Y.-Q. Kuang et al. / Tetrahedron Letters 43 (2002) 3669–3671
3671
mL, 0.01 mmol). For trans-1,2-disubstituted olefins,
CH3SO2NH2 (190 mg, 2.0 mmol) was added. The solu-
tion was cooled to 0°C (with the exception of trans-b-
methylstyrene, entry 6 in Table 1) and the olefin (2.0
mmol) was added. The mixture was stirred vigorously
at 0°C for 24 h. While the mixture was stirred at 0°C,
Na2SO3 (2.5 g) was added and the mixture was allowed
to warm to room temperature and stirred for 45 min.
CH2Cl2 (20 mL) was added to the reaction mixture, and
after separation of the layers the aqueous phase was
further extracted with CH2Cl2 (10 mL×3) (if
CH3SO2NH2 was used, the combined organic layers
were washed with 2 mol L−1 NaOH). The combined
organic layers were dried over anhydrous Na2SO4 and
evaporated to dryness under reduced pressure. The
residue was dissolved in CH2Cl2 (10 mL) and dry Et2O
(50 mL) was slowly added to the solution under vigor-
ous stirring conditions. The precipitate obtained was
collected by filtration, washed with cool Et2O/EtOH
(3:1) and Et2O, and dried in vacuo. The filtrate was
evaporated to give the crude product, which was fur-
ther purified by column chromatography to afford the
pure diol.
5. Canali, L.; Song, C. E.; Sherrington, D. C. Tetrahedron:
Asymmetry 1998, 9, 1029–1034.
6. (a) Han, H.; Janda, K. D. Tetrahedron Lett. 1997, 38,
1527–1530; (b) Bolm, C.; Gerlach, A. Angew. Chem., Int.
Ed. Engl. 1997, 36, 741–743; (c) Kuang, Y. Q.; Zhang, S.
Y.; Wei, L. L. Tetrahedron Lett. 2001, 42, 5925–5927.
7. Salvadori, P.; Pini, D.; Petri, A. J. Am. Chem. Soc. 1997,
119, 6929–6930.
8. Sharpless, K. B.; Amberg, W.; Bennani, Y. L.; Crispino,
G. A.; Hartung, J.; Jeong, K. S.; Kwong, H. L.;
Morikawa, K.; Wang, Z. M.; Xu, D. Q.; Zhang, X. L. J.
Org. Chem. 1992, 57, 2768–2771.
9. (a) Petri, A.; Pini, D.; Rapaccini, S.; Salvadori, P. Chiral-
ity 1995, 7, 580–585; (b) Pini, D.; Petri, A.; Salvadori, P.
Tetrahedron 1994, 38, 11321–11328.
10. Song, C. E.; Yang, J. W.; Ha, H. J.; Lee, S. G. Tetra-
hedron: Asymmetry 1996, 7, 645–648.
11. Compound 3: Mp 139–141.5°C; 1H NMR (400 MHz,
CDCl3): l 8.63 (d, J=4.4 Hz, 2H), 8.32 (m, 2H), 7.99 (d,
J=9.2 Hz, 2H), 7.96 (m, 2H), 7.58 (d, J=2.0 Hz, 2H),
7.42 (d, J=4.8 Hz, 2H), 7.38 (d, J=8.8 Hz, 1H), 7.36 (d,
J=9.2 Hz, 1H), 7.04 (s, 2H), 3.92 (s, 6H), 3.68 (m, 4H),
3.46 (m, 2H), 3.07 (m, 4H), 2.32–2.70 (m, 16H), 1.55–1.82
(m, 14H); 13C NMR (100 MHz, CDCl3): l 157.85,
156.44, 147.34, 144.72, 132.42, 131.55, 127.29, 122.84,
122.51, 121.97, 118.41, 102.09, 76.10, 60.43, 60.09, 58.10,
55.80, 42.71, 35.38, 34.86, 34.82, 29.85, 28.40, 25.71,
23.55; HRMS (ESI): calcd for C52H62N6O6S2+H:
931.4251, found: 931.4237. Anal. calcd for C52H62N6O6S:
C, 67.07; H, 6.72; N, 9.03; S, 6.87. Found: C, 66.89; H,
6.62; N, 8.85; S, 6.72%.
Acknowledgements
We thank National Natural Science Foundation of
China (NSFC) for financial support.
12. Compound 1: Mp 173–174.5°C; 1H NMR (400 MHz,
CDCl3): l 8.62 (d, J=4.4 Hz, 2H), 8.31 (m, 2H), 7.97 (d,
J=9.2 Hz, 2H), 7.96 (m, 2H), 7.58 (d, J=2.4 Hz, 2H),
7.43 (d, J=4.4 Hz, 2H), 7.36 (d, J=9.2 Hz, 1H), 7.35 (d,
J=9.2 Hz, 1H), 6.99 (d, J=5.6 Hz, 2H), 4.06 (t, J=5.2
Hz, 4H), 3.90 (s, 6H), 3.48 (m, 2H), 3.16 (m, 6H), 3.01
(m, 6H), 2.53 (m, 2H), 2.36 (m, 2H), 1.60–1.92 (m, 16H);
13C NMR (100 MHz, CDCl3): l 157.86, 156.46, 147.17,
144.70, 144.45, 132.59, 131.27, 127.29, 122.81, 122.37,
121.96, 118.56, 102.13, 75.88, 60.01, 57.50, 56.16, 55.75,
55.32, 53.02, 42.48, 34.57, 28.10, 26.23, 25.65, 23.46;
HRMS (ESI): calcd for C52H62N6O10S2+H: 995.4047,
found 995.4039. Anal. calcd for C52H62N6O10S2: C, 62.75;
H, 6.28; N, 8.45; S, 6.43. Found: C, 62.41; H, 6.52; N,
8.11; S, 6.29%.
References
1. For reviews, see: (a) Kolb, H. C.; Van Nieuwenhze, M.
S.; Sharpless, K. B. Chem. Rev. 1994, 94, 2483–2547; (b)
Beller, M.; Sharpless, K. B. In Applied Homogeneous
Catalysis; Cornil, B.; Herrmann, W. A.; Eds.; VCH:
Weinheim, 1996; pp. 1009–1024; (c) Marko, I. E.; Svend-
sen, J. S. In Comprehensive Asymmetric Catalysis; Jacob-
sen, E. N.; Pfaltz, A.; Yamamoto, H.; Eds.; Springer:
Berlin, 1999; pp. 713–787.
2. (a) Bolm, C.; Gerlach, A. Eur. J. Org. Chem. 1998, 21–27
and references cited therein; (b) Kobayashi, S.; Endo, M.;
Nagayama, S. J. Am. Chem. Soc. 1999, 121, 11229–
11230; (c) Kobayashi, S.; Ishida, T.; Akiyama, R. Org.
Lett. 2001, 3, 2649–2652; (d) Choudary, B. M.; Chow-
dari, N. S.; Kantam, M. L.; Raghavan, K. V. J. Am.
Chem. Soc. 2001, 123, 9220–9221; (e) Motorina, I.; Crud-
den, C. M. Org. Lett. 2001, 3, 2325–2328.
3. (a) Salvadori, P.; Pini, D.; Petri, A. Synlett 1999, 8,
1181–1190; (b) Petri, A.; Pini, D.; Rapaccini, S.; Sal-
vadori, P. Chirality 1999, 11, 745–751.
4. (a) Han, H.; Janda, K. D. J. Am. Chem. Soc. 1996, 118,
7632–7633; (b) Willis, M. J. Chem. Soc., Perkin Trans. 1
1998, 3101–3120; (c) Fan, Q. H.; Ren, C. Y.; Yeung, C.
H.; Hu, W. H.; Chan, A. S. C. J. Am. Chem. Soc. 1999,
121, 7407–7408.
13. Entry 1 (diol): Daicel Chiralcel OJ, hexane/iPrOH=4:1,
flow rate 0.6 mL/min, tR (min)=12.2 (minor), 13.8
(major); entry 2 (diol): Daicel Chiralcel OB-H, hexane/
iPrOH=9:1, flow rate 0.5 mL/min, tR (min)=14.7
(minor), 17.8 (major); entry 3 (diol): Daicel Chiralcel OD,
hexane/iPrOH=40:1, flow rate 1.0 mL/min, tR (min)=
27.8 (minor), 29.7 (major); entry 4 (diol): Daicel Chiralcel
OD, hexane/iPrOH=19:1, flow rate 1.0 mL/min, tR
(min)=14.1 (major), 20.6 (minor); entry 5 (bisbenzoate):
Daicel Chiralcel OD-H, hexane/iPrOH=500:1, flow rate
1.0 mL/min, tR (min)=6.3 (major), 7.5 (minor); entry 6
(diol): Daicel Chiralcel OD, hexane/iPrOH=20:1, flow
rate 1.0 mL/min, tR (min)=15.0 (minor), 16.4 (major).