Highly stereoselective hydroformylation of olefins possessing chiral sugar templates

Synlett

Volumn , Issue 4, 1998, Pages 381-382

  Takahashi, Takashi ^a   Ebata, Satoshi ^a   Yamada, Haruo ^a  

^a TOKYO INSTITUTE OF TECHNOLOGY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001449130     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1998-1680     Document Type: Article

References (37)

1. Examples of synthesis of β-substituted aldehydes, see: (a) Yamada, K.; Ojika, M.; Ishigaki, T.; Yoshida, Y.; Ekimoto, H.; Arakawa, M. J. Am. Chem. Soc. 1993, 115, 11020.
2. (b) Cha, J. K.; Christ, W. J.; Finan, J. M.; Fujioka, H.; Kishi, Y.; Klein, L. L.; Ko, S. S.; Leder, J.; McWhorter Jr., W. W.; Pfaff, K.-P.; Yonaga, M.; Ueraura, D.; Hirata, Y. J. Am. Chem. Soc. 1982, 104, 7369.
3. (c) Sasaki, M.; Matsumori, N.; Maruyama, T.; Nonomura, T.; Murata, M.; Tachibana, K.; Yasumoto, T. Angew. Chem., Int. Ed. Engl. 1996, 35, 1672.
4. (d) Bottini, A. T.; Gilchrist, D. G. Tetrahedron Lett. 1981, 22, 2719.
5. (e) Bezuidenhout, S. C.; Gelderblom, W. C. A.; Gorst-Allman, C. P.; Horak, R. M.; Marasas, W. F. O.; Spiteller, G.; Vleggaar, R. J. Chem. Soc., Chem. Commun. 1988, 743.
6. Kozlowski, J. A. In Comprehensive Organic Synthesis, Trost. B. M.; Fleming, I.; Semmelhack, M. F. Eds.; Pergamon Press, Oxford, 1991, Vol. 4, 183.
7. For reviews of hydroformylation, see: (a) Cornils, B. In New Syntheses with Carbon Monoxide; Fable, J. Ed.; Springer-Verlag: New York, 1980.
8. (b) Tolman, C. A.; Faller, J. In Homogeneous Catalysis with Metal Phosphine Complexes; Pignolet, L. H. Ed.; Plenum Press: New York, 1983; Chapt. 2.
9. (c) Dickson, R. S. In Homogeneous Catalysis with Compounds of Rhodium and Iridium; Ugo, R.; James B. R. Eds.; D. Reidel Publish Company: Dordrecht, 1985.
10. (d) Beller, M.; Cornils, B.; Frohning, C.D.; Kohlpaintner, C. W. J. Mol. Cat. A, 1995, 104, 17.
11. For reviews of stereoselectivity in the rhodium-catalyzed hydroformylation, see: (a) Lazzaroni, R.; Pucci, S.; Bertozzi, S.; Pini, D. J. Organomet. Chem. 1983, 247, C56.
12. (b) Lazzaroni, F.; Biscarini, P.; Bordoni, S.; Longoni, G.; Venturini E. J. Organomet. Chem. 1996, 508, 59.
13. For a review of asymmetric hydroformylation, see: Agbossou, F.; Carpentier, J.-F.; Mortreux, A. Chem. Rev. 1995, 95, 2485.
14. For examples of asymmetric hydroformylation, see: (a) Nozaki, K.; Sakai, N.; Nanno, T.; Higashijima, T.; Mano, S.; Horiuchi, T.; Takaya, H. J. Am. Chem. Soc. 1997, 119, 4413 and references cited herein.
15. (b) Sakai, N.; Mano, S.; Nozaki, K.; Takaya, H. J. Am. Chem. Soc. 1993, 115, 7033.
16. For an example of diastereoselective hydroformylation, see: Leighton, J. L.; O'Neil, D, N.; J. Am. Chem. Soc. 1997, 119, 11118.
17. For examples of 1,1-disubstituted alkenes, see: (a) Botteghi, C.; Consiglio, G.; Ceccarelli, G.; Stefani, A. J. Org. Chem. 1972, 37, 1835.
18. (b) Hoffmann, W.; Siegel, H. Tetrahedron Lett. 1975, 533.
19. (c) Kollár, L.; Consiglio, G.; Pino, P. Chimia 1986, 40, 428.
20. (d) Gladiali, S.; Pinna, L. Tetrahedron: Asymmetry, 1991, 2, 623.
21. For examples of application to fine chemical synthesis, see: (a) Wuts, P. G. M.; Obrzut, M. L.; Thompson, P. A. Tetrahedron Lett. 1984, 25, 4051.
22. (b) Nozaki, K.; Li. W.; Horiuchi, T.; Takaya, H.; Saito, T.; Yoshida, A.; Matsumura, K.; Kato, Y.; Imai, T.; Miura, T.; Kumobayashi, H. J. Org. Chem. 1996, 61, 7658.
23. Takahashi, T.; Machida, K.; Kido, Y.; Nagashima, K.; Ebata, S.; Doi, T. Chem. Lett. 1997, 1291.
24. Doi, T.; Komatsu, H.; Yamamoto, K. Tetrahedron Lett. 1996, 37, 6877.
25. (a) Burke, S. D.; Cobb, J. E. Tetrahedron Lett. 1986, 27, 4237.
26. (b) Burke, S. D.; Cobb, J. E.; Takeuchi, K. J. Org. Chem. 1990, 55, 2138.
27. (c) Jackson, W. R.; Perlmutter, P.; Suh, G.-H. J. Chem. Soc., Chem. Commun. 1987, 724.
28. (d) Jackson, W. R.; Perlmutter, P.; Tasdelen, E. E. Tetrahedron Lett. 1990, 31, 2461.
29. (e) Jackson, W. R.; Moffat, M. R.; Perlmutter, P.; Tasdelen, E. E. Aust. J. Chem. 1992, 45, 823.
30. (f) Breit, B. Angew. Chem., Int. Ed. Engl. 1996, 35, 2835.
31. (g) Breit, B. Chem. Commun. 1997, 591.
32. Hanessian, S. In The Total Synthesis of Natural Products, The Chiron Approach, Pergamon Press, Oxford, 1983.
33. (a) Friesen, R. W.; Danishefsky, S. J. J. Am. Chem. Soc. 1989, 111, 6656.
34. (b) Halcomb, R. L.; Danishefsky, S. J. J. Am. Chem. Soc. 1989, 111, 6661.
35. Lewis, M. D.; Cha, J. K.; Kishi, Y. J. Am. Chem. Soc. 1982, 104, 4976.
36. The ratio was determined by HPLC analysis after conversion of the aldehydes 12 to the corresponding diols.
37. -1.