5652
M. Z. Gao et al. / Tetrahedron Letters 45 (2004) 5649–5652
ꢁ
Fritschi, H.; Leutenegger, U.; Pfaltz, A. Angew. Chem.,
Int. Ed. Engl. 1986, 25, 1005.
3. Doyle, M. P.; Protopopova, M. N. Tetrahedron 1998, 54,
7919; Doyle, M. P.; Forbes, D. C. Chem. Rev. 1998, 98,
911; Lebel, H.; Marcoux, J.-F.; Molinaro, C.; Charette,
A. B. Chem. Rev. 2003, 103, 977.
4. Aratani, T.; Yoneyoshi, Y.; Nagase, T. Tetrahedron Lett.
1975, 16, 1707; Aratani, T.; Yoneyoshi, Y.; Nagase, T.
Tetrahedron Lett. 1982, 23, 685.
5. Fukuda, T.; Katsuki, T. Tetrahedron 1997, 53, 7201;
Ikeno, T.; Sato, M.; Yamada, T. Chem. Lett. 1999, 1345.
6. Davies, H. M. L.; Bruzinski, P. R.; Lake, D. H.; Kong, N.;
Fall, M. J. J. Am. Chem. Soc. 1996, 118, 6897.
7. Lo, W.-C.; Che, C.-M.; Cheng, K.-F.; Mark, T. C. W.
J. Chem. Soc., Chem. Commun. 1997, 1205; Zhang, J.-L.;
Che, C.-M. Org. Lett. 2002, 4, 1911.
8. (a) Ghosh, A. K.; Mathivanan, P.; Cappiello, J. Tetrahe-
dron: Asymmetry 1998, 9, 1; (b) Gao, M. Z.; Wang, B.
Prog. Chem. 2002, 14(5), 347.
12. Benincori, T.; Brenna, E.; Sannicolo, F.; Trimarco, L.;
Antognazza, P.; Cesarotti, E.; Demartin, F.; Pilati, T. J.
Org. Chem. 1996, 61, 6244; Voituriez, A.; Schulz, E.
Tetrahedron: Asymmetry 2003, 14, 339.
13. Gao, M. Z.; Wang, B.; Liu, H. B.; Xu, Z. L. Chin. J.
Chem. 2002, 20(1), 85.
14. Selected data for 4d, (þ)-2,5-bis[40(S)-tert-butyloxazolin-
22
20-yl]thiophene: mp, 120–121 °C. ½aꢀ þ5.44 (c 0.55,
D
acetone). IR: 2958, 2903, 2875, 1945, 1534, 1479, 1362,
1305, 1252, 1212, 1066, 1014, 949, 831, 748, 675 cmꢁ1. H
1
NMR (CDCl3), dH: 0.97 [s, 18H, 2 ꢂ C(CH3)], 4.03 (dd,
J ¼ 7:5, 10.0 Hz, 2H, 2 ꢂ OCHH), 4.23 (dd, J ¼ 8:0,
8.5 Hz, 2H, 2 ꢂ NCH), 4.34 (dd, J ¼ 8:5, 10.0 Hz, 2H,
2 ꢂ OCHH), 7.52(s, H2 , thiophene-H);
13C NMR, dc:
25.79, 34.05, 53.79, 69.25, 129.91, 133.80, 158.39. MS
(FAB): 335 (Mþ1, 100%), 277, 223, 221, 179, 165, 95, 69;
Anal. Calcd for C18H24N2O2S: C, 64.64; H, 7.83; N, 8.37;
S, 9.58. Found: C, 64.97; H, 8.08; N, 8.14; S, 9.13.
15. Evans, D. A.; Scheidt, K. A.; Fandrick, K. R.; Lam, H.
W.; Wu, J. J. Am. Chem. Soc. 2003, 125, 10780.
16. Boulch, R.; Scheurer, A.; Mosset, P.; Saalfrank, R. W.
Tetrahedron Lett. 2000, 41, 1023.
9. Evans, D. A.; Woerpel, K. A.; Hinman, M. M.; Faul,
M. M. J. Am. Chem. Soc. 1991, 113, 726.
10. Nishiyama, H.; Itoh, Y.; Matsumoto, H.; Park, S.-B.;
Itoh, K. J. Am. Chem. Soc. 1994, 116, 2223; Nishiyama,
H.; Itoh, Y.; Sugawara, Y.; Matsumoto, H.; Aoki, K.;
Itoh, K. Bull. Chem. Soc. Jpn. 1995, 68, 1247; Gupta, A.
D.; Bhuniya, D.; Singh, V. K. Tetrahedron 1994, 50,
13725.
17. Kim, S.-G.; Cho, C.-W.; Ahn, K. H. Tetrahedron:
Asymmetry 1997, 8, 1023; Glos, M.; Reiser, O. Org. Lett.
2000, 2, 2045.
18. Sheldrick, G. M.; SHELXTL, version 5.03; Siemens Ana-
lytical X-ray Instruments: Madison, WI, 1995;
11. Uozurui, Y.; Kyota, H.; Kishi, E.; Kitayama, K.;
Hoyashi, T. Tetrahedron: Asymmmetry 1996, 7, 1603.
Sheldrick, G. M.; SHELX-96 Program for Crystal Structure
Determination; Bruker-AXS: Madison, WI, 1996.