1,5-Benzodithiepan-3-one 1,5-dioxide: A novel chiral auxiliary for asymmetric desymmetrization of meso-1,2-diols

Tetrahedron Asymmetry

Volumn 7, Issue 10, 1996, Pages 2787-2790

  Maezaki, Naoyoshi ^a   Sakamoto, Atsunobu ^a   Soejima, Motohiro ^a   Sakamoto, Ikuyo ^a   Xia, Li Ying ^a   Tanaka, Tetsuaki ^a   Ohishi, Hirofumi ^b   Sakaguchi, Ken Ichi ^a   Iwata, Chuzo ^a  

^a OSAKA UNIVERSITY   (Japan)

^b OSAKA MEDICAL COLLEGE   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALKANEDIOL DERIVATIVE; CYCLOALKANOL DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; PRIORITY JOURNAL; REACTION ANALYSIS; STEREOCHEMISTRY; TECHNIQUE;

EID: 0030272678     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/0957-4166(96)00362-X     Document Type: Article

References (29)

1. 1. Reviews for enzymatic asymmetric desymmetrization, Schoffers, E.; Golebiowski, A.; Johnson, C. R. Tetrahedron 1996, 52, 3769-3826 and references cited therein.
2. 2. For chemical asymmetric desymmetrization using sulfoxide as a chiral auxiliary, see: (a) Maezaki, N.; Soejima, M.; Takeda, M.; Sakamoto, A.; Matsumori, Y.; TanakaT.; Iwata, C. Tetrahedron, 1996, 52, 6527-6546.
3. (b) Maezaki, N.; Murakami, M; Soejima, M.; Tanaka, T.; Imanishi, T.; Iwata, C. Chem. Pharm. Bull., 1996, 44, 1146-1151.
4. (c) Maezaki, N.; Soejima, M.; Sakamoto, A.; Sakamoto, I.; Matsumori, Y.; Tanaka, T.; Ishida, T.; In, Y.; Iwata, C. Tetrahedron : Asymmetry 1996, 7, 29-32.
5. (d) Maezaki, N.; Soejima, M.; Takeda, M.; Sakamoto, A.; Tanaka, T.; Iwata, C. J. Chem. Soc., Chem. Commun. 1994, 1345-1346.
6. (e) Iwata, C.; Maezaki, N.; Hattori, K.; Fujita, M.; Moritani, Y.; Takemoto, Y.; Tanaka, T.; Imanishi, T. Chem. Pharm. Bull. 1993, 41, 339-345.
7. (f) Iwata, C.; Maezaki, N.; Hattori, K.; Fujita, M.; Moritani, Y.; Takemoto, Y.; Tanaka, T.; Imanishi, T. Chem. Pharm. Bull. 1993, 41, 946-950.
8. (g) Iwata, C.; Maezaki, N.; Murakami, M.; Soejima, M.; Tanaka, T.; Imanishi, T. J. Chem. Soc., Chem. Commun. 1992, 516-518.
9. (h) Iwata, C.; Fujita, M.; Moritani. Y.; Sugiyama, K.; Hattori, K.; Imanishi, T. Tetrahedron Lett. 1987, 28, 3131-3134.
10. (i) Iwata, C.; Fujita, M.; Moritani, Y.; Hattori, K.; Imanishi, T. Tetrahedron Lett. 1987, 28, 3135-3138.
11. 3. For chemical asymmetric desymmetrization using trans-1,2-cyclohexanediol as a chiral auxiliary, see; (a) Sakai, K.; Suemune, H. Tetrahedron: Asymmetry 1993, 4, 2109-2118.
12. (b) Suemune, H.; Watanabe, K.; Kato, K.; Sakai, K. Tetrahedron: Asymmetry 1993, 4, 1767-1770.
13. 4. For chemical asymmetric desymmetrization using menthone as a chiral auxiliary, see: (a) Harada, T.; Oku, A. Synlett 1994, 95-104.
14. (b) Harada, T.; Wada, I.; Oku, A. J. Org. Chem. 1989, 54, 2599-2605.
15. (c) Harada, T.; Sakamoto, K.; Ikemura, Y.; Oku, A, Tetrahedron Lett. 1988, 29, 3097-3100.
16. (d) Harada, T.; Hayashiya, T.; Wada, I.; Iwa-ake, N.; Oku, A. J. Am. Chem. Soc. 1987, 109, 527-532.
17. (e) Harada, T.; Wada, I.; Oku, A. Tetrahedron Lett. 1987, 28, 4181-4184.
18. 5. Giolando, D. M.; Kirschbaum, K. Synthesis 1992, 451-452.
19. 6. Tsunoda, T.; Suzuki, M.; Noyori, R. Tetrahedron Lett. 1980, 21, 1357-1358.
20. 7. The products were separated by column chromatography on silica gel (2a and 2b: hexane-AcOEt = 1 : 1, 1, 3 and meso. AcOEt).
21. 8. Cohen, Z.; Keinan, E.; Mazur, Y.; Varkony, T. H. J. Org. Chem. 1975, 40, 2141; Keinan, E.; Mazur, Y. Synthesis 1976, 523.
22. 8. Cohen, Z.; Keinan, E.; Mazur, Y.; Varkony, T. H. J. Org. Chem. 1975, 40, 2141; Keinan, E.; Mazur, Y. Synthesis 1976, 523.
23. 9. Friedel pair reflections and anomalous scatterings were used to determine the absolute configuration.
24. 10. Matsuda, F.; Terashima, S. Tetrahedron 1988, 44, 4721-4736.
25. 4Cl aqueous solution. The work-up was essential to prevent undesirable recyclization of the product. The partially acetylated product was filtrated through a short pad of silica gel and then completely acetylated with acetic anhydride and DMAP.
26. 12. The absolute configurations of the cleaved alcohols 6a and 6b were determined by Mosher's method after conversion into the corresponding MTPA esters; Dale, J. A.; Mosher, H. S. J. Am. Chem. Soc. 1973, 95, 512-519; Idem. J. Org. Chem. 1969, 34, 2543-2549.
27. 12. The absolute configurations of the cleaved alcohols 6a and 6b were determined by Mosher's method after conversion into the corresponding MTPA esters; Dale, J. A.; Mosher, H. S. J. Am. Chem. Soc. 1973, 95, 512-519; Idem. J. Org. Chem. 1969, 34, 2543-2549.
28. 13. The chiral auxiliary (-)-1 was recovered in 95% chemical yield without decreasing the enantiomeric excess (>98% e.e.).
29. 14. By the same procedure as in the case of chiral 5a, racemic 5a was synthesized from the racemic 3, which was prepared by oxidation of 1,5-benzodithiepan-3-one with MCPBA.