H. M. Lee et al. / Tetrahedron: Asymmetry 12 (2001) 1537–1541
1541
25.45, 23.58, 11.29. HRMS (FAB+) calcd for
[C30H34N4O4+H+]: 515.2658. Found: 515.2642.
1997, 38, 2577; (l) Petri, A.; Pini, D.; Rapaccinni, S.;
Salvadori, P. Chirality 1999, 11, 745.
10. Inagaki, M.; Hiratake, J.; Yamamoto, Y.; Oda, J. Bull.
Chem. Soc. Jpn. 1987, 60, 4121.
4. (a) Han, H.; Janda, K. D. J. Am. Chem. Soc. 1996, 118,
7632; (b) Han, H.; Janda, K. D. Tetrahedron Lett. 1997,
38, 1527; (c) Bolm, C.; Gerlach, A. Angew. Chem., Int.
Ed. Engl. 1997, 36, 741.
5. (a) Lohray, B. B.; Nandanan, E.; Bhushan, V. Tetra-
hedron: Asymmetry 1996, 7, 2805; (b) Song, C. E.; Yang,
J. W.; Ha, H. J. Tetrahedron: Asymmetry 1997, 8, 841; (c)
Bolm, C.; Maischak, A.; Gerlach, A. Chem. Commun.
1997, 2353.
6. (a) Kresge, C. T.; Leonowicz, M. E.; Roth, W. J.; Vartuli,
J. C.; Beck, J. S. Nature 1992, 359, 710; (b) Zhao, D.;
Feng, J.; Huo, Q.; Melosh, N.; Fredrickson, G. H.;
Chmelka, B. F.; Stucky, G. D. Science 1998, 279, 548; (c)
Ying, J. Y.; Mehnert, C. P.; Wong, M. S. Angew. Chem.,
Int. Ed. 1999, 38, 57.
7. For results from this laboratory, see: (a) Bae, S. J.; Kim,
S.-W.; Hyeon, T.; Kim, B. M. Chem. Commun. 2000, 31;
(b) Kim, S.-W.; Bae, S. J.; Hyeon, T.; Kim, B. M.
Micropor. Mesopor. Mater. 2001, 44–45, 523.
11. Compound 5a: [h]D24=+109.9 (c 0.5, CHCl3); 1H NMR
(300 MHz, CDCl3): l 0.83 (t, J=8.0 Hz, 3H), 1.25–2.63
(m, 25H), 2.68 (t, J=6.7 Hz, 2H), 2.96–3.50 (m, 6H), 3.69
(t, J=6.7 Hz, 2H), 3.91 (s, 3H), 3.94 (s, 3H), 7.04 (d,
J=5.3 Hz, 2H), 7.32–7.43 (m, 4H), 7.90–8.02 (m, 4H),
8.31–8.34 (m, 2H), 8.64 (t, J=4.3 Hz, 2H); 13C NMR (75
MHz, CDCl3): l 157.83, 156.41, 147.36, 147.29, 146.93,
144.77, 144.54, 133.52, 132.40, 132.02, 131.57, 130.88,
129.52, 128.81, 127.26, 127.17, 122.88, 122.50, 122.14,
121.96, 118.43, 118.25, 102.04, 101.97, 75.94, 60.34, 60.02,
59.90, 59.22, 58.32, 58.02, 55.82, 42.87, 42.67, 38.74,
37.29, 35.38, 34.82, 34.77, 29.77, 28.93, 28.31, 27.66,
25.69, 25.41, 23.76, 22.99, 12.04. HRMS (FAB+) calcd for
[C50H58N6O5S+H+]: 855.4268. Found: 855.4246.
Compound 5b: [h]D30=+114.8 (c 1.0, CHCl3); 1H NMR
(300 MHz, CDCl3): l 0.83 (t, J=8.0 Hz, 3H), 1.25–2.71
(m, 35H), 2.95–3.56 (m, 6H), 3.64 (t, J=7.3 Hz, 2H), 3.91
(s, 3H), 3.92 (s, 3H), 7.02 (d, J=5.8 Hz, 2H), 7.36 (dd,
J=10 Hz and 3.0 Hz, 2H), 7.42 (d, J=5.1 Hz, 2H), 7.60
(m, 2H), 7.91–8.04 (m, 4H), 8.30–8.34 (m, 2H), 8.64 (dd,
J=5.0 Hz and 2.0 Hz, 2H); 13C NMR (75 MHz, CDCl3):
l 157.79, 156.44, 147.40, 144.81, 144.76, 132.33, 131.61,
128.82, 127.29, 122.88, 122.84, 122.54, 121.92, 118.43,
118.25, 102.11, 102.10, 77.22, 62.84, 60.11, 58.48, 58.18,
55.78, 42.87, 42.73, 39.49, 39.07, 37.53, 34.90, 32.62,
32.24, 30.21, 29.71, 29.56, 28.63, 27.73, 25.72, 25.49,
25.38, 25.16, 12.10. HRMS (FAB+) calcd for
[C54H66N6O5S+H+]: 911.4894. Found: 911.4919.
8. (a) Johnson, B. F. G.; Raynor, S. A.; Shephard, D. S.;
Mashmeyer, T.; Thomas, J. M.; Sankar, G.; Bromley, S.;
Oldroyd, R.; Gladden, L.; Mantle, M. D. Chem. Com-
mun. 1999, 1167; (b) Kim, G.-J.; Shin, J.-H. Tetrahedron
Lett. 1999, 40, 6827; (c) Zhou, X.-G.; Yu, X.-Q.; Huang,
J.-S.; Li, S.-G.; Li, L.-S.; Che, C.-M. Chem. Commun.
1999, 1789; (d) Piaggio, P.; McMorn, P.; Langham, C.;
Bethell, D.; Bulman-Page, P. C.; Hancock, F. E.; Hutch-
ings, G. J. New J. Chem. 1998, 1167; (e) Bellocq, N.;
Abrmason, M.; Lasperas, M.; Brunel, D.; Moreau, P.
Tetrahedron: Asymmetry 1999, 10, 3229.
12. Kaldor, S. W.; Hammond, M. Tetrahedron Lett. 1991,
32, 5043.
1
9. Compound 2: [h]3D0=+29.1 (c 1.0, EtOH); H NMR (300
MHz, CDCl3): l 0.87 (t, J=7.2 Hz, 3H), 1.32–2.00 (m,
9H), 2.46–2.70 (m, 3H), 3.10–3.59 (m, 3H), 3.71–3.97 (m,
5H), 4.56 (q, J=5.1 Hz, 2H), 7.20 (d, J=5.3 Hz, 1H),
7.32 (dd, J=10 Hz and 3.0 Hz, 1H), 7.46 (d, J=4.6 Hz,
1H), 7.64 (d, J=2.7 Hz, 1H), 7.90–7.99 (m, 2H), 8.18 (d,
J=1.5 Hz, 1H), 8.35 (d, J=7.2 Hz, 1H), 8.65 (d, J=4.5
Hz, 1H); 13C NMR (300 MHz, CDCl3): l 157.68, 156.44,
147.42, 144.83, 144.78, 132.28, 131.59, 127.29, 122.84,
122.53, 122.47, 121.86, 121.74, 118.46, 102.06, 60.07,
58.52, 55.72, 46.21, 42.85, 37.54, 28.65, 27.75, 25.58,
13. The difference in the grafting amount is presumed to
result from the different chain lengths of the ligands.
Both L1 and L2, which have shorter linkers than L3,
exhibit lower degrees of grafting than L3.
14. (a) Sharpless, K. B.; Amberg, W.; Beller, M.; Chen, H.;
Hartung, J.; Kawanami, Y.; Lubben, D.; Manoury, E.;
Ogino, Y.; Shibata, T.; Ukita, T. J. Org. Chem. 1991, 56,
4585; (b) Norrby, P.-O.; Rasmussen, T.; Haller, J.;
Strassner, T.; Houk, K. N. J. Am. Chem. Soc. 1999, 121,
10186.
.