T. Bak ꢀo et al. / Tetrahedron: Asymmetry 15 (2004) 1589–1595
1595
collected of which 5385 were unique [Rint ¼ 0:0113,
Rr ¼ 0:0140]; intensities of 4494 reflections were greater
1457; (d) Porter, M. J.; Roberts, S. M.; Skidmore, J.
Bioorg. Med. Chem. 1999, 7, 2145; (e) Porter, M. J.;
Skidmore, J. Chem. Commun. 2000, 1215.
22
than 2rðIÞ, completeness to 2h ¼ 1:000. A semi-
23
7. (a) Shibasaki, M.; Sasai, H.; Arai, T. Angew. Chem., Int.
Ed. 1997, 36, 1237; (b) Yamada, K.; Arai, T.; Sasai, H.;
Shibasaki, M. J. Org. Chem. 1998, 63, 3666; (c) Watanabe,
S.; Arai, T.; Sasai, H.; Bougauchi, M.; Shibasaki, M.
J. Org. Chem. 1998, 63, 8090.
. Elston, C. L.; Jackson, R. W. F.; MacDonald, S. J. F.;
Murray, P. J. Angew. Chem., Int. Ed. 1997, 36, 410.
9. Baccin, C.; Gusso, A.; Pinna, F.; Strukul, G. Organomet-
allics 1995, 14, 1161.
empirical (w-scan) absorption correction was applied
to the data (the minimum and maximum transmission
factors were 0.930 and 0.991). The structure was solved
2
4
by direct methods.
squares refinement on F for all nonhydrogen atoms
yielded R ¼ 0:0383 and wR ¼ 0:1171 for 4494
Anisotropic full-matrix least-
2
25
8
1
2
[
I > 2rðIÞ] and R
1
¼ 0:0468 and wR
2
¼ 0:1227 for all
(
5385) intensity data. Number of parameters ¼ 438,
1
0. (a) Enders, D.; Zhu, J.; Raabe, G. Angew. Chem., Int. Ed.
1996, 35, 1725; (b) Enders, D.; Kramps, L.; Zhu, J.
Tetrahedron: Asymmetry 1998, 9, 39597.
goodness-of-fit ¼ 1.083; the maximum and mean shift/
esd 0.561 and 0.068; extinction coefficient ¼ 0.0074(6).
The maximum and minimum residual electron density in
3
1
1. (a) Pluim, H.; Wynberg, H. J. Org. Chem. 1980, 45, 2498;
b) Baba, N.; Oda, J.; Kawahara, S.; Hamada, M. Bull.
ꢁ
the final difference map was 0.129 and ꢀ0.137 e/A .
(
26
Absolute structure parameter x ¼ 0:1ð2Þ. Hydrogen
Inst. Chem. Res. Kyoto Univ. 1989, 67, 121; (c) Lygo, B.;
Wainwright, P. G. Tetrahedron 1999, 55, 6289; (d) Corey,
E. J.; Zhang, F.-Y. Org. Lett. 1999, 1, 1287; (e) Arai, S.;
Tsuge, H.; Shioiri, T. Tetrahedron Lett. 1998, 39, 7563; (f)
Arai, S.; Oku, M.; Miura, M.; Shioiri, T. Synlett 1998,
atom positions were located in difference maps and were
refined. (ORTEP diagram ) CCDC number 233942.
27
1
201.
1
2. (a) Bak oꢀ , P.; T o} ke, L. J. Incl. Phenom. 1995, 23, 195; (b)
Acknowledgements
ꢀ
Bak oꢀ , P.; Bak oꢀ , T.; Bisztray, K.; Sz o€ ll o} sy, A.; Nagy, K.;
T o} ke, L. J. Incl. Phenom. 2001, 39, 247.
The authors are grateful to OTKA for the financial
support of this research (Grant Nos T 042514 and
1
1
3. Marsman, B.; Wynberg, H. J. Org. Chem. 1979, 44, 2312.
4. Juli ꢀa , S.; Guixer, J.; Masana, J.; Rocas, J.; Colonna, S.;
Annuziata, R. J. Chem. Soc., Perkin Trans. 1 1982, 1317.
5. Washington, I.; Houk, K. N. Org. Lett. 2002, 4, 2661.
6. Lightner, D. A. In Circular Dichroism, Principles and
Applications; Berova, N., Nakanashi, K., Woody, R. W.,
Eds.; Wiley: New York, 2000; p 261.
0
42546). They thank Prof. M. Hollosy for discussions.
1
1
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