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8
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Thornberry, N.A.6
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13
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85030208632
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note
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We define higher α-halovinyl amino acids as α-amino acids bearing the usual α-side chain (≠H) and an additional halovinyl substituent in place of the usual α-proton.
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14
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85030207602
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note
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To our knowledge, there is only one previously reported synthesis of a higher α-halovinyl amino acid. Namely, treatment of 3,4-dimethoxy-α-ethynylphenylalanine with 47% HBr at reflux for 4 h yields internal α-bromovinyl-DOPA in 31% yield: reference 8j.
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15
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0027445840
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For other synthetic approaches to higher α-vinyl amino acids, see: (a) Colson, P.-J.; Hegedus., L. S. J. Org. Chem. 1993, 58, 5918-5924;
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(1993)
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Colson, P.-J.1
Hegedus, L.S.2
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17
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0001400822
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(c) Castelhano, A. L.; Home, S.; Taylor, G. J.; Billedeau, R.; Krantz, A. Tetrahedron, 198844, 5451-5466;
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(1988)
Tetrahedron
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Castelhano, A.L.1
Home, S.2
Taylor, G.J.3
Billedeau, R.4
Krantz, A.5
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19
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0001011296
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(e) Castelhano, A. L.; Horne, S.; Billedeau, R.; Krantz, A. Tetrahedron Lett. 1986, 27, 2435-2438;
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(1986)
Tetrahedron Lett.
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Castelhano, A.L.1
Horne, S.2
Billedeau, R.3
Krantz, A.4
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20
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84986414946
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(f) Weber, T.; Aeschimann, R.; Maetzke, T.; Seebach, D. Helv. Chim. Acta 1986, 69, 1365-1377;
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Helv. Chim. Acta
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Weber, T.1
Aeschimann, R.2
Maetzke, T.3
Seebach, D.4
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28
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0001537818
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For earlier pioneering work on related applications of PhSeX reagents, see: (a) Sharpless, K. B.; Lauer, R. F. J. Org. Chem. 1974, 39, 429-430;
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(1974)
J. Org. Chem.
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Sharpless, K.B.1
Lauer, R.F.2
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30
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0001166507
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(c) Reich, H. J.; Reich, I. L.; Renga, J. M. J. Am. Chem. Soc. 1973, 95, 5813-5815;
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Reich, H.J.1
Reich, I.L.2
Renga, J.M.3
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32
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85030206130
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note
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+ 308.1287, obsd 308.1278.
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34
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85030205675
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note
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+ 324.1236, obsd 324.1239.
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