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73
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note
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Alternatively, diol 27 could also be prepared from intermediate 19 (Scheme 19).
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There are relatively few examples of the selective oxidation of a primary alcohol in the presence of a secondary alcohol. For examples, see: (a) De Luca, L.; Giacomelli, G.; Porcheddu, A. Org. Lett. 2001, 3, 3041. (b) Einhorn, J.; Einhorn, C.; Ratajczak, F.; Pierre, J.-L. J. Org. Chem. 1996, 61, 7452. (c) Nakano, T.; Terada, T.; Ishii, Y.; Ogawa, M. Synthesis 1986, 774. (d) Tomioka, H.; Takai, K.; Oshima, K.; Nozaki, H. Tetrahedron Lett. 1981, 22, 1605. (e) Lansbury, P. T.; Hangauer, D. G.; Vacca, J. P. J. Am. Chem. Soc. 1980, 102, 3964. (f) Ketchmer, R. A.; Thompson, W. J. J. Am. Chem. Soc. 1976, 98, 3379. (g) Fried, J.; Sih, J. C. Tetrahedron Lett. 1973, 14, 3899.
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Einhorn, J.1
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78
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84988109288
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There are relatively few examples of the selective oxidation of a primary alcohol in the presence of a secondary alcohol. For examples, see: (a) De Luca, L.; Giacomelli, G.; Porcheddu, A. Org. Lett. 2001, 3, 3041. (b) Einhorn, J.; Einhorn, C.; Ratajczak, F.; Pierre, J.-L. J. Org. Chem. 1996, 61, 7452. (c) Nakano, T.; Terada, T.; Ishii, Y.; Ogawa, M. Synthesis 1986, 774. (d) Tomioka, H.; Takai, K.; Oshima, K.; Nozaki, H. Tetrahedron Lett. 1981, 22, 1605. (e) Lansbury, P. T.; Hangauer, D. G.; Vacca, J. P. J. Am. Chem. Soc. 1980, 102, 3964. (f) Ketchmer, R. A.; Thompson, W. J. J. Am. Chem. Soc. 1976, 98, 3379. (g) Fried, J.; Sih, J. C. Tetrahedron Lett. 1973, 14, 3899.
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Nakano, T.1
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0001495283
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There are relatively few examples of the selective oxidation of a primary alcohol in the presence of a secondary alcohol. For examples, see: (a) De Luca, L.; Giacomelli, G.; Porcheddu, A. Org. Lett. 2001, 3, 3041. (b) Einhorn, J.; Einhorn, C.; Ratajczak, F.; Pierre, J.-L. J. Org. Chem. 1996, 61, 7452. (c) Nakano, T.; Terada, T.; Ishii, Y.; Ogawa, M. Synthesis 1986, 774. (d) Tomioka, H.; Takai, K.; Oshima, K.; Nozaki, H. Tetrahedron Lett. 1981, 22, 1605. (e) Lansbury, P. T.; Hangauer, D. G.; Vacca, J. P. J. Am. Chem. Soc. 1980, 102, 3964. (f) Ketchmer, R. A.; Thompson, W. J. J. Am. Chem. Soc. 1976, 98, 3379. (g) Fried, J.; Sih, J. C. Tetrahedron Lett. 1973, 14, 3899.
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Tomioka, H.1
Takai, K.2
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Nozaki, H.4
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0001602420
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There are relatively few examples of the selective oxidation of a primary alcohol in the presence of a secondary alcohol. For examples, see: (a) De Luca, L.; Giacomelli, G.; Porcheddu, A. Org. Lett. 2001, 3, 3041. (b) Einhorn, J.; Einhorn, C.; Ratajczak, F.; Pierre, J.-L. J. Org. Chem. 1996, 61, 7452. (c) Nakano, T.; Terada, T.; Ishii, Y.; Ogawa, M. Synthesis 1986, 774. (d) Tomioka, H.; Takai, K.; Oshima, K.; Nozaki, H. Tetrahedron Lett. 1981, 22, 1605. (e) Lansbury, P. T.; Hangauer, D. G.; Vacca, J. P. J. Am. Chem. Soc. 1980, 102, 3964. (f) Ketchmer, R. A.; Thompson, W. J. J. Am. Chem. Soc. 1976, 98, 3379. (g) Fried, J.; Sih, J. C. Tetrahedron Lett. 1973, 14, 3899.
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Lansbury, P.T.1
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Vacca, J.P.3
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There are relatively few examples of the selective oxidation of a primary alcohol in the presence of a secondary alcohol. For examples, see: (a) De Luca, L.; Giacomelli, G.; Porcheddu, A. Org. Lett. 2001, 3, 3041. (b) Einhorn, J.; Einhorn, C.; Ratajczak, F.; Pierre, J.-L. J. Org. Chem. 1996, 61, 7452. (c) Nakano, T.; Terada, T.; Ishii, Y.; Ogawa, M. Synthesis 1986, 774. (d) Tomioka, H.; Takai, K.; Oshima, K.; Nozaki, H. Tetrahedron Lett. 1981, 22, 1605. (e) Lansbury, P. T.; Hangauer, D. G.; Vacca, J. P. J. Am. Chem. Soc. 1980, 102, 3964. (f) Ketchmer, R. A.; Thompson, W. J. J. Am. Chem. Soc. 1976, 98, 3379. (g) Fried, J.; Sih, J. C. Tetrahedron Lett. 1973, 14, 3899.
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Ketchmer, R.A.1
Thompson, W.J.2
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Fried, J.1
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85088719325
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note
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2 allylic oxidation in approximately 4% yield. This material could be recycled by stirring in 2-propanol and PPTS, forming 38 in modest yield.
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1H NMR.
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90
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0026593160
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