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(b) A similar regioselectivity was also described with unprotected acids: Churn, N. J.; Young, D. W. Tetrahedron Lett. 1995, 36, 151-154.
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33746915346
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note
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1H NMR data and the RP-HPLC traces suggested equally high conversions/ yields in all six cases.
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For previous examples of intramolecular Fukuyama-Mitsunobu reactions on solid phase, see: (a) Kung, P. P.; Swayze, E. Tetrahedron Lett. 1999, 40, 6551-5654.
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1442360074
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Previously employed in polyamine synthesis on solid phase: (a) Olsen, C. A.; Witt, M.; Jaroszewski, J. W.; Franzyk, H. Synlett 2004, 473-476.
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33746911810
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note
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3P, 40%.
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27
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0001758406
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For representative examples, see: (a) Nefzi, A.; Ostresh, J. M.; Giulianotti, M. A.; Houghten, R. A. J. Comb. Chem. 1999. 1, 195-198.
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note
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R (A-3) = 14.4 min.
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34
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33746872788
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note
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D +45.2° (c 1.4, MeOH).
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35
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33746876204
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note
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2 and MeOH) were pooled, and the solvents were removed in vacuo. The crude material was dissolved in MeCN (1 mL) and purified by preparative RP-HPLC (17 mg, 33%).
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36
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27644470502
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For a comprehensive review of previously available methods for formation of the amino functionality of solid phase, see: Olsen, C. A.; Franzyk, H.; Jaroszewski, J. W. Synthesis 2005, 2631-2653.
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0034684250
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For examples of DOS based on privileged structures/scaffolds, see: (a) Nicolaou, K. C.; Pfefferkorn, J. A.; Roecker, A. J.; Cao, G.-Q.; Barluenga, S.; Mitchell, H. J. J. Am. Chem. Soc. 2000, 122, 9939-9953.
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(b) Nicolaou, K. C.; Pfefferkorn, J. A.; Mitchell, H. J.; Roecker, A. J.; Barluenga, S.; Cao, G.-Q.; Affleck, R. L.; Lillig, J. E. J. Am. Chem. Soc. 2000, 122, 9954-9967.
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For recent examples of aziridination in solution, see: Kim, S. K.; Jacobsen, E. N. Angew. Chem., Int. Ed. 2004, 43, 3952-3954, and references therein.
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