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9
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0016607472
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β-Hydroxyaspartic acids are present in many microorganisms
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For example, derivatives of β-hydroxyaspartic acid are known inhibitors of L-asparagine synthetase: (a) Mokotoff, M.; Bagaglio, J. F.; Parikh, B. S. J. Med. Chem. 1975, 18, 354-358. β-Hydroxyaspartic acids are present in many microorganisms:
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Mokotoff, M.1
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0016774502
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Various syntheses of L-erythro-β-hydroxyaspartic acid, a constituent of several proteins involved in the blood clotting cascade, have been reported
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(c) Ishiyama, T.; Furuta, T.; Takai, M.; Okimoto, Y.; Aizawa, S.; Shiman, A.; Yonehara, H. J. Antibiot. 1975, 28, 821-823. Various syntheses of L-erythro-β-hydroxyaspartic acid, a constituent of several proteins involved in the blood clotting cascade, have been reported:
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Ishiyama, T.1
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Aizawa, S.5
Shiman, A.6
Yonehara, H.7
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14
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0025082151
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Derivatives of β-alkoxy and hydroxy aspartates are known nontransportable glutamate transporter blockers
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(f) Wagner, R.; Tilley, J. W.; Lovey, K. Synthesis 1990, 785-786. Derivatives of β-alkoxy and hydroxy aspartates are known nontransportable glutamate transporter blockers:
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Synthesis
, pp. 785-786
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Wagner, R.1
Tilley, J.W.2
Lovey, K.3
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15
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0034613643
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(g) Shimamoto, K.; Shigeri, Y.; Yasuda-Kamatani, Y.; Lebrun, B.; Yumoto, N.; Nakajima, T. Bioorg. Med. Chem. Lett. 2000, 10, 2407-2410.
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Yumoto, N.5
Nakajima, T.6
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For a summary of recent asymmetric catalysis using nucleophiles, see: Dalko, P. I.; Moisan, L. Angew. Chem., Int. Ed. 2001, 40, 3726-3748.
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Dalko, P.I.1
Moisan, L.2
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17
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0003515364
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Lactone synthesis from ketenes
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For other, excellent uses of cinchona alkaloids in asymmetric synthesis see the following. Ester synthesis from ketenes: (a) Samtleben, R.; Pracejus, H. J. Prakt. Chem. 1972, 314, 157-169. Lactone synthesis from ketenes:
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Samtleben, R.1
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0001547021
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Baylis-Hillman reaction
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(c) Calter, M. A. J. Org. Chem. 1996, 61, 8006-8007. Baylis-Hillman reaction:
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Calter, M.A.1
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Osmylation reactions
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(d) Iwabuchi, Y.; Nakatani, M.; Yokoyama, N.; Hatakeyama, S. J. Am. Chem. Soc. 1999, 121, 10219-10220. Osmylation reactions:
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Iwabuchi, Y.1
Nakatani, M.2
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Hatakeyama, S.4
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21
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Phase-transfer catalysis
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(e) Kolb, H. C.; VanNieuwenzhe, M. S.; Sharpless, K. B. Chem Rev. 1994, 94, 2483-2547. Phase-transfer catalysis:
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33845185214
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(g) O'Donnell, M. J.; Bennett, W. D.; Wu, S. J. Am. Chem. Soc. 1989, 111, 2353-2355. Kacprzak, K.; Gawronski, J. Synthesis-Stuttgart 2001, 7, 961-998.
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33845185214
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(g) O'Donnell, M. J.; Bennett, W. D.; Wu, S. J. Am. Chem. Soc. 1989, 111, 2353-2355. Kacprzak, K.; Gawronski, J. Synthesis-Stuttgart 2001, 7, 961-998.
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25
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0043136964
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note
-
α-Chloroamine 5 is easily made by the condensation of benzamide with ethyl glyoxylate followed by reaction with oxalyl chloride. See Supporting Information.
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27
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0032573890
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Horstmann, T.E.1
Guerin, D.J.2
Miller, S.J.3
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34
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0035823834
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We have recently reported a catalytic, asymmetric synthesis of β-lactams: (a) Hafez, A. M.; Taggi, A. E.; Dudding, T.; Lectka, T. J. Am. Chem Soc. 2001, 123, 10853-10859.
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(b) Hafez, A. M.; Taggi, A. E.; Wack, H.; Drury, W. J., III; Lectka, T. Org. Lett. 2000, 2, 3963-3965.
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0034674972
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(c) Taggi, A. E.; Hafez, A. M.; Wack, H.; Young, B.; Drury, W. J., III; Lectka, T. J. Am. Chem. Soc. 2000, 122, 7831-7832.
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0000712093
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We have used powered carbonates as effective nonnucleophilic, stoichiometric bases for ketene generation: Hafez, A. M.; Taggi, A. E.; Wack, H.; Esterbrook, J.; Lectka, T. Org. Lett. 2001, 3, 2049-2051.
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Hafez, A.M.1
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Lectka, T.5
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40
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0029877120
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The ring opening of β-lactams is known to be catalyzed by nucleophiles including azides: Palomo, C.; Aizpurua, J. M.; Galarza, R.; Mielgo, A. J. Chem. Soc., Chem. Commun. 1996, 633-634.
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Mielgo, A.4
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41
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0043136963
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note
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Epimerization of the hydroxymethyl group in 9h was not observed under the reaction conditions.
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