1
408
Popkov et al.:
6
7
7
.79, H18 5.91, H19 4.42 3Ja = 7.7 3Jb = 5.0, H21 3.45 H21 4.31 2Ja = 12.7, H23 8.00, H24
a
b
3
3
3
3
.28, H25 7.12, H26 7.28, H27 8.00, H28a 3.82 Ja = 14.1 Jb = 5.0, H28b 4.05 J = 14.1 Jb
=
a
1
3
.7, H30 7.38, H31 7.76, H32 7.35, H34 7.76, H35 7.35, H36 7.19, H37 7.55. C NMR
(
125 MHz, CDCl ): C1 57.02, C2 23.63, C3 30.77, C4 70.44, C5 180.06, C7 123.18, C8
3
1
1
1
1
1
32.24, C9 120.47, C10 133.57, C11 126.11, C12 170.78, C13 134.50, C14 127.25, C15
a
28.40, C16 129.06 , C17 128.35, C18 127.49, C19 71.33, C20 178.58, C21 63.01, C22
a
33.16, C23 131.39, C24 128.76, C25 128.74 , C26 128.76, C27 131.39, C28 39.87, C29
b
c
b
c
32.55, C30 126.20, C31 128.26 , C32 125.45 , C33 131.85, C34 128.15 , C35 128.74 , C36
a, b,
c
25.75, C37 123.40, C38 133.11 (
Note: Som e assign m en ts of n aph th alen e rin g carbon s in 13C NMR spectrum of 3 h ave a
– assign m en t can be in terch an ged).
sm aller con fiden ce, because experim en ts were m ade in in version m ode an d resolution in F1
axis was n ot so good from poin t of view of very crowded spectrum area belon gin g to th e
n aph th alen e carbon s an d proton s (even in 125 an d 500 MHz spectra, respectively). For
C38H33N NiO (637.2) calculated: 71.49% C, 5.21% H, 6.58% N; foun d: 71.68% C, 5.22% H,
3
3
6
.52% N.
(
S)-2-Am in o-3-(1-n aph th yl)propan oic Acid 1
A m ixture of 3 (9.5 g, 15 m m ol), 50 m l MeOH an d 6 M HCl was refluxed for 1 h an d th en
evaporated to dryn ess. Water (50 m l) was added to th e residue an d th e in soluble m aterial
(
(
correspon din g to BPB·HCl) was filtered off, wash ed with water (4 × 50 m l), dried an d stored
sim ilar to ref.15). Un der stirrin g, pH of th e water solution was adjusted to 9–10 with aque-
ous NH , th e precipitate of 1 was filtered off, wash ed with ch loroform (40 m l), water (100 m l),
3
cold MeOH (40 m l), an d dried.
2
D
1
27
Am in o acid 1: Yield (73% based on 3), m .p. 229–231 °C. [α ] –15.0 (c 1, 0.3 M HCl), ref.
2
0
1
3
3
[
α ] –15.0 (c 0.97, 0.3 M HCl). H NMR (500 MHz, CDCl ): H19 4.56 Ja = 9.2 Jb = 5.9, H28a
D
3
3
.64 3Ja = 14.8 Jb = 5.9, H28b 4.05 Ja = 14.8 Jb = 9.2, H30 7.58, H31 7.63, H32 8.06, H34
3
3
3
1
3
8
.12, H35 7.73, H36 7.78, H37 8.22. C NMR (125 MHz, CDCl ): C19 56.05, C20 174.11,
3
1
6
knowledged.
REFERENCES AND NOTES
1
2
. a) Ma J. A.: Angew. Chem., Int. Ed. 2003, 42, 4290; b) Maruoka K., Takashi O.: Chem. Rev.
003, 103, 3013.
2
. a) Schöllkopf U.: Tetrahedron 1983, 39, 2085; b) Bull S. D., Davies S. G., Epstein S. W.,
Leech M. A., Ouzman J. V. A.: J. Chem. Soc., Perkin Trans. 1 1998, 2321; c) Evans D. A.,
Bartroli H., Shih T. L.: J. Am. Chem. Soc. 1981, 103, 2127; d) Evans D. A., Weber A. E.:
J. Am. Chem. Soc. 1986, 108, 6757; e) Seebach D., Sting A. R., Hoffmann M.: Angew.
Chem., Int. Ed. Engl. 1996, 35, 2708; f) Hintermann T., Seebach D.: Helv. Chim. Acta
1
998, 81, 2093; g) Seebach D., Hoffmann M.: Eur. J. Org. Chem. 1998, 1137; h) Oppolzer W.,
Collect. Czech. Chem. Commun. (Vol. 70) (2005)