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18
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0347613737
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note
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Based on the HPLC analysis, there was no racemization in the epoxide-opening process; see the Supporting Information for details.
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19
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33845554880
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Red-Al was used for the transformation of allylic alcohol epoxides to 1,3-diols, see: a) P. Ma, V. S. Martin, S. Masamune, K. B. Sharpless, S. M. Viti, J. Org. Chem. 1982, 47, 1378-1380;
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Ma, P.1
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0345491105
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24
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0038732511
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The role of counterions in the regioselective opening of 2,3-epoxy alcohol was studied theoretically, see: I. Infante, C. Bonini, F. Leij, G. Righi, J. Org. Chem. 2003, 68, 3773-3780. These results also support our hypothesis.
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Infante, I.1
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25
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0348243530
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note
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See the Supporting Information for details.
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26
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0348243531
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note
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The absolute configuration of 11a was determined to be 2R, 3S. See the Supporting Information for details.
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27
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0000963705
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M. Oshima, H. Yamazaki, I. Shimizu, M. Nisar, J. Tsuji, J. Am. Chem. Soc. 1989, 111, 6280-6287.
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28
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0023860773
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There are marked differences between the two major metabolites (R)- and (S)-norfluoxetine in regard to their inhibition of 5-HT reuptake, see: a) D. W. Robertson, N. D. Jones, J. K. Swartzendruber, K. S. Yang, D. T. Wong, J. Med. Chem. 1988, 31, 185-189,
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For representative examples of the synthesis of (R)-17, see: a) M. Srebnik, P. V. Ramachandran, H. C. Brown, J. Org. Chem. 1988, 53, 2916-2920;
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Senanayake, C.H.7
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36
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0342601552
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After the epoxide-opening reaction, [15]crown-5 was recovered in 87% yield. See the Supporting Information. Alternatively, immobilized crown ethers can be applied to this reaction. For an example of the immobilization of crown ethers, see: A. Favre-Réguillon, N. Dumont, B. Dunjic, M. Lemaire, Tetrahedron Lett. 1997, 38, 1343-1360.
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Favre-Réguillon, A.1
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Lemaire, M.4
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