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24
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0348143469
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For recent use of this versatile chiral building block, see: (a) Dondoni, A.; Massi, A.; Minghini, E.; Sabbatini, S.; Bertolasi, V. J. Org. Chem. 2003, 68, 6172-6183. (b) Catalano, J. G.; Deaton, D. N.; Furfine, E. S.; Hassell, A. M.; McFayden, R. B.; Miller, A. B.; Miller, L. R.; Shewchuk, L. M.; Willard, D. H.; Whright, L. L. Bioorg. Med. Chem. Lett. 2004, 14, 275-278. (c) Dondoni, A.; Catozzi, N.; Marra, A. J. Org. Chem. 2004, 69, 5023-5036. (d) Dondoni, A.; Giovanni, P. P.; Massi, A. Org. Lett. 2004, 6, 2929-2932.
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25
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3543008950
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For recent use of this versatile chiral building block, see: (a) Dondoni, A.; Massi, A.; Minghini, E.; Sabbatini, S.; Bertolasi, V. J. Org. Chem. 2003, 68, 6172-6183. (b) Catalano, J. G.; Deaton, D. N.; Furfine, E. S.; Hassell, A. M.; McFayden, R. B.; Miller, A. B.; Miller, L. R.; Shewchuk, L. M.; Willard, D. H.; Whright, L. L. Bioorg. Med. Chem. Lett. 2004, 14, 275-278. (c) Dondoni, A.; Catozzi, N.; Marra, A. J. Org. Chem. 2004, 69, 5023-5036. (d) Dondoni, A.; Giovanni, P. P.; Massi, A. Org. Lett. 2004, 6, 2929-2932.
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4444268846
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For recent use of this versatile chiral building block, see: (a) Dondoni, A.; Massi, A.; Minghini, E.; Sabbatini, S.; Bertolasi, V. J. Org. Chem. 2003, 68, 6172-6183. (b) Catalano, J. G.; Deaton, D. N.; Furfine, E. S.; Hassell, A. M.; McFayden, R. B.; Miller, A. B.; Miller, L. R.; Shewchuk, L. M.; Willard, D. H.; Whright, L. L. Bioorg. Med. Chem. Lett. 2004, 14, 275-278. (c) Dondoni, A.; Catozzi, N.; Marra, A. J. Org. Chem. 2004, 69, 5023-5036. (d) Dondoni, A.; Giovanni, P. P.; Massi, A. Org. Lett. 2004, 6, 2929-2932.
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17444383697
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note
-
An analogous Henry reaction-based strategy for the synthesis of 4-hydroxyornithine was previously reported by Rudolph et al. (ref 9). This approach, however, suffers both from an unfavorable stereoselectivity and from a very low yield in the key nitroaldol reaction step and therefore was not pursued further.
-
-
-
-
28
-
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17444384046
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see Supporting Information
-
Although N-Boc-protected (5)-2-amino-1,4-butandiol 7 is commercially available (Aldrich), its relatively high price leads us to recommend its preparation on a multigram scale from inexpensive L-aspartic acid (see Supporting Information).
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-
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29
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84908806186
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For an alternative approach to 6 starting from N-tert-butonycarbonyl-L- aspartic acid γ-benzyl ester, see: Ouerfelli, O.; Ishida, M.; Shinozaki, H.; Nakanishi, K.; Ohfune, Y. Synlett 1993, 409-410.
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note
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Ab initio MO calculations (DFTYB3LYP/6-311G+) showed an energy difference of about 7.8 kcal/mol between 9 and the six-membered cyclic N,O-acetal 10, indicating that only traces of this regioisomer are to be expected.
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33
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17444411390
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note
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2, rt, 36 h) according to ref 15.
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37
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17444364357
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note
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Low stereoselectivity in nitroaldol reactions with aldehydes bearing a stereogenic center at the β-position has been observed previously. See ref 9 and references therein.
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17444402740
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note
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Since β-nitro alcohols 12 and 13 were difficult to separate, 12 was used as a mixture of diastereomers (97:3). The minor diastereomer could be easily removed by flash chromatography on silica gel at the stage of the N°-Z-protected β-amino alcohol 17.
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