Solid phase approach to muscone synthesis: Rh(I)-catalyzed hydroformylation of a 1,1-disubstituted alkene on the Multipin® system

Tetrahedron Letters

Volumn 39, Issue 11, 1998, Pages 1369-1372

  Takahashi, Takashi ^a   Ebata, Satoshi ^a   Doi, Takayuki ^a  

^a TOKYO INSTITUTE OF TECHNOLOGY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE; CROWN ETHER; ETHINYLESTRADIOL PLUS NORETHISTERONE; MUSCONE; POLYMER;

ARTICLE; CHEMICAL REACTION; SOLID; SYNTHESIS;

EID: 0032510298     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)10847-4     Document Type: Article

References (22)

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3. 2. Reviews for solid-phase organic reactions, see: James, I. W.: A Compendium of Solid-Phase Chemistry Publications. In Annual Reports in Combìnatorial Chemistry and Molecular Diversity; Moos, W. H.; Pavia, M. R.; Ellington, A. D.; Kay, B. K., Eds.; ESCOM: Leiden, The Netherlands, 1997; Vol. 1, pp. 326-344; Hermkens, P. H. H.; Ottenheijm, H. C. J.; Rees, D. C., Tetrahedron 1997, 53, 5643-5678; Thompson, L. A.; Ellman, J. A., Chem. Rev. 1996, 96, 555-600.
4. 2. Reviews for solid-phase organic reactions, see: James, I. W.: A Compendium of Solid-Phase Chemistry Publications. In Annual Reports in Combìnatorial Chemistry and Molecular Diversity; Moos, W. H.; Pavia, M. R.; Ellington, A. D.; Kay, B. K., Eds.; ESCOM: Leiden, The Netherlands, 1997; Vol. 1, pp. 326-344; Hermkens, P. H. H.; Ottenheijm, H. C. J.; Rees, D. C., Tetrahedron 1997, 53, 5643-5678; Thompson, L. A.; Ellman, J. A., Chem. Rev. 1996, 96, 555-600.
5. 3. For hydrogenation and hydroformylation catalyzed by polymer-supported Rh(I)-phosphine complexes, see: Dumont, W.; Poulin, J.-C.; Dang, T.-P.; Kagan, H. B., J. Am. Chem. Soc. 1973, 95, 8295-8299; Takaishi, N.; Imai, H.; Bertelo, C. A.; Stille, J. K., J. Am. Chem. Soc. 1978, 100, 264-268; Bayer, E.; Schurig, V., Chemtech 1976, 212-214.
6. 3. For hydrogenation and hydroformylation catalyzed by polymer-supported Rh(I)-phosphine complexes, see: Dumont, W.; Poulin, J.-C.; Dang, T.-P.; Kagan, H. B., J. Am. Chem. Soc. 1973, 95, 8295-8299; Takaishi, N.; Imai, H.; Bertelo, C. A.; Stille, J. K., J. Am. Chem. Soc. 1978, 100, 264-268; Bayer, E.; Schurig, V., Chemtech 1976, 212-214.
7. 3. For hydrogenation and hydroformylation catalyzed by polymer-supported Rh(I)-phosphine complexes, see: Dumont, W.; Poulin, J.-C.; Dang, T.-P.; Kagan, H. B., J. Am. Chem. Soc. 1973, 95, 8295-8299; Takaishi, N.; Imai, H.; Bertelo, C. A.; Stille, J. K., J. Am. Chem. Soc. 1978, 100, 264-268; Bayer, E.; Schurig, V., Chemtech 1976, 212-214.
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9. 5. For an example of asymmetric hydrogenation using chiral phosphine ligands loaded on Multipin system, see: Gilbertson, S. R.; Wang, X., Tetrahedron Lett. 1996, 37, 6475-6478.
10. 6. Takahashi, T.; Machida, K.; Kido, Y.; Nagashima, K.; Ebata, S.; Doi, T., Chem. Lett. 1997, 1291-1292.
11. 7. For Multipin approach, see: Valerio, R. M.; Bray, A. M.; Maeji, N. J., Int. J. Peptide Protein Res. 1994, 44, 158-165; Virgilio, A. A.; Ellman, J. A., J. Am. Chem. Soc. 1994, 116, 11580-11581; Valerio, R. M.; Bray, A. M.; Patsiouras, H., Tetrahedron Lett. 1996, 37, 3019-3022; Rodebaugh, R.; Joshi, S.; Fraser-Reid, B.; Geysen, H. M., J. Org. Chem. 1997, 62, 5660-5661.
12. 7. For Multipin approach, see: Valerio, R. M.; Bray, A. M.; Maeji, N. J., Int. J. Peptide Protein Res. 1994, 44, 158-165; Virgilio, A. A.; Ellman, J. A., J. Am. Chem. Soc. 1994, 116, 11580-11581; Valerio, R. M.; Bray, A. M.; Patsiouras, H., Tetrahedron Lett. 1996, 37, 3019-3022; Rodebaugh, R.; Joshi, S.; Fraser-Reid, B.; Geysen, H. M., J. Org. Chem. 1997, 62, 5660-5661.
13. 7. For Multipin approach, see: Valerio, R. M.; Bray, A. M.; Maeji, N. J., Int. J. Peptide Protein Res. 1994, 44, 158-165; Virgilio, A. A.; Ellman, J. A., J. Am. Chem. Soc. 1994, 116, 11580-11581; Valerio, R. M.; Bray, A. M.; Patsiouras, H., Tetrahedron Lett. 1996, 37, 3019-3022; Rodebaugh, R.; Joshi, S.; Fraser-Reid, B.; Geysen, H. M., J. Org. Chem. 1997, 62, 5660-5661.
14. 7. For Multipin approach, see: Valerio, R. M.; Bray, A. M.; Maeji, N. J., Int. J. Peptide Protein Res. 1994, 44, 158-165; Virgilio, A. A.; Ellman, J. A., J. Am. Chem. Soc. 1994, 116, 11580-11581; Valerio, R. M.; Bray, A. M.; Patsiouras, H., Tetrahedron Lett. 1996, 37, 3019-3022; Rodebaugh, R.; Joshi, S.; Fraser-Reid, B.; Geysen, H. M., J. Org. Chem. 1997, 62, 5660-5661.
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20. 2-Polystyrene, Batch no. 810-1. Loading = 9.5 μmol per crown, Chiron Technologies Pty. Ltd., 11 Duerdin St., Clayton, Victoria 3168, Australia.
21. 1H NMR: 8 × 300 mm Senshu Pak, Silica3301-N, elution 20% ethyl acetate / hexane, flow rate 3.0 mL /min, 3: Rt = 9.5-11.6 min; 4: 20.8-25.0 min; 5: 12.5-13.9 min; 6: 16.5-19.3 min.
22. 14. The partial cleavage (30-45%) was observed by TLC analysis of the solution of the reaction mixture. The concentrated residue of the reaction solution and washed solvents was analyzed by HPLC in the same concentration as that of the crude products shown in Table 1. This partial cleavage was less than 5% when the reaction was carried out at 40 °C for 40 h.