S. Satishkumar, M. Periasamy / Tetrahedron: Asymmetry 17 (2006) 1116–1119
1119
25
(c 0.22, hexane), lit.12 ½aꢂD ¼ ꢀ307 (c 0.31, hexane). The
Periasamy, M.; Sivakumar, S.; Reddy, M. N. Synthesis 2003,
13, 965–967; Periasamy, M.; Ramanathan, C. R.; Sampath
Kumar, N. Tetrahedron: Asymmetry 1999, 10, 2307–2310.
7. Padmaja, M.; Periasamy, M. Tetrahedron: Asymmetry 2004,
15, 2437–2441; Periasamy, M.; Sreenivasaperumal, M.; Pad-
maja, M.; Rao, V. D. ARKIVOC 2004, 8, 4–11.
8. Spielman, M. A. J. Am. Chem. Soc. 1935, 57, 583–585.
9. Li, Z.; Xu, X.; Peng, Y.; Jiang, Z.; Ding, C.; Qian, X.
Synthesis 2005, 8, 1228–1230; Sucholeiki, I.; Lynch, V.; Phan,
L.; Wilcox, C. S. J. Org. Chem. 1988, 53, 98–104.
(S,S)-1 isomer with 41% ee was further enriched by repeat-
ing the resolution experiment using dibenzoyl-D-tartaric
25
acid to obtain the sample of 99% ee. ½aꢂD ¼ þ279 (c 0.22,
25
hexane), lit.12 ½aꢂD ¼ þ287 ꢃ 7 (c 0.281, hexane). The
samples were also analyzed by HPLC using a chiral column
to assess the enantiomeric purities.18
Acknowledgements
10. Mason, S. F.; Vane, G. W.; Schofield, K.; Wells, R. J.;
Whitehurst, J. S. J. Chem. Soc. B 1967, 553–556; Mason, S. F.
Molecular Optical Activity and the Chiral Discriminations;
Cambridge Univ. Press: Cambridge, UK, 1982; p 191.
11. Crystal data: For complex (ꢀ)-1Æ(ꢀ)-2 molecular formula:
C35H32N2O8, MW = 608.63, monoclinic, space group: P21,
We thank the CSIR (New Delhi), for a research fellowship
to S.S.K. We also thank the DST for the 400 MHz NMR
facility under FIST program and for the National single
crystal X-ray difractometer facility. Support of the UGC
under the ‘University of Potential for Excellence’ and the
Center for Advanced Study (CAS) programs is gratefully
acknowledged.
˚
˚
˚
a = 8.1272(6) A, b = 18.1103(14) A, c = 10.4433 (8) A, b =
3
˚
90.5680(10)ꢁ, V = 1537.03 A , Z = 1 (Z = 0), qc = 1.315
mg mꢀ3, l = 0.094 mmꢀ1, T = 293(2) K. Of the 18,006 reflec-
tions collected, 7210 were unique (Rint = 0.0452). Refinement
on all data converged at R1 = 0.0438, wR2 = 0.0667 (Depo-
sition number CCDC 600979).
12. Wilen, S. H.; Qi, J. Z. J. Org. Chem. 1991, 56, 485–487.
13. Harmata, M.; Kahaman, M. Tetrahedron: Asymmetry 2000,
11, 2875–2879; Blaser, H. U.; Jalett, H. P.; Lottenbach, W.;
Studer, M. J. Am. Chem. Soc. 2000, 122, 12675–12682.
14. Bag, B. G.; Kiedrowski, G. Angew. Chem., Int. Ed. 1999, 38,
3713–3714.
References
1. Tro¨ger, J. J. Prakt. Chem. 1887, 36, 225–245.
2. Bag, B. G. Curr. Sci. 1995, 68, 279–288.
3. Prelog, V.; Wieland, P. Helv. Chim. Acta 1944, 27, 1127–
1134.
15. Wilcox, C. S. Tetrahedron Lett. 1985, 26, 5749–5752; Bailly,
C.; Laine, W.; Demeunynck, M.; Lhomme, J. Biochem.
Biophys. Res. Commun. 2000, 273, 681–685; Goswami, S.;
Ghosh, K.; Dasgupta, S. J. Org. Chem. 2000, 65, 1907–1914;
Adrian, J. C., Jr.; Wilcox, C. S. J. Am. Chem. Soc. 1989, 111,
8055–8057; Weber, E.; Muller, U.; Wrosch, D.; Vogtle, F.;
Will, G.; Kirfel, A. J. Chem. Soc., Chem. Commun. 1985,
1578–1580.
16. Wilcox, C. S.; Geer, L. M.; Lynch, V. J. J. Am. Chem. Soc.
1987, 109, 1865–1867.
17. Pardo, C.; Sesmilo, E.; Gutierrez-Puebla, E.; Angeles, M.
J. Org. Chem. 2001, 66, 1607–1611.
4. Hesse, G.; Hargel, R. Liebigs Ann. Chem. 1976, 996–1008;
Lindner, K. R.; Mannschreck, A. J. Chromatogr. 1980, 193,
308–310; Saigo, K.; Chen, Y.; Kubota, N.; Tachibana, K.;
Yonezawa, N.; Hasegawa, M. Chem. Lett. 1986, 515–518.
5. Periasamy, M.; Venkatraman, L.; Sivakumar, S.; Sampath
Kumar, N.; Ramanathan, C. R. J. Org. Chem. 1999, 64,
7643–7645; Periasamy, M.; Ramanathan, C. R.; Bhanu
Prasad, A. S.; Bhaskar Kanth, J. V. Enantiomer 1998, 3, 3–
7; Periasamy, M.; Venkatraman, L.; Thomas, K. R. J. J. Org.
Chem. 1997, 62, 4302–4306; Venkatraman, L.; Periasamy, M.
Tetrahedron: Asymmetry 1996, 7, 2471–2474; Periasamy, M.;
Bhanu Prasad, A. S.; Bhaskar Kanth, J. V.; Kishan Reddy,
Ch. Tetrahedron: Asymmetry 1995, 6, 341–344.
18. HPLC analysis of 1 was carried out on a CHIRALCEL OJ-H
column using ethanol as mobile phase, flow rate: 0.5 mL/min.
Retention times, tR = 12.15 min for (S,S)-isomer and
tR = 40.78 min for (R,R)-isomer.
6. Periasamy, M.; Sivakumar, S.; Reddy, M. N.; Padmaja, M.
Org. Lett. 2004, 6, 265–268; Periasamy, M.; Reddy, M. N.;
Anwar, S. Tetrahedron: Asymmetry 2004, 15, 1809–1812;