3018
X. Yuan et al. / Tetrahedron: Asymmetry 12 (2001) 3015–3018
The filtrate left after separation of the complex was
evaporated, leaving a pale yellow solid of enriched
(R)-1, which was racemized with a 25 wt% aqueous
NaOH solution for recycling, to afford a white solid
(5.10 g, 99.0 wt%, 110.2% recovery). Mp 154–155°C;
[h]2D3=0 (c 1, C2H5OH).
1996, 35, 72–74; (c) Takeuchi, M.; Yoda, S.; Imada, T.;
Shinkai, S. Tetrahedron 1997, 53, 8335–8348; (d) Toda, F.
Acc. Chem. Res. 1995, 28, 480–486; (e) Davies, I. W.;
Reider, P. J. Chem. Ind. 1996, 412–415; (f) Kaupp, G.
Angew. Chem., Int. Ed. Engl. 1994, 33, 728–729; (g)
Bortolini, O.; Fantin, G.; Fogagnolo, M.; Medici, A.;
Pedrini, P. J. Chem. Soc., Chem. Commun. 2000, 365–366.
9. Toda, F.; Tanaka, K.; Stein, Z.; Golderg, I. J. Org.
Chem. 1994, 59, 5748–5751.
10. The inclusion complex (S)-(+)-1/
Acknowledgements
1
D
-(−)-2b: H NMR (500
MHz, methanol-d4), l: 0.914 (3H, t, J=12.5 Hz), 1.330
(12H, m), 1.507 (3H, d, 12.5 Hz), 1.618 (2H, t), 2.875
(2H, m), 3.072 (2H, m), 3.641–3.751 (4H, m), 3.899 (3H,
s), 4.019 (1H, q, J=12.5 Hz), 7.070–7.715 (6H, m) ppm;
elemental analysis, calcd for C28H45NO8: C, 64.17; N,
2.67; H, 8.59; found: C, 64.52; N, 2.42; H, 8.35%.
We gratefully acknowledge supports from the Major
State Basic Research Development Program (No.
G200077500), the National Natural Science Founda-
tion of China (90101028) and the Key Project under
Science and Technology Ministry of China (No. 96-
902-03-04).
11. IR (KBr) of (S)-(+)-1/D-(−)-2b, wmax: 3403 (br), 3243 (br),
3057, 2952 (s), 2854, 2450, 1637, 1608, 1560 (s), 1505,
1488 (br), 1396, 1338, 1290, 1259, 1214, 1162, 1135, 1111,
1026, 895, 856, 817 cm−1
.
References
12. Crystal data for 1:1 inclusion complex of (S)-(+)-1 and
-(−)-2b: C28H45NO8; colorless lamellar crystal (0.4×
0.25×0.01 mm); Mr=523.62; triclinic; space group P1
D
1. Chan, A. S. C. Chemtech. 1993, 3, 46–51.
2. (a) Peter, J. H.; Eric, L. Org. Process Res. Dev. 1997, 1,
72–76; (b) Davis, M. E.; Wan, K. T. WO 95/22405; (c)
Lopez, F. J.; Ferrine, S. A.; Reyes, M. S.; Roman, R.
Tetrahedron: Asymmetry 1997, 8, 2497–2500; (d) Zhang,
X. WO 99/59721.
,
(no. 1), a=6.1246(3), b=8.7821(4), c=27.1377 (11) A,
h=92.707(1),
i=95.925(1),
k=90.101(1)°;
V=
1450.20(11) A ; Z=2; zcalcd=1.167 g cm−3, F (0 0 0)=
552; v(MoKa)=0.085 mm−1; Bruker SMART CCD
diffractometer; graphite-monochromated MoKa (u=
3
,
3. (a) Giordano, C.; Castaldi, G.; Casagrande, F.; Belli, A.
J. Chem. Soc., Perkin Trans. 1 1982, 2575–2581; (b)
Giordiano, C.; Villa, M.; Annunziata, R. Synth. Com-
mun. 1990, 20, 383–392; (c) Santo, R. D.; Costi, R.;
Massa, S.; Artico, M. Synth. Commun. 1995, 25, 787–793.
4. (a) Crosby, J. Tetrahedron 1991, 47, 4789–4846; (b) Paul,
V. E.; Francis, X. M. C.; Jorge, L. WO 96/36584; (c)
Holton, P. G. DE 3025448 (1981); (d) Oak, G. M.;
Chodankar, N. K. EP 1029846 (2000); (e) Yadav, N. K.;
Kulkarni, B. D.; Khomane, R. B. US 6093830 (2000).
5. Manimaran, T.; Impastato, F. J. US 5015764 (1991).
6. Arai, K. J. Syn. Org. Chem. Jpn. 1986, 44, 486–489.
7. Patil, D. R.; Ramachandran, V. WO 96/22959.
8. (a) Deng, J.; Chi, Y.; Fu, F.; Yu, K.; Zhu, J.; Jiang, Y.
Tetrahedron: Asymmetry 2000, 11, 1729–1732; (b) Araki,
K.; Inada, K.; Shinkai, S. Angew. Chem., Int. Ed. Engl.
,
0.71073 A) radiation; T=295(2) K; 2q range, 1.52–
55.00°; total reflection collected 16658, in which 10163
unique reflection collected (Rint=0.0418); empirical
adsorption corrections; data processing was accomplished
with SAINT processing program. The structure was
solved by direct methods and refined by full-matrix least-
squares on F2 using SHELX-97, including the positional
and anisotropic thermal parameters of the nonhydrogen
atoms. Hydrogen atoms were generated in idealized posi-
tions attached to the named C, N, O atoms and refined in
riding model. The refinement calculations converged at
R=0.0590, wR2=0.1112.
13. Condition of HPLC: Chirex Phase 2005 (250×4.3 mm,
Phenomenex Inc.) as chiral column, and 0.05 M ammo-
nium acetate in methanol as an eluent.