A Novel Reducing System for Acetal Cleavage: BH3·S(CH3)2-BF 3·O(C2H5)2 Combination

Synlett

Volumn 1996, Issue 3, 1996, Pages 231-233

  Saito, Seiki ^a   Kuroda, Akiyoshi ^a   Tanaka, Kazuya ^a   Kimura, Ryoichi ^a  

^a OKAYAMA UNIVERSITY   (Japan)

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Indexed keywords

EID: 0000620660     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1996-5397     Document Type: Article

References (20)

1. Saito, S.; Hasegawa, T.; Inaba, M.; Nishida, R.; Fujii, T.; Nomizu, S.; Moriwake, T. Chem. Lett. 1984, 1389.
2. Saito, S.; Ishikawa, T.; Kuroda, A.; Koga, K.; Moriwake, T.; Tetrahedron 1992, 48, 4067.
3. Reetz, M. T.; Kesseler, K. J. Org. Chem. 1985, 50, 5434.
4. For instance, see Fujita, K.; Nakai, H.; Kobayashi, S.; Inoue, K.; Nojima, S.; Ohno, M. Tetrahedron Lett. 1982, 23, 3507.
5. 4/THF/-78 - -20°C) and mono-O-silylation (NaH/TBDMS-Cl/THF/0°C - rt).
6. Eliel, E. L.; Badding, V. C.; Rerick, M. N. J. Am. Chem. Soc. 1962, 84, 2371.
7. Bonner, T. C.; Lewis, D.; Rutter, K. J. Chem. Soc. Perkin 1, 1981, 1807.
8. (a) Takano, S.; Akiyama, M.; Sato, S.; Ogasawara, K. Chem. Lett. 1983, 1593;
9. (b) Takano, S.; Kurotaki, A.; Sekiguchi, Y.; Satoh, S.; Hirama, M.; Ogasawara, K. Synthesis, 1986, 811.
10. (c) Mori, A.; Fujiwara, J.; Maruoka, K.; Yamamoto, H. Tetrahedron Lett. 1983, 24, 4581.
11. (a) Fleming, B.; Bolker, H. I. Can. J. Chem. 1974, 52, 888.
12. 2 with TMSOTf, see Bartels, B.; Hunter, R. J. Org. Chem. 1993, 58, 6756.
13. Borders, R. J.; Bryson, T. A. Chem. Lett. 1984, 9.
14. Davis, H. A.; Brown, R. K. Can. J. Chem. 1971, 492, 2166.
15. For hydroxy-directed acetal cleavage with DIBAH, see ref 8a - b.
16. 2, see Corey, E. J.; Weigel, L. O.; Floyd, D.; Bock, M. G. J. Am. Chem. Soc. 1978, 100, 2916.
17. 3) δ 0.06 (s, 6H), 0.89 (s, 9H), 3.88 (td, J = 1.5, 4.9Hz, 1H), 3.92 (dd, J = 5.0, 10.7 Hz, 1H), 3.95 (dd, J = 4.9, 10.7 Hz, 1H), 4.72 (ABq, 2H), 7.3-7.4 (m, 5H), 9.72 (d, J = 1.5 Hz, 1H).
18. Yields based on the corresponding diacetates which were derived directly from the reaction mixture on treatment with acetic anhydride and triethylamine prior to usual aqueous workup.
19. 3. The resulting mixture was concentrated under reduced pressure (suction max) to give an oil, which, on column chromatography, led to 20 in the indicated yield.
20. 11B-NMR experiments.