Enantioselective Reactions of a Lithiated a-Thioallyl Carbanion
FULL PAPERS
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X-ray Crystallographic Study
X-ray crystal structure analysis for (R)-23b: formula
C18H25NO2S, M=319.45, colorless crystal 0.35×0.25×
0.10 mm, a=6.010(1), b=7.349(1), c=39.431(1) Å, V=
1741.6(4) Å3, 1calc =1.218 gcmÀ3, m=1.696 mmÀ1, empirical
absorption correction (0.588 ꢀ T ꢀ 0.849), Z=4, ortho-
rhombic, space group P212121 (No. 19), l=1.54178 Å, T=
223 K, w and f scans, 5706 reflections collected (Æh, Æk, Æ
l), [(sinq)/l]=0.60 ÅÀ1, 2856 independent (Rint =0.032) and
2816 observed reflections [I ꢁ 2s(I)], 204 refined parame-
ters, R=0.032, wR2 =0.081, Flack parameter 0.07(2), max.
residual electron density 0.20 (À0.19) eÅÀ3, hydrogen atoms
calculated and refined as riding atoms.
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X-ray crystal structure analysis for rac-10: formula
C20H31NO2SSi, M=377.61, colorless crystal 0.40×0.20×
0.20 mm, a=10.063(1), b=10.716(1), c=11.783(1) Å, a=
3
˚
77.20(1), b=67.68(1), g=66.76(1), V=1076.2(2) Å , 1calc
=
1.165 gcmÀ3, m=1.959 mmÀ1, empirical absorption correction
¯
(0.508 ꢀ T ꢀ 0.695), Z=2, triclinic, space group P1
A
l=1.54178 Å, T=223 K, w and f scans, 10260 reflections
collected (Æh, Æk, Æl), [(sinq)/l]=0.60 ÅÀ1, 3675 inde-
pendent (Rint =0.029) and 3587 observed reflections [I ꢁ 2
s(I)], 233 refined parameters, R=0.036, wR2 =0.097, max.
residual electron density 0.30 (À0.24) eÅÀ3, hydrogen atoms
calculated and refined as riding atoms.
Data sets were collected with a Nonius KappaCCD dif-
fractometer. Programs used: data collection COLLECT,[14]
data reduction Denzo-SMN,[15] absorption correction
Denzo,[16] structure solution SHELXS-97,[17] structure refine-
ment SHELXL-97,[18] graphics SCHAKAL.[19]
Crystallographic data (excluding structure factors) for the
structures reported in this paper have been deposited with
the Cambridge Crystallographic Data Centre as supplemen-
tary publication no. CCDC-603269 and CCDC-603270.
Copies of the data can be obtained free of charge on appli-
cation to CCDC, 12 Union Road, Cambridge CB2 1EZ, UK
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Supporting Information
Complete analytical data for all the synthesized novel com-
pounds are given in the supporting information.
Acknowledgements
This work was supported by Deutsche Forschungsgemein-
schaft (Sonderforschungsbereich 424) and the Fonds der
Chemische Industrie. R. P. S. gratefully acknowledges the In-
ternational NRW Graduate School of Chemistry, Münster,
Germany, for doctoral scholarship.
References
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