Highly enantioselective catalytic asymmetric automultiplication of chiral pyrimidyl alcohol

Journal of the American Chemical Society

Volumn 118, Issue 2, 1996, Pages 471-472

  Shibata, Takanori ^a   Morioka, Hiroshi ^a   Hayase, Tadakatsu ^a   Choji, Kaori ^a   Soai, Kenso ^a  

^a TOKYO UNIVERSITY OF SCIENCE   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000235486     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja953066g     Document Type: Article

References (32)

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20. 1H NMR analysis of the corresponding (S)-α-methoxy-α-(trifluoromethyl)phenylacetic acid (MTPA) esters (Otani, I.; Kusumi, T.; Kashman, Y.; Kakisawa, H. J. Am. Chem. Soc. 1991, 113, 4092).
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24. A preliminary examination of the relation between the reaction time and the yield of the newly formed 2a using (S)-2a with 92.6% ee as a chiral catalyst revealed that the reaction rate is accelerated during the initial 2.5 h. Time, yield: 1.0 h. 3.9%; 2.0 h, 19.6%; 2.5 h. 42.0%.
25. The ee's of 2a,b were increased to 99.0% (2a) and 99.9% (2b) ee by the recrystallization of their (-)-camphanic esters. Cf.: (a) Bolm, C.; Ewald, M.; Felder, M.; Schlingloff, G. Chem. Ber. 1992, 125, 1169. (b) Lampe, D.; Mills, S. J.; Porter, B. V. L. J. Chem. Soc., Perkin Trans. 1 1992, 2899.
26. The ee's of 2a,b were increased to 99.0% (2a) and 99.9% (2b) ee by the recrystallization of their (-)-camphanic esters. Cf.: (a) Bolm, C.; Ewald, M.; Felder, M.; Schlingloff, G. Chem. Ber. 1992, 125, 1169. (b) Lampe, D.; Mills, S. J.; Porter, B. V. L. J. Chem. Soc., Perkin Trans. 1 1992, 2899.
27. Gupton, J. T.; Gall, J. E.; Riesinger, S. W.; Smith, S. Q.; Bevirt, K. M.; Sikorski, J. A.; Dahl, M. L.; Arnord, Z. J. Heterocycl. Chem. 1991, 28, 1281.
28. The use of (S)-2b with 89.8% ee as a chiral catalyst afforded (S)-2b (including catalyst) with 93.1% ee. (Observation by T. Shibata).
29. Automultiplication of (S)-1-(2-ethyl-5-pyrimidyl)-1-propanol (88.5% ee) in the presence of diethylzinc and 2-ethylpyrimidine-5-carbaldehyde was also observed, but with low ee (13.1% ee).
30. 3: Okamoto, M.; Fujii, T.; Tanaka, T. Tetrahedron 1995, 51, 5543. Okamoto, M.; Tabe, M.; Fujii, T.; Tanaka, T. Tetrahedron: Asymmetry 1995, 6, 767.
31. 3: Okamoto, M.; Fujii, T.; Tanaka, T. Tetrahedron 1995, 51, 5543. Okamoto, M.; Tabe, M.; Fujii, T.; Tanaka, T. Tetrahedron: Asymmetry 1995, 6, 767.
32. 3: Okamoto, M.; Fujii, T.; Tanaka, T. Tetrahedron 1995, 51, 5543. Okamoto, M.; Tabe, M.; Fujii, T.; Tanaka, T. Tetrahedron: Asymmetry 1995, 6, 767.