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0030971776
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King, G. R.; Mander, L. N.; Monck, N. J. T.; Morris, J. C.; Zhang, H. J. Am. Chem. Soc. 1997, 119, 3828-3829.
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King, G.R.1
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Monck, N.J.T.3
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Zhang, H.5
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3
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0001387037
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Washington, D.C.
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Mander, L. N. Chem. Rev. (Washington, D.C.) 1992, 92, 573.
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(a) Sharpless, K. B.; Amberg, W.; Bennani, Y. L.; Crispino, G. A.; Hartung, J.; Jeong, K.-S.; Kwong, H.-L.; Morikawa, K.; Wang, Z.-M.; Xu, D.; Zhang, X.-L. J. Org. Chem. 1992, 57, 2768.
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Sharpless, K.B.1
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Hartung, J.5
Jeong, K.-S.6
Kwong, H.-L.7
Morikawa, K.8
Wang, Z.-M.9
Xu, D.10
Zhang, X.-L.11
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5
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0000067960
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Catalytic Asymmetric Dihydroxylation
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Ojima, I., Ed.; VCH: Weinheim, Germany
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(b) Johnson, R. A.; Sharpless, K. B. Catalytic Asymmetric Dihydroxylation, In Catalytic Asymmetric Synthesis; Ojima, I., Ed.; VCH: Weinheim, Germany, 1993; pp 227-272.
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(1993)
Catalytic Asymmetric Synthesis
, pp. 227-272
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Johnson, R.A.1
Sharpless, K.B.2
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9
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84892597425
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(d) Monododoev, G. T.; Przhiyalpovskay, N. M.; Belov, V. N.; J. Org. Chem. USSR. 1965, 1, 1257.
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11
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0001573935
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Murthy, A. R.; Sundar, N. S.; Subba Rao, G. S. R. Tetrahedron 1982, 38, 2831.
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Tetrahedron
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Murthy, A.R.1
Sundar, N.S.2
Subba Rao, G.S.R.3
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12
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84892617472
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note
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8e,9 A more efficient synthesis was achieved starting from 1,7-dimethoxynaphthalene, and the details are presented in the Supporting Information.
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16
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85007947149
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(d) Horii, Z.; Matsumoto, Y.; Momose, T. Chem. Pharm. Bull. 1971, 19, 1245.
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Horii, Z.1
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20
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0010291446
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Trost, B. M., Fleming, I., Eds.; Pergamon Press: and references therein
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Mander, L. N. in Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: 1991; Vol 8, pp 489-522 and references therein.
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(1991)
Comprehensive Organic Synthesis
, vol.8
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Mander, L.N.1
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21
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0000204956
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Hook, J. M.; Mander, L. N.; Woolias, M. Tetrahedron Lett. 1982, 23, 1095.
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Tetrahedron Lett.
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Hook, J.M.1
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Woolias, M.3
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22
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84892583102
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note
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5a-c to be the more stable of the two isomers, so given time, the equilibrium will favor the thermodynamically more stable product.
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23
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84892599179
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Available from Aldrich Chemical Co.
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Available from Aldrich Chemical Co.
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25
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84892600178
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note
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For comparative purposes, the racemate was obtained by carrying out the identical reaction, in the absence of ligand, to afford (±)-8 in 89% yield. This reaction was appreciably slower, taking 18 h at room temperature.
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26
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84892616126
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note
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17a-c was employed; details are provided in the Supporting Information. When the Kakisawa procedure was followed to completion, the absolute configuration at C3 was determined to be S. As the dihydroxylation is stereospecific, this means that the absolute stereochemistry at C2 must be R. As expected, the absolute configuration matches that predicted by the Sharpless stereoselectivity rules.
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28
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33947086629
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(b) Sullivan, G. R.; Dale, J. A.; Mosher, H. S. J. Org. Chem. 1973, 38, 2143.
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Sullivan, G.R.1
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2142858450
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(d) Ohtani, I.; Kusumi, T.; Kashman, Y.; Kakisawa, H. J. Am. Chem. Soc. 1991, 113, 4092.
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0005519280
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Kolb, H. C.; Andersson, P. G.; Sharpless, K. B. J. Am. Chem. Soc. 1994, 116, 1278.
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Kolb, H.C.1
Andersson, P.G.2
Sharpless, K.B.3
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84892586253
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Ohta, S.; Shimabayashi, A.; Aono, M.; Okamoto, M. Synthesis, 1982, 837.
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Synthesis
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Ohta, S.1
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35
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0028272256
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(a) Buisson, D.; Cecchi, R.; Laffitte, J.-A.; Guzzi, U.; Azerad, R. Tetrahedron Lett. 1994, 35, 3091.
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Buisson, D.1
Cecchi, R.2
Laffitte, J.-A.3
Guzzi, U.4
Azerad, R.5
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0028318614
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(b) Genêt, J. P.; Pfister, X.; Ratovelomanana-Vidal, V.; Pinel, C.; Laffitte, J. A. Tetrahedron Lett. 1994, 35, 4559.
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Genêt, J.P.1
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Pinel, C.4
Laffitte, J.A.5
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37
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0000086893
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For general directions see
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For general directions see Furber, M.; Mander, L. N.; Patrick, G. L. J. Org. Chem. 1990, 55, 4860.
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(1990)
J. Org. Chem.
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Furber, M.1
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Patrick, G.L.3
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