Chiral Zinc Amides as the Catalysts for the Enantioselective Addition of Diethylzinc to Aldehydes

Journal of Organic Chemistry

Volumn 62, Issue 11, 1997, Pages 3770-3771

  Prasad, K R K ^a   Joshi, N N ^a  

^a NATIONAL CHEMICAL LABORATORY   (India)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0011781060     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo970047b     Document Type: Article

References (15)

1. Noyori, R.; Kitamura, M. Angew. Chem., Int. Ed. Engl. 1991, 30, 49.
2. Oguni, N.; Omi, T. Tetrahedron Lett. 1984, 25, 2823.
3. Soai, K.; Niwa, S. Chem. Rev. 1992, 92, 833.
4. (a) Kitamura, M.; Suga, S.; Kawai, K.; Noyori, R. J. Am. Chem. Soc. 1986, 108, 6071.
5. (b) Soai, K.; Yokoyama, S.; Hayasaka, T. J. Org. Chem. 1991, 56, 4264.
6. Prepared by stirring the amino alcohol with a toluene solution of diethylzinc at room temperature for 10-15 min.
7. A similar outcome for this reaction has been reported earlier, see: Delair, P.; Einhorn, C.; Einhorn, J.; Luche, J. L. Tetrahedron 1995, 51, 165.
8. The ligand is recovered quantitatively as its hydrochloride after the workup. Incidentally, the observation ruled out any possibility of the corresponding acyclic imine-alkoxide as the intermediate.
9. Kanemasa, S.; Onimura, K. Tetrahedron 1992, 48 8631.
10. Itsuno, S.; Nakano, M.; Miyazaki, K.; Masuda, H.; Ito, K. J. Chem. Soc. Perkin Trans. 1 1985, 2039.
11. Pickard, R. H.; Kenyon, J. J. Chem. Soc. 1914, 1115.
12. Kang, J.; Lee, J. W.; Kim, J. I. J. Chem. Soc., Chem. Commun. 1994, 2009.
13. Chelucci, G.; Conti, S.; Falorni, M.; Giacomelli, G. Tetrahedron 1991, 47, 8251.
14. Watanabe, M.; Araki, S.; Butsugan, Y.; Uemura, M. J. Org. Chem. 1991, 56, 2218.
15. Levene, P. A.; Marker, R. E. J. Biol. Chem. 1932, 97, 379.