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85038536449
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note
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1H NMR data are shown in experimental section. (formula presented)
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31
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0000733873
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b) Beaulieu, P. L.; Duceppe, J.-S.; Johnson, C J. Org. Chem. 1991, 56, 4196.
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0141712450
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8. 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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Zhang, X.-L.11
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33
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85038533344
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note
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9. The dihydroxylation using the bulky DHQ or DHQD ligated osmium reagent was very sluggish. Most of (Z)-3 was almost recovered along with a small amount of phenyl ketone compounds, which would be oxydized products of diols 9 and 10.
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34
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0000894454
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10. a) Cha, J. K.; Christ, W. J.; Kishi, Y. Tetrahedron Lett. 1983, 24, 3943.
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Cha, J.K.1
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33748610978
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b) Christ, W. J.; Cha, J. K.; Kishi, Y. Tetrahedron Lett. 1983, 24, 3947.
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Christ, W.J.1
Cha, J.K.2
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11. a) Kolb, H. C.; VanNieuwenhze, M. S.; Sharpless, K. B. Chem. Rev. 1994, 94, 2483.
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Kolb, H.C.1
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Sharpless, K.B.3
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37
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11944249437
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4 and the allylic substituent, in which the acidity of the latter was a crucial factor. Accordingly, the acidic NH proton of the allylic NHBoc group of (Z)-5 and (Z)-6 might affect the selectivity so as to make syn attack of the reagent prefered. b) Cha, J. K.; Kim, N.-S. Chem. Rev. 1995, 95, 1761.
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Cha, J.K.1
Kim, N.-S.2
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0028210293
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12. In general, it is known to be difficult to achieve stereoselective dihydroxylation of (Z)-olefins using AD-mix reagents. The high selectivities attained here might be explained by the effect of hydrogen bonding between homoallyl alcohol moiety of the deprotected (Z)-olefins and oxo group on osmium as suggested by Sharpless: see, VanNieuwenhze, M. S.; Sharpless, K. B. Tetrahedron Lett. 1994, 35, 843.
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VanNieuwenhze, M.S.1
Sharpless, K.B.2
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39
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85038534121
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note
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13. The X-ray crystallographic data of the compound 13c have been deposited to Cambridge Crystallographic Data Center.
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40
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85038531201
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note
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5h of the optical rotation of the compound 17 has ever been made, but the reason for the large difference between the value of the optical rotation obtained by us and the reference's one is not clear.
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