G. Jones, C. J. Richards / Tetrahedron Letters 42 (2001) 5553–5555
5555
8. Phillips, A. J.; Uto, Y.; Wipf, P.; Reno, M. J.; Williams,
D. R. Org. Lett. 2000, 2, 1165.
Spectrometry Service Centre, University of Wales,
Swansea.
9. Compound 4a: lH (CDCl3) 3.41 (2H, t, J 9.0, 2×CHHO),
3.70–3.76 (1H, m, CHHO), 3.80–3.99 (2H, m, CHHO
and CHN), 4.65 (1H, brs, Cp), 4.72 (1H, brs, Cp), 4.96
(1H, brs, Cp), 5.08 (1H, brs, Cp), 7.01–7.41 (30H, m, Ph);
lP {1H} 115.7 (OPPh2).
References
1. Helmchen, G.; Pfaltz, A. Acc. Chem. Res. 2000, 33, 336.
2. (a) von Matt, P.; Pfaltz, A. Angew. Chem., Int. Ed. Engl.
1993, 32, 566; (b) Sprinz, J.; Helmchen, G. Tetrahedron
Lett. 1993, 34, 1769; (c) Dawson, G. J.; Frost, C. G.;
Williams, J. M. J. Tetrahedron Lett. 1993, 34, 3149.
3. (a) Richards, C. J.; Damalidis, T.; Hibbs, D. E.; Hurst-
house, M. B. Synlett 1995, 74; (b) Nishibayashi, Y.;
Uemura, S. Synlett 1995, 79; (c) Zhang, W.; Hirao, T.;
Ikeda, I. Tetrahedron Lett. 1996, 37, 4545; (d) Ahn, K.
H.; Cho, C.-W.; Park, J.; Lee, S. Tetrahedron: Asymmetry
1997, 8, 1179; (e) See also: Kudis, S.; Helmchen, G.
Angew. Chem., Int. Ed. Engl. 1998, 37, 3047.
4. Gilbertson, S. R.; Chang, C.-W. T. J. Org. Chem. 1998,
63, 8424.
5. (a) Hou, D.-R.; Burgess, K. Org. Lett. 1999, 1, 1745; (b)
Hou, D.-R.; Reibenspies, J. H.; Burgess, K. J. Org.
Chem. 2001, 66, 206.
Compound 4b: lH (CDCl3) 3.11 (1H, q, J 8.9, CHHO),
3.69–3.78 (1H, m, CHHO), 3.82 (1H, t, J 8.9, CHHO),
3.89–4.07 (2H, m, CHHO and CHN), 4.28 (2H, s, Cp),
4.63 (1H, s, Cp), 4.66 (1H, s, Cp), 6.87–7.09 (25H, m,
Ph), 7.12–7.29 (6H, m, Ph), 7.30–7.39 (4H, m, Ph); lP
{1H} 115.5 (OPPh2).
Compound 4c: lH (CDCl3) 3.77–3.82 (1H, m, CHHO),
3.95–4.00 (1H, m, CHHO), 4.06 (5H, s, Cp), 4.22–4.34
(3H, m, CH2O and CHN), 4.24 (2H, s, Cp), 4.64 (2H, s,
Cp), 7.20–7.30 (6H, m, Ph), 7.37–7.43 (4H, m, Ph); lP
{1H} 115.3 (OPPh2).
Compound 4d: lH (CDCl3) 1.59 (6H, brs, 3×CH2), 1.78
(6H, brs, 3×CH2), 1.97 (3H, brs, 3×CH), 3.76–3.80 (1H,
m, CHHO), 3.86–4.25 (4H, m, 3×CHHO+CHN), 7.21–
7.33 (4H, m, Ph), 7.34–7.50 (4H, m, Ph), 7.61–7.78 (2H,
m, Ph); lP {1H} 115.0 (OPPh2).
Compound 4e: lH (CDCl3) 3.87–3.93 (1H, m, -CHHO-),
4.04–4.06 (1H, m, -CHHO-), 4.36 (2H, dd, J 7.9 3.1,
-CH2O-), 4.43–4.51 (1H, m, -CHN-), 7.15–7.42 (13H, m,
Ph), 7.82–7.84 (2H, m, Ph); lP {1H} (CDCl3) 116.4
(-OPPh2).
6. (a) Yonehara, K.; Hashizume, T.; Mori, K.; Ohe, K.;
Uemura, S. J. Org. Chem. 1999, 64, 9374; (b) Yonehara,
K.; Mori, K.; Hashizume, T.; Chung, K.-G.; Ohe, K.;
Uemura, S. J. Organomet. Chem. 2000, 603, 40; (c)
Hashizume, T.; Yonehara, K.; Ohe, K.; Uemura, S. J.
Org. Chem. 2000, 65, 5197.
10. For notable exceptions, see: (a) Trost, B. M.; Krueger, A.
C.; Bunt, R. C.; Zambrano, J. J. Am. Chem. Soc. 1996,
118, 6520; (b) Wiese, B.; Helmchen, G. Tetrahedron Lett.
1998, 39, 5727.
7. Jones, G.; Butler, D. C. D.; Richards, C. J. Tetrahedron
Lett. 2000, 41, 9351.
.