Synthesis of 1-hydroxybicyclo[n.1.0]alkanes (n = 3 and 4) and their silyl ethers from olefinic esters via tandem intramolecular nucleophilic acyl substitution and intramolecular carbonyl addition reactions mediated by Ti(OPr-i)4 / 2 i-PrMgCl reagent

Tetrahedron Letters

Volumn 37, Issue 11, 1996, Pages 1849-1852

  Kasatkin, Aleksandr ^a   Kobayashi, Katsushige ^a   Okamoto, Sentaro ^a   Sato, Fumie ^a  

^a TOKYO INSTITUTE OF TECHNOLOGY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

BICYCLO COMPOUND;

ARTICLE; DRUG SYNTHESIS; REACTION ANALYSIS;

EID: 0029970235     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)00160-8     Document Type: Article

References (26)

1. (a) Murai, S.; Ryu, I.; Sonoda, N. J. Organometal. Chem. 1983, 250, 121.
2. (b) Kuwajima, I.; Nakamura, E. Top. Curr. Chem. 1990, 155, 1.
3. (c) Ito, Y.; Fujii, S; Nakatsuka, M.; Kawamoto, F.; Saegusa, T. Org. Synth. Coll. Vol. 6, 1988, 327.
4. (d) Ryu, I.; Matsumoto, K.; Kameyama, Y.; Ando, M.; Kusumoto, N.; Ogawa, A.; Kambe, N.; Murai, S.; Sonoda, N. J. Am. Chem. Soc. 1993, 115, 12330.
5. (e) Kirihara, M.; Yokoyama, S.; Kakuda, H.; Momose, T. Tetrahedron Lett. 1995, 36, 6907 and references cited therein.
6. 2 by using Zn-Cu couple, see: (a) Le Goaller, R.; Pierre, J.-L. Bull. Soc. Chim. Fr. 1973, 1531.
7. (b) Rubottom, G. M.; Lopez, M. I. J. Org. Chem. 1973, 38, 2097.
8. (c) Murai, S.; Aya, T.; Sonoda, N. J. Org. Chem. 1973, 38, 4354
9. By using Zn-Ag couple, see: (d) Conia, J. M.; Girard, C. Tetrahedron Lett. 1973, 2767.
10. (e) Girard, C.; Conia, J. M. Tetrahedron Lett. 1974, 3327.
11. 2Zn, see: (f) Ryu, I.; Murai, S.; Sonoda, N Tetrahedron Lett. 1977, 4611.
12. (g) Miyano, S.; Izumi, Y.; Fujii, H.; Hashimoto, H. Synthesis 1977, 700.
13. 2 has been also reported, see: Imamoto, T.; Takiyama, N. Tetrahedron Lett. 1987, 28, 1307.
14. For regioselective synthesis of enol silyl ethers from various ketones under conditions of either kinetic or thermodynamic control, see reviews: Rasmussen, J. K. Synthesis 1977, 91. Brownbridge, P. Synthesis 1983, 1 and 85. Taylor, R. J. K. Synthesis 1985, 364.
15. For regioselective synthesis of enol silyl ethers from various ketones under conditions of either kinetic or thermodynamic control, see reviews: Rasmussen, J. K. Synthesis 1977, 91. Brownbridge, P. Synthesis 1983, 1 and 85. Taylor, R. J. K. Synthesis 1985, 364.
16. For regioselective synthesis of enol silyl ethers from various ketones under conditions of either kinetic or thermodynamic control, see reviews: Rasmussen, J. K. Synthesis 1977, 91. Brownbridge, P. Synthesis 1983, 1 and 85. Taylor, R. J. K. Synthesis 1985, 364.
17. (a) Kasatkin, A.; Nakagawa, T.; Okamoto, S.; Sato, F. J. Am. Chem. Soc. 1995, 117, 3881.
18. (b) Kasatkin, A.; Okamoto, S.; Sato, F. Tetrahedron Lett. 1995, 36, 6075.
19. (c) Kasatkin, A.; Sato, F. Tetrahedron Lett. 1995, 36, 6079, see also references cited therein.
20. Oxidation of 1-hydroxybicyclo[n.1.0]alkanes 3 or their silyl ethers 4 to ω-alkenoic acids 2 (R = H) was reported; Rubottom, G. M.; Marrero, R.; Krueger, D. S.; Schreiner, J. L. Tetrahedron Lett. 1977, 4013. Rubottom, G. M.; Beedle, E. C.; Kim, C.-W.; Mott, R. C. J. Am. Chem. Soc. 1985, 707, 4230. See also ref. 2e.
21. Oxidation of 1-hydroxybicyclo[n.1.0]alkanes 3 or their silyl ethers 4 to ω-alkenoic acids 2 (R = H) was reported; Rubottom, G. M.; Marrero, R.; Krueger, D. S.; Schreiner, J. L. Tetrahedron Lett. 1977, 4013. Rubottom, G. M.; Beedle, E. C.; Kim, C.-W.; Mott, R. C. J. Am. Chem. Soc. 1985, 707, 4230. See also ref. 2e.
22. 4, and concentrated in vacuo. The crude product was purified by column chromatography on silica gel (Wako C-200, hexane / AcOEt, 5: 1) to give 1-hydroxy-2-benzylbicyclo[3.1.0]hexane (3a) (0.145 g, 77% yield) as a mixture (66 : 34) of diastereomers.
23. Klebe, J. F.; Finkbeiner, H.; White, D. M. J. Am. Chem. Soc. 1966, 88, 3390.
24. Substituted 1-hydroxybicyclo[n.1.0]alkanes of the type 3e (entry 6) were prepared according to the following scheme; see, for example: Iwasawa, N.; Funahashi, M.; Hayakawa, S.; Narasaka, K. Chem. Lett. 1993, 545. Booker-Milburn, K. I. Synlett, 1992, 809. (matrix presented)
25. Substituted 1-hydroxybicyclo[n.1.0]alkanes of the type 3e (entry 6) were prepared according to the following scheme; see, for example: Iwasawa, N.; Funahashi, M.; Hayakawa, S.; Narasaka, K. Chem. Lett. 1993, 545. Booker-Milburn, K. I. Synlett, 1992, 809. (matrix presented)
26. Complicated mixtures of unidentified products along with 20-30% of the starting materials were isolated in both reactions.