V.A. Soloshonok, T. Ono / Journal of Fluorine Chemistry 130 (2009) 547–549
549
[6] (a) K.L. Kirk, J. Fluor. Chem. 127 (2006) 1013;
(b) K.L. Kirk, J. Fluor. Chem. 72 (1995) 261.
Appendix A. Experimental Part
[7] (a) C.D. Haffner, N. Durham, A.S. Randhawa, S.M. Reister, J.M. Lenhard (Glax-
osmithklin Company), PCT Int. Appl. WO 2004/0171848 A1 (2004).
(b) J.M. Thomas, T.W. VonGeldern, Drug Dev. Res. 67 (2006) 627.
[8] D.E. Patterson, S. Xie, L.A. Jones, M.H. Osterhout, C.G. Henry, T.D. Roper, Org. Proc.
Res. Dev. 11 (2007) 624.
[9] (a) V.A. Soloshonok, H. Ueki, T.K. Ellis, Chim. Oggi/Chem. Today 26 (2008) 51;
(b) V.A. Soloshonok, H. Ueki, T.K. Ellis, Syn. Lett. (2009) 704.
[10] G. Deng, D. Ye, Y. Li, L. He, Y. Zhou, J. Wang, J. Li, H. Jiang, H. Liu, Tetrahedron 64
(2008) 10512.
General Methods Unless otherwise noted, all reagents and
solvents were obtained from commercial suppliers and used without
further purification. All of the reactions were carried out under
atmospheric conditions without any special caution to exclude air.
Unless indicated 1H and 13C NMR spectra, were taken in CDCl3
solutions at 299.95 and 75.42 MHz, respectively. Chemical shifts refer
to TMS as the internal standard.
[11] Ni(II) complex 3 was originally introduced by Professor Belokon:
(a) Y.N. Belokon, Janssen, Chim. Acta 10 (1992) 4;
(b) Y.N. Belokon, Pure Appl. Chem. 64 (1992) 1917;
(c) Y.N. Belokon, V.I. Tararov, V.I. Maleev, T.F. Saveleva, M.G. Ryzhov, Tetrahedron
Asymm. 9 (1998) 4249;
(d) Y.N. Belokon, A.G. Bulychev, S.V. Vitt, Y.T. Struchkov, A.S. Batsanov, T.V.
Timofeeva, V.A. Tsyryapkin, M.G. Ryzhov, L.A. Lysova, V.I. Bakhmutov, V.M.
Belikov, J. Am. Chem. Soc. 107 (1985) 4252.
Yields refer to isolated yields of products of greater than 95%
purity as estimated by 1H and 13C NMR spectrometry. All compounds
were characterized by 1H, and 13C NMR, high-resolution mass
spectrometry (HRMS-ESI), melting point, and optical rotation, when
applicable.
[12] For large-scale synthesis of glycine derivative 3 and its analogs, see:
(a) H. Ueki, T.K. Ellis, C.H. Martin, S.B. Bolene, T.U. Boettiger, V.A. Soloshonok, J.
Org. Chem. 68 (2003) 7104;
(b) H. Ueki, T.K. Ellis, C.H. Martin, V.A. Soloshonok, Eur. J. Org. Chem. (2003) 1954;
(c) G. Deng, J. Wang, Y. Zhou, H. Jiang, H. Liu, J. Org. Chem. 72 (2007) 8932.
[13] (a) D. Boyall, D.E. Frantz, E.M. Carreira, Org. Lett. 4 (2002) 2605;
(b) V.A. Soloshonok, H. Ohkura, A. Sorochinsky, N. Voloshin, A. Markovsky, M.
Belik, T. Yamazaki, Tetrahedron Lett. 43 (2002) 5445;
(c) A. Sorochinsky, N. Voloshin, A. Markovsky, M. Belik, N. Yasuda, H. Uekusa, T.
Ono, D.O. Berbasov, V.A. Soloshonok, J. Org. Chem. 68 (2003) 7448;
(d) V.A. Soloshonok, D.O. Berbasov, J. Fluor. Chem. 125 (2004) 1757;
(e) J.L. Moore, S.M. Taylor, V.A. Soloshonok, ARKIVOC (2005) 287;
(f) M. Yasumoto, H. Ueki, V.A. Soloshonok, J. Fluor. Chem. 128 (2007) 736.
[14] For alkyl halide alkylation, see:
Ni(II) complex of (S)-2-amino-3,3-bis-(4-fluorophenyl)propanoic
acid Schiff base with (S)-6 [(2S,20S)-5]. To a mixture of 50 g (0.1 mole)
of (S)-3, 22.0 mL (0.12 mole) of
4 in 125 mL of anhydrous
(commercial-grade) 18 g (0.16 mole) of potassium tert-butoxide
was added at ambient temperature with stirring. The reaction
progress was monitored by TLC (chloroform/acetone, 5/1). After
disappearance of starting glycine equivalent (S)-3, the reaction
mixture was poured into a beaker under stirring containing 1 L ice
water (12 mL of acetic acid). After the ice had melted the
corresponding product, was washed with water, filtered and dried
in an oven (40-45 8C) to afford the appropriate product (2S,20S)-5 in
96% chemical yields. M.p. 237–239 8C, [a]D25 +2054 (c = 0.1, MeOH);
[a]D25 +1991.9 (c = 0.49, CHCl3) [10]. 1H and 13C NMR (CDCl3) data are
similar to that reported in the literature [10].
(a) W. Qiu, V.A. Soloshonok, C. Cai, X. Tang, V.J. Hruby, Tetrahedron 56 (2000)
2577;
(b) V.A. Soloshonok, Y.N. Belokon, N.A. Kuzmina, V.I. Maleev, N.Y. Svistunova,
V.A.V.P. Solodenko, Kukhar, J. Chem. Soc., Perkin Trans. I (1992) 1525;
(c) V.P. Kukhar, Y.N. Belokon, N.Y. Svistunova, V.A. Soloshonok, A.B. Rozhenko,
N.A. Kuzmina, Synthesis (1993) 117;
(d) V.A. Basyuk, T.Y. Gromovoi, A.A. Chuiko, V.A. Soloshonok, V.P. Kukhar, Synth-
esis (1992) 449;
(S)-2-amino-3,3-bis-(4-fluorophenyl)propanoic acid, hydrochlor-
ide (1). Was prepared via disassembling of (2S,20S)-5, as previously
25
(e) X. Tang, V.A. Soloshonok, V.J. Hruby, Tetrahedron: Asymm. 11 (2000) 2917;
(f) V.A. Soloshonok, X. Tang, V.J. Hruby, L.V. Meervelt, Org. Lett. 3 (2001) 341;
(g) V.A. Soloshonok, X. Tang, V.J. Hruby, Tetrahedron 57 (2001) 6375;
(h) S.M. Taylor, T. Yamada, H. Ueki, V.A. Soloshonok, Tetrahedron Lett. 45 (2004)
9159;
described [10]. Yield 93%, m.p. 155–157 8C, [a]D +55.7 (c = 0.1,
MeOH); +55.1 [10], +56.3 [8]. 1H and 13C NMR (CD3OD) data are
(i) V.A. Soloshonok, T. Yamada, H. Ueki, A.M. Moore, T.K. Cook, K.L. Arbogast,
A.V.C.H. Soloshonok, Y. Martin, Ohfune, Tetrahedron 62 (2006) 6412;
(j) T.K. Ellis, H. Ueki, T. Yamada, Y. Ohfune, V.A. Soloshonok, J. Org. Chem. 71
(2006) 8572;
similar to that reported in the literature [8,10].
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