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R. Mazurkiewicz, A. Kuz´nik / Tetrahedron Letters 47 (2006) 3439–3442
Shiraki, C.; Hirata, T. Chem. Pharm. Bull. 1989, 37, 275–
19. 1H NMR spectral data (300 MHz, CDCl3, d (ppm)) of 1a:
7.37–7.32 (m, 5H), 5.61 (br d, J = 8.7 Hz, 1H), 5.17 (d,
J = 12.3 Hz, 1H), 5.12 (d, J = 12.6 Hz, 1H), 4.93 (dd,
J = 22.4 Hz, J = 9.2 Hz, 1H), 3.84 (s, 3H), 3.83 (d, J =
9.0 Hz, 3H), 3.80 (d, J = 10.8 Hz, 3H); compound 1c:
6.68 (br d, J = 8.7 Hz, 1H), 5.26 (dd, J = 22.2 Hz,
J = 8.7 Hz, 1H), 3.84 (s, 3H), 3.84 (d, J = 10.8 Hz, 3H),
3.82 (d, J = 11.1 Hz, 3H), 2.09 (d, J = 0.6 Hz, 3H);
compound 1d: 6.41 (br d, J = 7.5 Hz, 1H), 5.25 (dd,
J = 22.2 Hz, J = 9.0 Hz, 1H), 3.84 (d, J = 0.6 Hz, 3H),
3.84 (d, J = 11.1 Hz, 3H), 3.80 (d, J = 11.1 Hz, 3H), 1.25
(s, 9H); compound 1e: 7.87–7.83 (m, 2H), 7.59–7.44 (m,
3H), 6.98 (br d, J = 7.5 Hz, 1H), 5.47 (dd, J = 22.1 Hz,
J = 8.9 Hz, 1H), 3.88 (d, J = 10.8 Hz, 3H), 3.87 (s, 3H),
3.83 (d, J = 10.8 Hz, 3H); compound 1f: 5.57 (br d,
J = 8.4 Hz, 1H), 4.92 (dd, J = 22.2 Hz, J = 9.3 Hz, 1H),
3.84 (s, 3H), 3.84 (d, J = 10.8 Hz, 3H), 3.83 (d,
J = 10.8 Hz, 3H), 3.73 (s, 3H); compound 1g: 5.36 (br d,
J = 8.4 Hz, 1H), 4.89 (dd, J = 22.8 Hz, J = 9.3 Hz, 1H),
3.84 (s, 3H), 3.84 (d, J = 10.8 Hz, 3H), 3.83 (d,
J = 10.8 Hz, 3H), 1.46 (s, 9H); compound 8a (Z): 7.38–
7.31 (m, 5H), 6.62 (t, J = 7.5 Hz, 1H), 6.20 (br s, 1H), 5.14
(s, 2H), 3.75 (s, 3H), 2.23 (dq, J = 7.5 Hz, J = 7.5 Hz, 2H),
1.06 (t, J = 7.7 Hz, 3H); compound 8a (E): 7.38–7.33 (m,
6H), 6.79 (br s, 1H), 5.14 (s, 2H), 3.81 (s, 3H), 2.57 (dq,
J = 7.5 Hz, J = 7.5 Hz, 2H), 1.08 (t, J = 7.7 Hz, 3H);
compound 8c: 12.58 (br s, 1H), 8.14 (d, J = 8.4 Hz, 1H),
7.94 (d, J = 8.7 Hz, 1H), 7.80 (d, J = 8.1 Hz, 1H), 7.77–
7.71 (m, 1H), 7.58–7.52 (m, 1H), 7.31 (d, J = 8.4 Hz, 1H),
6.35 (s, 1H), 3.91 (s, 3H), 2.29 (s, 3H); compound 8d: 6.81
(br s, 1H), 3.74 (s, 3H), 2.16 (d, J = 0.6 Hz, 3H), 1.82 (s,
3H), 1.27 (s, 9H).
279; (d) Hegedus, L. S.; Schultze, L. M.; Toro, J.; Yijun,
C. Tetrahedron 1985, 41, 5833–5838; (e) Hedewijn, P.;
Claes, P. J.; Vanderhaeghe, H. J. Med. Chem. 1986, 29,
661–664.
3. Scopes, D. I. C.; Kluge, A. F.; Edwards, J. A. J. Org.
Chem. 1977, 42, 376–377.
4. (a) Yoshida, A. T.; Tajima, Y.; Takeda, N.; Oida, S.
Tetrahedron Lett. 1984, 25, 2793–2796; (b) Huang, N. Z.;
Kalish, V. J.; Miller, M. J. Tetrahedron 1990, 46, 8067–
8074; (c) Seki, M.; Kondo, K.; Iwasaki, T. J. Chem. Soc.,
Perkin Trans. 1 1996, 1, 3–5.
5. Narukawa, Y.; Juneau, K. N.; Snustad, D.; Miller, D. B.;
Hegedus, L. S. J. Org. Chem. 1992, 57, 5453–5462.
6. (a) Aguado, G. P.; Moglioni, A. G.; Ortuno, R. M.
˜
Tetrahedron: Asymmetry 2003, 14, 217–223; (b) Williams,
R. M. Synthesis of Optically Active a-Amino Acids;
Pergamon Press: Oxford, 1989; pp 1–133; (c) Williams,
R. M. Aldrichim. Acta 1992, 25, 11–25.
7. (a) Brown, J. M. In Hydrogenation of Functionalized
Carbon–Carbon Double Bonds; Jacobsen, A., Pfaltz, H.,
Yamamoto, H., Eds.; Comprehensive Asymmetric Cata-
lysis; Springer: Berlin, 1999; Vol. I, pp 121–182; (b)
Tungler, A.; Fogassy, G. J. Mol. Catal. A: Chem. 2001,
173, 231–247; (c) Adamczyk, M.; Akireddy, S. R.; Reddy,
R. E. Tetrahedron 2002, 58, 6951–6963; (d) Aguado, G. P.;
Alvarez-Larena, A.; Illa, O.; Moglioni, A. G.; Ortuno, R.
˜
M. Tetrahedron: Asymmetry 2001, 12, 25–28; (e) Wang,
W.; Xiong, C.; Zhang, J.; Hruby, V. J. Tetrahedron 2002,
58, 3101–3110.
8. (a) Bagley, M. C.; Hind, S. L.; Moody, C. J. Tetrahedron
Lett. 2000, 41, 6897–6900; (b) Allen, J. R.; Danishefsky, S.
J. J. Prakt. Chem. 2000, 342, 736–744; (c) Mauldin, S. C.;
Hornback, W. J.; Munroe, J. E. J. Chem. Soc., Perkin
Trans. 1 2001, 13, 1554–1558.
9. Ferris, L.; Haigh, D.; Moody, C. J. J. Chem. Soc., Perkin
Trans. 1 1996, 2885–2888.
10. Shiraki, C.; Saito, H.; Takahashi, K.; Urakawa, C.;
Hirata, T. Synthesis 1988, 399–401.
11. Schmidt, U.; Lieberknecht, A.; Wild, J. Synthesis 1984,
53–60.
12. Mazurkiewicz, R.; Grymel, M. Monatsh. Chem. 1999, 130,
597–604.
13. Mazurkiewicz, R.; Grymel, M.; Kuz´nik, A. Monatsh.
Chem. 2004, 135, 799–806.
14. Mazurkiewicz, R.; Kuz´nik, A.; Grymel, M.; Kuz´nik, N.
Monatsh. Chem. 2004, 135, 807–815.
20. 13C NMR spectral data (75 MHz, CDCl3, d (ppm)/JC–P
(Hz)) of 1a: 167.2/2.2, 155.6/7.3, 135.8, 128.5, 128.3, 128.1,
67.6, 54.1/6.3, 54.0/7.0, 53.3, 52.0/147.2; compound 1c:
169.7/6.0, 167.1/2.0, 54.1/6.5, 53.9/6.4, 53.3, 49.9/146.6,
22.7; compound 1d: 178.0/5.2, 167.3/1.5, 54.2/6.5, 53.8/
7.0, 53.3, 50.0/146.2, 38.8, 27.2; compound 1e: 167.2/2.0,
166.8/5.5, 133.0, 132.2, 128.7, 127.3, 54.3/6.0, 54.0/7.1,
53.4, 50.4/146.7; compound 1f: 167.2/2.2, 156.2/8.0, 54.1/
6.4, 54.0/7.0, 53.3, 52.9, 52.0/147.2; compound 1g: 167.5/
3.0, 154.8/7.5, 54.1/6.0, 54.0/6.0, 53.3, 51.6/147.2, 29.7,
28.2; compound 8a (Z): 165.1, 154.0, 139.7, 136.0, 128.5,
128.2, 128.1, 124.6, 67.3, 52.3, 21.9, 12.7; compound 8a
(E): 164.5, 158.0, 136.1, 128.6, 128.3, 128.2, 124.0, 66.9,
52.2, 21.7, 14.2; compound 8c: 168.5, 165.7, 155.4, 146.6,
136.8, 135.4, 130.2, 128.3, 127.7, 126.8, 126.7, 123.2, 112.3,
52,7, 23.8; compound 8d: 177.0, 165.3, 145.4, 121.1, 51.7,
38.9, 27.4, 22.4, 21.2.
15. Benoiton, N. L. Biopolym. (Pept. Sci.) 1996, 40, 245–254.
16. Teoh, E.; Campi, E. M.; Jackson, W. R.; Robinson, A. J.
New J. Chem. 2003, 27, 387–394.
17. Coleman, R. S.; Carpenter, A. J. J. Org. Chem. 1993, 58,
4452–4461.
21. The results of C, H, N and P-microanalyses of 1d:
C10H20NO6P, calcd/found C 42.71/42.53, H 7.17/7.36,
N 4.98/5.22, P 11.01/11.07%; compound 8d: C11H19NO3,
18. Horenstein, B. A.; Nakanishi, K. J. Am. Chem. Soc. 1989,
111, 6242–6246.
calcd/found
6.55%.
C 61.95/61.76, H 8.98/8.98, N 6.57/