3064
W. H. Midura, M. Mikołajczyk / Tetrahedron Letters 43 (2002) 3061–3065
Scheme 5.
active isomers of 1 is currently being studied in our
laboratory.
Tetrahedron: Asymmetry 1997, 8, 3991–3994.
7. Midura, W. H.; Krysiak, J. A.; Wieczorek, M. W.;
Majzner, R.; Mikołajczyk, M. Chem. Commun. 1998,
1109–1110.
Acknowledgements
8. Mikołajczyk, M.; Midura, W. H.; Grzejszczak, S.;
Zatorski, A.; Chefczyn´ska, A. J. Org. Chem. 1978, 43,
473–478.
Partial financial support by the State Committee for
Scientific Research (Grant No Z-005/t09/99) is grate-
fully acknowledged.
9. For this new procedure of the Horner–Wittig reaction of
a-phosphoryl sulfoxides see: Shen, J.; Jing, G.-F. Synthe-
sis 2000, 99–102.
10. E-(S)-3: [h]D=+3.2 (c 3.2, acetone); 31P NMR (CDCl3):
12.8 ppm; 1H NMR (500 MHz, CDCl3): 2.39 (s, 3H),
3.28 (d, 3H, J=11.6 Hz), 3.47 (d, 3H, J=11.7 Hz),
7.27–7.29 (m, 3H), 7.41–7.43 (m, 2H), 7.65–7.67 (m, 2H),
7.75–7.77 (m, 2H), 8.09 (d, 1H, J=41.7 Hz). Calcd for
C17H19O4PS: C, 58.28; H, 5.47. Found: C, 58.37; H, 5.42.
Z-(S)-3: [h]D=−367.0 (c 2.6, C6H6); 31P NMR (CDCl3):
16.4 ppm; 1H NMR (200 MHz, CDCl3): 2.38 (s, 3H),
3.26 (d, 3H, J=11.5 Hz), 3.80 (d, 3H, J=11.6 Hz),
7.25–7.29 (m, 2H), 7.42–7.49 (m, 5H), 7.65–7.70 (m, 2H),
8.18 (d, 1H, J=21.8 Hz).
References
1. Aminophosphonic and Aminophosphinic Acids, Chemistry
and Biological Activity; Kukhar, V. P.; Hudson, H. R.,
Eds.; John Wiley & Sons: Chichester, 2000.
2. (a) Giannis, A.; Kolter, T. Angew. Chem., Int. Ed. Engl.
1993, 32, 1244–1267; (b) Gante, J. Angew. Chem., Int. Ed.
Engl. 1994, 33, 1699–1720.
3. (a) Reissig, H. U. In The Chemistry of the Cyclopropyl
Group; Patai, S.; Rappaport, Z., Eds.; John Wiley &
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Med. Chem. 1995, 2, 511.
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1
11. 6a%: H NMR (200 MHz, CDCl3): 2.45 (s, 3H), 3.02 (d,
3H, J=11.4 Hz), 3.42 (dd, 1H, J=8.3, 16.9 Hz), 3.54 (d,
3H, J=11.1 Hz), 3.78 (dd, 1H, J=8.3, 13.4 Hz), 3.82 (s,
3H), 7.15–7.37 (m, 7H), 7.70–7.74 (m, 2H); 13C NMR
(50.3 Hz) 21.48, 25.53, 31.91, 47.96 (d, J=174.2 Hz),
52.63 (d, J=24.5 Hz), 61.79 (d, J=42.7 Hz), 127.26,
127.94, 128.97, 129.1, 133.0, (d, J=5.1 Hz), 139.3, 142.3,
166.62 (d, J=2.0 Hz). Calcd for C20H23O6PS: C, 56.87;
H, 5.49. Found: C, 56.65; H, 5.52.
5. Hanessian, S.; Cantin, L.-D.; Roy, S.; Andreotti, D.;
Gomtsyan, A. Tetrahedron Lett. 1997, 38, 1103–1106.
6. (a) Mikołajczyk, M.; Łyz
zorek, M. W.; Błaszczyk, J. Chem. Commun. 1996, 1503–
1504; (b) Mikołajczyk, M.; Łyzwa, P.; Drabowicz, J.
; wa, P.; Drabowicz, J.; Wiec-
12. For the spectral criteria used for the determination of the
relative configuration in cyclopropylphosphonates see:
;