Silyl nitronates: Ismproved nitro-aldol reactions and reductive routes to 2-aminoalcohols

Journal of the Chemical Society, Chemical Communications

Volumn , Issue 16, 1978, Pages 689-691

  Colvin, Ernest W ^a   Seebach, Dieter ^a  

^a ETH ZURICH   (Switzerland)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 37049099459     PISSN: 00224936     EISSN: None     Source Type: Journal    
DOI: 10.1039/C39780000689     Document Type: Article

References (18)

1. P. A. S. Smith and D. R. Baer, Org. Reactions, 1960, 11, 157.
2. D. A. Evans, G. L. Carroll, and L. K. Truesdale, J. Org. Chem., 1974, 39, 914.
3. O. von Schickh, H. G. Padeken, and A. Segnitz, ‘Methoden der Organischen Chemie,’ (Houben-Weyl), Band X/1, Teil 1, Georg Thieme Verlag, Stuttgart, 1971.
4. H. J. Dauben, Jr., H. J. Ringold, R. H. Wade, and A. G. Anderson, Jr., J. Amer. Chem. Soc., 1951, 73, 2359.
5. W. C. Gakenheimer and W. H. Hartung, J. Org. Chem., 1944, 9, 85.
6. F. F. Blicke, N. J. Doorenbos, and R. H. Cox, J. Amer. Chem. Soc., 1952, 74, 2924.
7. (a) Further aspects of the chemistry of silyl nitronates will be published separately.
8. K. Torssell and O. Zeuthen, Acta Chem. Scand., 1978, B32, 118.
9. M. V. Kashutina, S. L. Ioffe, and V. A. Tartakovskii, Doklady Acad. Nauk. S.S.S.R., 1974, 218, 109.
10. 5 mol % of Fluka product was heated for 4 h at 90 °C and 0-1 mmHg.
11. R. Noyori, K. Yokoyama, J. Sakata, I. Kuwajima, E. Nakamura, and M. Shimuzu, J. Amer. Chem. Soc., 1977, 99, 1265. No reaction occurred in the absence of the catalyst, nor did the catalyst itself induce any reaction between the aldehyde and a nitroalkane.
12. G. Hesse and V. Jäger, Annalen, 1970, 740, 79.
13. S. Colonna, H. Hiemstra, and H. Wynberg, J.C.S. Chem. Comm., 1978, 238.
14. D. Seebach, R. Henning, F. Lehr, and J. Gonnermann, Tetrahedron Letters, 1977, 1161.
15. R. Henning, F. Lehr, and D. Seebach, Helv. Chim. Acta, 1976, 59, 2213.
16. D. Seebach and F. Lehr, Angew. Chem. Internat. Edn., 1976, 15, 505.
17. A. E. Pierce, ‘Silylation of Organic Compounds,’ Pierce Chemical Company, Rockford, Illinois, 1968, and references therein.
18. A. Dornow and M. Gellrich, Annalen, 1955, 594, 177, and references therein.