Enantioselective Functionalization of Prochiral Diols via Chiral Spiroketals: Preparation of Optically Pure 2-Substituted 1,3-Propanediol Derivatives and Asymmetric Synthesis of Chroman Ring and Side Chain of ce-Tocopherol

Journal of the American Chemical Society

Volumn 109, Issue 2, 1987, Pages 527-532

  Harada, Toshiro ^a   Hayashiya, Toshio ^a   Wada, Isao ^a   Iwa ake, Naoko ^a   Oku, Akira ^a  

^a KYOTO INSTITUTE OF TECHNOLOGY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000917197     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja00236a034     Document Type: Article

References (20)

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11. Reductive cleavage of the chiral ketals derived from (2R.,4R.)-2,4-pentanediol with use of organoaluminum reagents has been reported to proceed with the opposite stereoselectivity to that observed by Johnson et al. Mori, A.; Fujiwara, J.; Maruoka, K.; Yamamoto, H. Tetrahedron Lett. 1983, 24, 4581.
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17. For the previous asymmetric syntheses of side chains, see: (a) Scott, J. W.; Bizzarro, F. T.; Parrish, D. R.; Saucy, G. Helv. Chim. Acta 1976, 59, 290. (b) Schmid, M.; Barner, R. J. Org. Chem. 1979, 62, 464. (c) Leuenberger, H. G. W.; Bouguth, W.; Barner, R.; Schmid, M.; Zell, R. J. Org. Chem. 1979, 62, 454. (d) Zell, R. J. Org. Chem. 1979, 62, 474. (e) Trost, B. M.; Klun, T. P. J. Am. Chem. Soc. 1981, 103, 1864. (f) Helmchan, G.; Schmierer, R. Tetrahedron Lett. 1983, 24, 1235. (g) Koreeda, M.; Brown, L. J. Org. Chem. 1983, 48, 2122. (h) Fujiwara, J.; Fukutani, Y.; Hasegawa, M.; Maruoka, K.; Yamomoto, H. J. Am. Chem. Soc. 1984, 106, 5004. (i) Berube, G.; Deslongchamps, P. Can. J. Chem., 1984. 62. 1558.
18. For the previous asymmetric syntheses of the chroman ring, see: (a) Reference 15. (b) Fuganti, C.; Grasselli, P. J. Chem. Soc., Chem. Commun. 1982, 205. (c) Akkerman, J. M.; De Koning, H.; Huisman, H. O. Heterocycles 1981, 15, 797. (d) Solladie, G.; Moine, G. J. Am. Chem. Soc. 1984, 106. 6097.
19. Substitution of a benzyloxy group for the trimethylsilyloxy group was achieved in a single flask operation by this procedure. For the use of tetramethylammonium fluoride as a Lewis base in the protection of phenols, see: Miller, J. M.; So, K. H.; Clark, J. H. Can. J. Chem., 1979, 57, 1887.
20. Simon, P.; Ziegler, C. J.; Gross, B. Synthesis 1979, 951.