 1011. Mukaiyama, T.; Banno, K.; Narasaka, K.J. Am. Chem. Soc. 1974, 96, 7503. (b) Chan, T.H.; Aida, T.; Lau, P.W.K.; Gorys, V.; Harpp, D.N. Tetrahedron Lett. 1979, 4029. (c) Reetz, M.T.; Peter, R. Tetrahedron Lett. 1981, 22, 4691.
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39
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0000244225
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Zr4+:, Evans, D.A.; McGee, L.R.J. Am. Chem. Soc. 1981, 103, 2876.
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Zr4+: Evans, D.A.; McGee, L.R. Tetrahedron Lett. 1980, 21, 3975. Evans, D.A.; McGee, L.R.J. Am. Chem. Soc. 1981, 103, 2876.
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Evans, D.A.1
McGee, L.R.2
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41
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3643112892
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For threo-selective aldol reaction via tin enolates See:, Cf. ref 37d.
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For threo-selective aldol reaction via tin enolates See: Shenvi, S.; Stille, J.K. Tetrahedron Lett. 1982, 23, 627. Cf. ref 37d.
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Shenvi, S.1
Stille, J.K.2
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43
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33847086576
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Murata, S.; Suzuki, M.; Noyori, R. J. Am. Chem. Soc. 1980, 102, 3248.
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44
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84914474489
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Mulzer, J.; Brüntrup, G.; Finke, J.; Zippel, M.J. Am. Chem. Soc. 1979, 101, 7723. Yamamoto, Y.; Yatagai, H.; Naruta, Y.; Maruyama, K.J. Am. Chem. Soc. 1980, 102, 7107. Yamamoto, Y.; Maruyama, K. Tetrahedron Lett. 1980, 21, 4607. Yamamoto, Y.; Yatagai, H.; Maruyama, K.J. Chem. Soc, Chem. Commun. 1981, 162. See also: Yamamoto, Y.; Maruyama, K.J. Am. Chem. Soc. 1982, 104, 2323.
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45
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85023355637
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This result is to be compared with the corresponding reaction of the zinc enolate that gives ca. 40% of the equatorial isomers3
-
This result is to be compared with the corresponding reaction of the zinc enolate that gives ca. 40% of the equatorial isomers3
-
-
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47
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0001044174
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Lansbury, P.T.; Pattison, V.A.; Clement, W.A.; Sidler, J.D. J. Am. Chem. Soc. 1964, 86, 2247.
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