One-pot asymmetric autocatalytic reaction with remarkable amplification of enantiomeric excess

Tetrahedron Asymmetry

Volumn 8, Issue 11, 1997, Pages 1717-1719

  Shibata, Takanori ^a   Hayase, Tadakatsu ^a   Yamamoto, Jun ^a   Soai, Kenso ^a  

^a TOKYO UNIVERSITY OF SCIENCE   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOL DERIVATIVE; ALKANOL;

ARTICLE; CATALYSIS; CHEMICAL REACTION; CHIRALITY; ENANTIOMER; PRIORITY JOURNAL; STEREOISOMERISM;

EID: 0030969970     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(97)00183-3     Document Type: Article

References (15)

1. For the implication of asymmetric autocatalysis, see: Wynberg, H. J. Macromol.-Sci. Chem., 1989, A26, 1033-1041.
2. Soai, K.; Niwa, S.; Hori, H. J. Chem. Soc., Chem. Commun., 1990, 982-983.
3. For asymmetric autoinduction, where a chiral source and a product after acid treatment have the same structure and configuration, see Alberts, A. H.; Wynberg, H. J. Am. Chem. Soc., 1989, 111, 7265-7266; ShengJian, L.; Yaozhong, J.; Aiqiao, M.; Guishu, Y. J. Chem. Soc., Perkin Trans. 1, 1993, 885-886; Soai, K.; Inoue, Y.; Takahashi, T.; Shibata, T. Tetrahedron, 1996, 52, 13355-13362.
4. For asymmetric autoinduction, where a chiral source and a product after acid treatment have the same structure and configuration, see Alberts, A. H.; Wynberg, H. J. Am. Chem. Soc., 1989, 111, 7265-7266; ShengJian, L.; Yaozhong, J.; Aiqiao, M.; Guishu, Y. J. Chem. Soc., Perkin Trans. 1, 1993, 885-886; Soai, K.; Inoue, Y.; Takahashi, T.; Shibata, T. Tetrahedron, 1996, 52, 13355-13362.
5. For asymmetric autoinduction, where a chiral source and a product after acid treatment have the same structure and configuration, see Alberts, A. H.; Wynberg, H. J. Am. Chem. Soc., 1989, 111, 7265-7266; ShengJian, L.; Yaozhong, J.; Aiqiao, M.; Guishu, Y. J. Chem. Soc., Perkin Trans. 1, 1993, 885-886; Soai, K.; Inoue, Y.; Takahashi, T.; Shibata, T. Tetrahedron, 1996, 52, 13355-13362.
6. (a) Shibata, T.; Morioka, H.; Hayase, T.; Choji, K.; Soai, K. J. Am. Chem. Soc., 1996, 118, 471-472;
7. (b) Shibata, T.; Choji, K.; Morioka, H.; Hayase, T.; Soai, K. Chem. Commun., 1996, 751-752.
8. (a) Soai, K.; Shibata, T.; Morioka, H.; Choji, K. Nature, 1995, 378, 767-768;
9. (b) Shibata, T.; Choji, K.; Hayase, T.; Aizu, Y.; Soai, K. Chem. Commun., 1996, 1235-1236.
10. For non-autocatalytic asymmetric amplification, see (a) Puchot, C.; Samuel, O.; Dunach, E.; Zhao, S.; Agami, C.; Kagan, H. B. J. Am. Chem. Soc., 1986, 108, 2353-2357;
11. (b) Oguni, N; Matsuda, Y.; Kaneko, T. J. Am. Chem. Soc., 1988, 110, 7877-7878;
12. (c) Kitamura, M.; Okada, S.; Suga, S.; Noyori, R. J. Am. Chem. Soc., 1989, 111, 4028-4036.
13. 4a to give pure 2 (252.9 mg). HPLC analysis of obtained 2 using a chiral column (Daicel Chiralcel OC) showed it had an enantiomeric purity of 92.1% e.e.
14. Bada, J. L. Nature, 1995, 374, 594-595; Mason, S. Nature, 1985, 314, 400-401.
15. Bada, J. L. Nature, 1995, 374, 594-595; Mason, S. Nature, 1985, 314, 400-401.