Stereochemical research on the hydrolysis of optically pure spirosulfuranes: Efficient synthesis of chiral sulfoxides with completely opposite stereochemistry

Journal of Organic Chemistry

Volumn 63, Issue 25, 1998, Pages 9375-9384

  Zhang, Jian ^a   Saito, Shinichi ^a   Koizumi, Toru ^a  

^a UNIVERSITY OF TOKYO   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

SPIROSULFURANE; SULFOXIDE; SULFUR DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHIRALITY; CRYSTAL STRUCTURE; CRYSTALLIZATION; CYCLIZATION; DIASTEREOISOMER; DISSOCIATION; HYDROLYSIS; ISOTOPE LABELING; MASS SPECTROMETRY; NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; STEREOCHEMISTRY; STRUCTURE ANALYSIS; SYNTHESIS; X RAY CRYSTALLOGRAPHY;

EID: 0032509529     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo981330t     Document Type: Article

References (79)

1. Reviews on the reactions of the pentacoordinated silicon and phosphorus compounds: (a) Holmes, R. R. Acc. Chem. Res. 1972, 5, 296-303. (b) Holmes, R. R. Acc. Chem. Res. 1979, 12, 257-265. (c) Chuit, C.; Corriu, R. J. P.; Reye, C.; Young, J. C. Chem. Rev. 1993, 93, 1371-1448. (d) Dillon, K. B. Chem. Rev. 1994, 94, 1441-1456. (e) Holmes, R. R. Chem. Rev. 1996, 96, 927-950. Recent example: (f) Chang, N.; Lim, C. J. Am. Chem. Soc. 1998, 120, 2156-2167.
2. Reviews on the reactions of the pentacoordinated silicon and phosphorus compounds: (a) Holmes, R. R. Acc. Chem. Res. 1972, 5, 296-303. (b) Holmes, R. R. Acc. Chem. Res. 1979, 12, 257-265. (c) Chuit, C.; Corriu, R. J. P.; Reye, C.; Young, J. C. Chem. Rev. 1993, 93, 1371-1448. (d) Dillon, K. B. Chem. Rev. 1994, 94, 1441-1456. (e) Holmes, R. R. Chem. Rev. 1996, 96, 927-950. Recent example: (f) Chang, N.; Lim, C. J. Am. Chem. Soc. 1998, 120, 2156-2167.
3. Reviews on the reactions of the pentacoordinated silicon and phosphorus compounds: (a) Holmes, R. R. Acc. Chem. Res. 1972, 5, 296-303. (b) Holmes, R. R. Acc. Chem. Res. 1979, 12, 257-265. (c) Chuit, C.; Corriu, R. J. P.; Reye, C.; Young, J. C. Chem. Rev. 1993, 93, 1371-1448. (d) Dillon, K. B. Chem. Rev. 1994, 94, 1441-1456. (e) Holmes, R. R. Chem. Rev. 1996, 96, 927-950. Recent example: (f) Chang, N.; Lim, C. J. Am. Chem. Soc. 1998, 120, 2156-2167.
4. Reviews on the reactions of the pentacoordinated silicon and phosphorus compounds: (a) Holmes, R. R. Acc. Chem. Res. 1972, 5, 296-303. (b) Holmes, R. R. Acc. Chem. Res. 1979, 12, 257-265. (c) Chuit, C.; Corriu, R. J. P.; Reye, C.; Young, J. C. Chem. Rev. 1993, 93, 1371-1448. (d) Dillon, K. B. Chem. Rev. 1994, 94, 1441-1456. (e) Holmes, R. R. Chem. Rev. 1996, 96, 927-950. Recent example: (f) Chang, N.; Lim, C. J. Am. Chem. Soc. 1998, 120, 2156-2167.
5. Reviews on the reactions of the pentacoordinated silicon and phosphorus compounds: (a) Holmes, R. R. Acc. Chem. Res. 1972, 5, 296-303. (b) Holmes, R. R. Acc. Chem. Res. 1979, 12, 257-265. (c) Chuit, C.; Corriu, R. J. P.; Reye, C.; Young, J. C. Chem. Rev. 1993, 93, 1371-1448. (d) Dillon, K. B. Chem. Rev. 1994, 94, 1441-1456. (e) Holmes, R. R. Chem. Rev. 1996, 96, 927-950. Recent example: (f) Chang, N.; Lim, C. J. Am. Chem. Soc. 1998, 120, 2156-2167.
6. Reviews on the reactions of the pentacoordinated silicon and phosphorus compounds: (a) Holmes, R. R. Acc. Chem. Res. 1972, 5, 296-303. (b) Holmes, R. R. Acc. Chem. Res. 1979, 12, 257-265. (c) Chuit, C.; Corriu, R. J. P.; Reye, C.; Young, J. C. Chem. Rev. 1993, 93, 1371-1448. (d) Dillon, K. B. Chem. Rev. 1994, 94, 1441-1456. (e) Holmes, R. R. Chem. Rev. 1996, 96, 927-950. Recent example: (f) Chang, N.; Lim, C. J. Am. Chem. Soc. 1998, 120, 2156-2167.
7. (g) Kubo, K.; Nakazawa, H.; Kawamura, K.; Mizuta, T.; Miyoshi, K. J. Am. Chem. Soc. 1998, 120, 6715-6727.
8. Reviews on the chemistry of chalcogenuranes: (a) Martin, J. C.; Paul, I. C. Science 1976, 191, 154-159. (b) Martin, J. C. Science 1983, 221, 509-514. (c) Hayes, R. A.; Martin, J. C. In Organic Sulfur Chemistry, Theoretical and Experimental Advances; Bernardi, F., Csizmadia, I. G., Mangini, A., Eds.; Elsevier: Amsterdam, 1985; pp 408-483. (d) Oae, S. Organic Sulfur Chemistry: Structure and Mechanism; CRC Press: Boca Raton, FL, 1991.
9. Reviews on the chemistry of chalcogenuranes: (a) Martin, J. C.; Paul, I. C. Science 1976, 191, 154-159. (b) Martin, J. C. Science 1983, 221, 509-514. (c) Hayes, R. A.; Martin, J. C. In Organic Sulfur Chemistry, Theoretical and Experimental Advances; Bernardi, F., Csizmadia, I. G., Mangini, A., Eds.; Elsevier: Amsterdam, 1985; pp 408-483. (d) Oae, S. Organic Sulfur Chemistry: Structure and Mechanism; CRC Press: Boca Raton, FL, 1991.
10. Reviews on the chemistry of chalcogenuranes: (a) Martin, J. C.; Paul, I. C. Science 1976, 191, 154-159. (b) Martin, J. C. Science 1983, 221, 509-514. (c) Hayes, R. A.; Martin, J. C. In Organic Sulfur Chemistry, Theoretical and Experimental Advances; Bernardi, F., Csizmadia, I. G., Mangini, A., Eds.; Elsevier: Amsterdam, 1985; pp 408-483. (d) Oae, S. Organic Sulfur Chemistry: Structure and Mechanism; CRC Press: Boca Raton, FL, 1991.
11. Reviews on the chemistry of chalcogenuranes: (a) Martin, J. C.; Paul, I. C. Science 1976, 191, 154-159. (b) Martin, J. C. Science 1983, 221, 509-514. (c) Hayes, R. A.; Martin, J. C. In Organic Sulfur Chemistry, Theoretical and Experimental Advances; Bernardi, F., Csizmadia, I. G., Mangini, A., Eds.; Elsevier: Amsterdam, 1985; pp 408-483. (d) Oae, S. Organic Sulfur Chemistry: Structure and Mechanism; CRC Press: Boca Raton, FL, 1991.
12. Recent reviews on the reactions concerning the formation of chalcogenuranes as intermediates: (a) Mancuso, A. J.; Swern, D. Synthesis 1981, 164-185. (b) Tidwell, T. T. Synthesis 1990, 857-870. (c) Oae, S.; Uchida, Y. Acc. Chem. Res. 1991, 24, 202-208. (d) Kita, Y. Phosphorus, Sulfur Silicon 1997, 120 and 121, 145-164. (e) Kawashima, T.; Okazaki, R. Synlett 1996, 600-608.
13. Recent reviews on the reactions concerning the formation of chalcogenuranes as intermediates: (a) Mancuso, A. J.; Swern, D. Synthesis 1981, 164-185. (b) Tidwell, T. T. Synthesis 1990, 857-870. (c) Oae, S.; Uchida, Y. Acc. Chem. Res. 1991, 24, 202-208. (d) Kita, Y. Phosphorus, Sulfur Silicon 1997, 120 and 121, 145-164. (e) Kawashima, T.; Okazaki, R. Synlett 1996, 600-608.
14. Recent reviews on the reactions concerning the formation of chalcogenuranes as intermediates: (a) Mancuso, A. J.; Swern, D. Synthesis 1981, 164-185. (b) Tidwell, T. T. Synthesis 1990, 857-870. (c) Oae, S.; Uchida, Y. Acc. Chem. Res. 1991, 24, 202-208. (d) Kita, Y. Phosphorus, Sulfur Silicon 1997, 120 and 121, 145-164. (e) Kawashima, T.; Okazaki, R. Synlett 1996, 600-608.
15. Recent reviews on the reactions concerning the formation of chalcogenuranes as intermediates: (a) Mancuso, A. J.; Swern, D. Synthesis 1981, 164-185. (b) Tidwell, T. T. Synthesis 1990, 857-870. (c) Oae, S.; Uchida, Y. Acc. Chem. Res. 1991, 24, 202-208. (d) Kita, Y. Phosphorus, Sulfur Silicon 1997, 120 and 121, 145-164. (e) Kawashima, T.; Okazaki, R. Synlett 1996, 600-608.
16. Recent reviews on the reactions concerning the formation of chalcogenuranes as intermediates: (a) Mancuso, A. J.; Swern, D. Synthesis 1981, 164-185. (b) Tidwell, T. T. Synthesis 1990, 857-870. (c) Oae, S.; Uchida, Y. Acc. Chem. Res. 1991, 24, 202-208. (d) Kita, Y. Phosphorus, Sulfur Silicon 1997, 120 and 121, 145-164. (e) Kawashima, T.; Okazaki, R. Synlett 1996, 600-608.
17. (a) House, K. L.; Dunlap, R. B.; Odom, J. D.; Wu, Z.-P.; Hilvert, D. J. Am. Chem. Soc. 1992, 114, 8573-8579.
18. (b) Engman, L.; Stern, D.; Cotgreave, I. A.; Andersson, C. M. J. Am. Chem. Soc. 1992, 114, 9737-9743.
19. (c) Engman, L.; Stern, D.; Pelcman, M.; Andersson, C. M. J. Org. Chem. 1994, 59, 1973-1979.
20. (d) Detty, M. R.; Friedman, A. E.; Oseroff, A. R. J. Org. Chem. 1994, 59, 8245-8250.
21. (e) Iwaoka, M.; Tomoda, S. J. Am. Chem. Soc. 1994, 116, 2557-2561.
22. (f) Vessman, K.; Ekström, M.; Berglund, M.; Andersson, C. M.; Engman, L. J. Org. Chem. 1995, 60, 4461-4467.
23. (g) Mohsine, A.; Christiaens, L. Heterocycles 1996, 43, 2567-2593.
24. (h) Back, T. G.; Dyck, B. P, J. Am. Chem. Soc. 1997, 119, 2079-2083.
25. (i) Fong, M. C.; Schiesser, C. H. J. Org. Chem. 1997, 62, 3103-3108.
26. (j) Detty, M. R.; Zhou, F.; Friedman, A. E. J. Am. Chem. Soc. 1996, 118, 313-318.
27. (k) Albeck, A.; Weitman, H.; Sredni, B.; Albeck, M. Inorg. Chem. 1998, 37, 1704-1712.
28. (a) Balthazor, T. M.; Martin, J. C. J. Am. Chem. Soc. 1975, 97, 5634-5635.
29. (b) Martin, J. C.; Balthazor, T. M. J. Am. Chem. Soc. 1977, 99, 152-162.
30. On the synthesis and isolation of chiral spirosulfuranes: (a) Huszthy, P.; Kapovits, I.; Kucsman, Á.; Radics, L. Tetrahedron Lett. 1978, 1853-1856. (b) Allenmark, S.; Claeson, S. Tetrahedron: Asymmetry 1993, 4, 2329-2332. (c) Drabowicz, J.; Martin, J. C. Tetrahedron: Asymmetry 1993, 4, 297-300. (d) Drabowicz, J.; Martin, J. C. Pure Appl. Chem. 1996, 68, 951-956. (e) Szabó, D.; Szendeffy, S.; Kapovits, I.; Kucsman, Á.; Czugler, M.; Kálmán, A.; Nagy, P. Tetrahedron: Asymmetry 1997, 8, 2411-2420.
31. On the synthesis and isolation of chiral spirosulfuranes: (a) Huszthy, P.; Kapovits, I.; Kucsman, Á.; Radics, L. Tetrahedron Lett. 1978, 1853-1856. (b) Allenmark, S.; Claeson, S. Tetrahedron: Asymmetry 1993, 4, 2329-2332. (c) Drabowicz, J.; Martin, J. C. Tetrahedron: Asymmetry 1993, 4, 297-300. (d) Drabowicz, J.; Martin, J. C. Pure Appl. Chem. 1996, 68, 951-956. (e) Szabó, D.; Szendeffy, S.; Kapovits, I.; Kucsman, Á.; Czugler, M.; Kálmán, A.; Nagy, P. Tetrahedron: Asymmetry 1997, 8, 2411-2420.
32. On the synthesis and isolation of chiral spirosulfuranes: (a) Huszthy, P.; Kapovits, I.; Kucsman, Á.; Radics, L. Tetrahedron Lett. 1978, 1853-1856. (b) Allenmark, S.; Claeson, S. Tetrahedron: Asymmetry 1993, 4, 2329-2332. (c) Drabowicz, J.; Martin, J. C. Tetrahedron: Asymmetry 1993, 4, 297-300. (d) Drabowicz, J.; Martin, J. C. Pure Appl. Chem. 1996, 68, 951-956. (e) Szabó, D.; Szendeffy, S.; Kapovits, I.; Kucsman, Á.; Czugler, M.; Kálmán, A.; Nagy, P. Tetrahedron: Asymmetry 1997, 8, 2411-2420.
33. On the synthesis and isolation of chiral spirosulfuranes: (a) Huszthy, P.; Kapovits, I.; Kucsman, Á.; Radics, L. Tetrahedron Lett. 1978, 1853-1856. (b) Allenmark, S.; Claeson, S. Tetrahedron: Asymmetry 1993, 4, 2329-2332. (c) Drabowicz, J.; Martin, J. C. Tetrahedron: Asymmetry 1993, 4, 297-300. (d) Drabowicz, J.; Martin, J. C. Pure Appl. Chem. 1996, 68, 951-956. (e) Szabó, D.; Szendeffy, S.; Kapovits, I.; Kucsman, Á.; Czugler, M.; Kálmán, A.; Nagy, P. Tetrahedron: Asymmetry 1997, 8, 2411-2420.
34. On the synthesis and isolation of chiral spirosulfuranes: (a) Huszthy, P.; Kapovits, I.; Kucsman, Á.; Radics, L. Tetrahedron Lett. 1978, 1853-1856. (b) Allenmark, S.; Claeson, S. Tetrahedron: Asymmetry 1993, 4, 2329-2332. (c) Drabowicz, J.; Martin, J. C. Tetrahedron: Asymmetry 1993, 4, 297-300. (d) Drabowicz, J.; Martin, J. C. Pure Appl. Chem. 1996, 68, 951-956. (e) Szabó, D.; Szendeffy, S.; Kapovits, I.; Kucsman, Á.; Czugler, M.; Kálmán, A.; Nagy, P. Tetrahedron: Asymmetry 1997, 8, 2411-2420.
35. (a) Takahashi, T.; Kurose, N.; Kawanami, S.; Arai, Y.; Koizumi, T.; Shiro, M. J. Org. Chem. 1994, 59, 3262-3264.
36. (b) Takahashi, T.; Kurose, N.; Kawanami, S.; Nojiro, A.; Arai, Y.; Koizumi, T.; Shiro, M. Chem. Lett. 1995, 379-380.
37. (c) Kurose, N.; Takahashi, T.; Koizumi, T. J. Org. Chem. 1996, 61, 2932-2933.
38. (d) Takahashi, T.; Zhang, J.; Kurose, N.; Takahashi, S.; Koizumi, T.; Shiro, M. Tetrahedron: Asymmetry 1996, 7, 2797-2800.
39. (e) Zhang, J.; Takahashi, T.; Koizumi, T. Heterocycles 1997, 44, 325-339.
40. (f) Kurose, N.; Takahashi, T.; Koizumi, T. J. Org. Chem. 1997, 62, 4562-4563.
41. (g) Kurose, N.; Takahashi, T.; Koizumi, T. Tetrahedron 1997, 53, 12115-12129.
42. (h) Zhang, J.; Saito, S.; Koizumi, T. Tetrahedron: Asymmetry 1997, 8, 3357-3361.
43. (i) Zhang, J.; Saito, S.; Koizumi, T. J. Org. Chem. 1998, 63, 5265-5267.
44. (j) Zhang, J.; Saito, S.; Koizumi, T. J. Org. Chem. 1998, 63, 5423-5429.
45. (a) Koizumi, T. Phosphorus, Sulfur Silicon 1991, 58, 111-127.
46. (b) Arai, Y. Koizumi, T. Sulfur Rep. 1993, 15, 41-65.
47. (c) Aversa, M. C.; Barattucci, A.; Bonaccorsi, P.; Giannetto, P.; Panzalorto, M.; Rizzo, S. Tetrahedron: Asymmetry 1998, 9, 1577-1588, and references therein.
48. (d) Takahashi, T.; Nakao, N.; Koizumi, T. Chem. Lett. 1996, 207-208.
49. (e) Takahashi, T.; Nakao, N.; Koizumi, T. Tetrahedron: Asymmetry 1997, 8, 3293-3308.
50. Preliminary communication of this work: Zhang, J.; Saito, S.; Koizumi, T. J. Am. Chem. Soc. 1998, 120, 1631-1632.
51. 1H NMR analysis of the crude product which was directly evaporated without extraction.
52. Livant, P.; Martin, J. C. J. Am. Chem. Soc. 1977, 99, 5761-5767.
53. (a) Adzima, L. J.; Martin, J. C. J. Org. Chem. 1977, 42, 4006-4016.
54. (b) Kapovits, I.; Rábai, J.; Szabó, D.; Czakó, K.; Kucsman, Á.; Argay, G.; Fülöp, V.; Kálmán, A.; Koritsánszky, T.; Párkányi, L. J. Chem. Soc., Perkin Trans. 2 1993, 847-853.
55. (c) Hornbuckle, S. F.; Livant, P.; Webb, T. R. J. Org. Chem. 1995, 60, 4153-4159.
56. (d) Szabó, D.; Kapovits, I.; Argay, G.; Czugler, M.; Kálmán, A.; Koritsánszky, T. J. Chem. Soc., Perkin Trans. 2 1997, 1045-1053.
57. (a) Lam, W. Y.; Duesler, E. N.; Martin, J. C. J. Am Chem. Soc. 1981, 103, 127-135.
58. (b) Vass, E.; Ruff, F.; Kapovits, I.; Rábai, J.; Szabó, D. J. Chem. Soc., Perkin Trans. 2 1993, 855-859.
59. (c) Vass, E.; Ruff, F.; Kapovits, I.; Szabó, D.; Kucsman, Á. J. Chem. Soc., Perkin Trans. 2 1997, 2061-2068.
60. (d) Adám, T.; Ruff, F.; Kapovits, I.; Szabó, D.; Kucsman, Á. J. Chem. Soc., Perkin Trans. 2 1998, 1269-1275.
61. (a) Lucchi, O. D.; Lucchini, V.; Marchioro, L.; Valle, G.; Modena, G. J. Org. Chem. 1986, 51, 1457-1466. Lucchi, O. D.; Lucchini, V.; Marchioro, L.; Valle, G.; Modena, G. J. Org. Chem. 1989, 54, 3245.
62. (a) Lucchi, O. D.; Lucchini, V.; Marchioro, L.; Valle, G.; Modena, G. J. Org. Chem. 1986, 51, 1457-1466. Lucchi, O. D.; Lucchini, V.; Marchioro, L.; Valle, G.; Modena, G. J. Org. Chem. 1989, 54, 3245.
63. (b) Annunziata, R.; Cinquini, M.; Cozzi, F.; Farina, S.; Montanari, V. Tetrahedron 1987, 43, 1013-1018.
64. (c) Eschler, B. M.; Haynes, R. K.; Kremmydas, S.; Ridley, D. D. J. Chem. Soc., Chem. Commun. 1988, 137-138.
65. (d) Hung, S. M.; Lee, D. S.; Yang, T. K. Tetrahedron: Asymmetry 1990, 1, 873-876.
66. (e) Arai, Y.; Matsui, M.; Koizumi, T. Synthesis 1990, 320-323.
67. (f) Eschler, B. M.; Haynes, R. K.; Ironside, M. D.; Kremmydas, S.; Ridley, D. D.; Hambley, T. W. J. Org. Chem. 1991, 56, 4760-4766.
68. To confirm the stereochemistry of 8c,d, hydrolysis of chlorosulfuranes 6c,d under basic condition has been performed to give sulfoxides in high yield and diastereoselectivity. The spectral data of the products are identical with that of sulfoxides 8c,d, which indicated definitely that the stereochemistry of the sulfoxides are as shown in Scheme 3.
69. (a) Shimizu, T.; Yoshida, M.; Kobayashi, M. Bull. Chem. Soc., Jpn. 1987, 60, 1555-1557.
70. (b) Shimizu, T.; Kobayashi, M.; Kamigata, N. Bull. Chem. Soc., Jpn. 1988, 61, 3761-3763.
71. (c) Shimizu, T.; Kamigata, N. J. Synth. Org. Chem., Jpn. 1997, 55, 35-43.
72. 16O) there are no peaks at m/z = 186.
73. 17O NMR spectroscope, see: (b) Dyer, J. C.; Harris, D. C.; Evans, J. S. A. J. Org. Chem. 1982, 47, 3660-3664.
74. 17O NMR spectroscope, see: (b) Dyer, J. C.; Harris, D. C.; Evans, J. S. A. J. Org. Chem. 1982, 47, 3660-3664.
75. Twenty years ago, Martin et al. studied the mechanism of the basic hydrolysis of chlorosulfuranes and proposed an associative mechanism involving a hexacoordinated sulfur species with a negative charge on sulfur, see: ref 5.
76. BH+ = -6.5). March, J. Advanced Organic Chemistry: Reactions, Mechanisms, and Structure; Wiley-Interscience: New York, 1992; p 250. Since the lack of the precise data of the basicity of the two S-O groups in the alkoxy(acyloxy)spirosulfuranes, we think data cited herein is reasonable to support the order of the protonation of the two S-O groups proposed. Considering the central sulfur as a carbon atom, the basicity of the two oxygens in the structure of C-O-S-O-C(=O) should have similar order as that of C-O-C-O-C(= O). However, the two oxygen atoms might influence each other through the hypervalent O-S-O bond system, which might be different from that of the O-C-O system. Further investigation of the reactions using the computer calculation is ongoing, and the results will be reported elsewhere.
77. The pentacoordinated intermediates (C and E) can be reasonably considered as with the TBP geometry, and the most electronegative groups in C and E are expected to occupy axial positions.
78. The S-O (acyloxy) bond is expected to hydrolyze easier compared with the S-O (alkoxy) bond in alkoxy(acyloxy)spirosulfuranes since the S-O (acyloxy) bond is longer and more negative charge is distributed on the S-O (acyloxy) bond than S-O (alkoxy), see: ref 13a.
79. Yamakoshi, Y. N.; Ge, W. Y.; Okayama, K.; Takahashi, T.; Koizumi, T. Heterocycles 1996, 42, 129-133.