2512
A. E. Wro´blewski, D. G. Piotrowska / Tetrahedron: Asymmetry 13 (2002) 2509–2512
In the same way, from crude aldehyde (S)-1 [prepared
from (S)-3 (0.668 g, 2.77 mmol)] and lithium O,O-
dimethyl phosphite (2.77 mmol), a 1:1 mixture of the
phosphonates (1S,2S)-10a and (1R,2S)-10b (0.490 g,
51%) was obtained after chromatography on a silica gel
column.
4. Matsunga, N.; Harada, H.; Aoyama, T.; Shioiri, T. Hete-
rocycles 1992, 33, 235–255.
5. Lee, K.-Y.; Kim, Y.-H.; Park, M.-S.; Oh, C.-Y.; Ham,
W.-H. J. Org. Chem. 1999, 64, 9450–9458.
6. Schade, W.; Reissig, H.-U. J. Prakt. Chem. 1999, 341,
685–686.
7. Ambroise, L.; Jackson, R. F. W. Tetrahedron Lett. 1996,
37, 2311–2314.
4.4. Phosphonates (1S,2S)-9a and (1S,2S)-10a
8. Barco, A.; Benetti, S.; Risi, C. D.; Pollini, G. P.; Romag-
noli, R.; Zanirato, V. Tetrahedron Lett. 1994, 35, 9289–
9292.
9. Dondoni, A.; Perrone, D.; Semola, T. Synthesis 1995,
181–186.
10. Denis, J.-N.; Correa, A.; Greene, A. E. J. Org. Chem.
1991, 56, 6939–6942.
11. Jayasinghe, L. R.; Datta, A.; Ali, S. M.; Zygmunt, J.;
Vander Velde, D. G.; Georg, G. I. J. Med. Chem. 1994,
37, 2981–2984.
4.4.1. Benzoate, 11a. A 3:1 mixture of (1S,2S)-9a and
(1R,2S)-9b (1.025 g, 2.968 mmol) was esterified with
benzoyl chloride as described earlier14 to give crude
product (0.666 g, 83%), which was purified on a silica
gel column followed by crystallisation. The benzoate
(1S,2S)-11a was obtained in 30% yield (0.392 g). Mp
93.0–93.8°C.
4.4.2. Phosphonate (1S,2S)-10a. The benzoate (1S,2S)-
11a (0.130 g, 0.289 mmol) was treated with 3.7 M
HCl–AcOEt as described earlier14 to afford (1S,2S)-10a
(0.082 g, 82%). Mp. 117–118°C. Retention time: tR=
21.92 min.
12. Wro´blewski, A. E.; Piotrowska, D. G. Tetrahedron 1998,
54, 8123–8132.
13. Wro´blewski, A. E.; Piotrowska, D. G. Tetrahedron:
Asymmetry 1999, 10, 2037–2044.
14. Wro´blewski, A. E.; Piotrowska, D. G. Tetrahedron:
Asymmetry 2000, 11, 2615–2624.
15. Kawano, T.; Ogawa, T.; Islam, S. Md.; Ueda, I. Hetero-
cycles 2000, 52, 1279–1295.
16. Alexakis, A.; Lensen, N.; Mangeney, P. Synlett 1991,
625–626.
17. Morita, T.; Nagasawa, Y.; Yahiro, S.; Matsunaga, H.;
Kunieda, T. Org. Lett. 2001, 3, 897–899.
18. Myers, A. G.; Kung, D. W.; Zhong, B. J. Am. Chem.
Soc. 2000, 122, 3236–3237.
19. Myers, A. G.; Zhong, B.; Kung, D. W.; Movassaghi, M.;
Lanman, B. A.; Kwon, S. Org. Lett. 2000, 2, 3337–3340.
20. Myers, A. G.; Zhong, B.; Movassaghi, M.; Kung, D. W.;
Lanman, B. A.; Kwon, S. Tetrahedron Lett. 2000, 41,
1359–1362.
Retention times for the racemic mixture: tR(1R,2R)-
10a=16.73 min, tR(1S,2S)-10a=21.95 min.
4.4.3. Phosphonate (1S,2S)-9a. The benzoate (1S,2S)-
11a (0.075 g. 0.167 mmol) was dissolved in methanol
(0.5 mL) and treated with aqueous ammonia (25%, 1
mL) for 24 h.14 After column chromatography on a
silica gel column, (1S,2S)-9a (0.022g, 40%) was
obtained as a colourless oil. Retention time: tR=8.30
min.
Retention times for the racemic mixture: tR(1R,2R)-
9a=10.04 min, tR(1S,2S)-9a=8.86 min.
21. Chang, Z. Y.; Coats, R. M. J. Org. Chem. 1990, 55,
3464–3474.
Acknowledgements
22. Lewandowicz, A.; Lipin´ski, J.; Siedlecka, R.; Skarz
; ewski,
We thank Mrs. Jolanta Plocka for her skilled experi-
mental contributions. Financial support from the Medi-
cal University of Ło´dz´ (503-311-1) and KBN (7 T09A
121 21) is gratefully acknowledged.
J.; Baert, F. Tetrahedron 1998, 54, 6571–6586.
23. Mancuso, A. J.; Huang, S.-L.; Swern, D. J. Org. Chem.
1978, 43, 2480–2482.
24. Mancuso, A. J.; Swern, D. Synthesis 1981, 165–185.
25. Dess, D. B.; Martin, J. C. J. Org. Chem. 1983, 48,
4155–4156.
26. Dess, D. B.; Martin, J. C. J. Am. Chem. Soc. 1991, 113,
7277–7287.
References
1. Jurczak, J.; Gołe˛biowski, A. Chem. Rev. 1989, 89, 149–
27. Ireland, R. E.; Liu, L. J. Org. Chem. 1993, 58, 2899.
28. Meyer, S. D.; Schreiber, S. L. J. Org. Chem. 1994, 59,
7549–7552.
164.
2. Veeresa, G.; Datta, A. Tetrahedron Lett. 1998, 39, 3069–
3070.
29. Piotrowska, D. G.; Hałajewska-Wosik, A.; Wro´blewski,
A. E. Synth. Commun. 2000, 30, 3935–3940.
3. Veeresa, G.; Datta, A. Tetrahedron Lett. 1998, 39, 119–
3070.