The first case of diastereoselective cycloadditions of enantiopure nitrilimines in aqueous media

Tetrahedron Asymmetry

Volumn 15, Issue 7, 2004, Pages 1077-1079

  Molteni, Giorgio ^a  

^a UNIVERSITY OF MILAN   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

ACRYLIC ACID ETHYL ESTER; BICARBONATE; NITRILE; PYRAZOLE; TOLUENE;

AQUEOUS SOLUTION; ARTICLE; CHEMICAL REACTION KINETICS; CYCLOADDITION; DIASTEREOISOMER; ENANTIOMER; PRIORITY JOURNAL; ROOM TEMPERATURE; SYNTHESIS;

EID: 1642619101     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetasy.2004.02.006     Document Type: Article

References (20)

1. Caramella P., Grünanger P. Padwa A. 1,3-Dipolar Cycloaddition Chemistry. vol. 1:1984;Wiley-Interscience, New York. Chapter 3.
2. Guerra F.M., Mish M.R., Carreira E.M. Org. Lett. 2000;4265.
3. Garanti L., Molteni G., Pilati T. Tetrahedron: Asymmetry. 13:2002;1285.
4. Barluenga J., Fernàndez-Marì F., Aguilar E., Viado A.L., Olano B. Tetrahedron Lett. 39:1998;4887.
5. Barluenga J., Fernàndez-Marì F., Gonzàles R., Aguilar E., Revelli G.A., Viado A.L., Fañanas F.J., Olano B. Eur. J. Org. Chem. 2000;1773.
6. Agocs A., Benyei A., Somogyi L., Herczegh P. Tetrahedron: Asymmetry. 9:1998;3359.
7. Grubert L., Galley G., Pätzel M. Tetrahedron: Asymmetry. 7:1996;1137.
8. Tronchet J.J.M., Tronchet J.F., Barbalat-Rey F. Heterocycles. 36:1993;833.
9. Hydrazonoyl chlorides, 3a and 3b, were synthesised according to Ref. [4a].
10. 3) δ 1.61 (3H, d, J 6.5), 2.38 (3H, s), 5.18 (1H, q, J 6.5), 6.90 (1H, br s, J 7.2), 7.0-7.4 (9H, m), 8.18 (1H, br s).
11. For a typical run: a solution of 3 (2.0 mmol) and ethyl acrylate (0.60 g, 6.0 mmol) in dry toluene (10 mL) was treated with triethylamine (1.01 g, 10.0 mmol) and refluxed for the time indicated in the Table 1. The undissolved material was filtered off and the solvent evaporated under reduced pressure. The residue was taken up with chloroform (20 mL) and the solution slowly concentrated affording as the major product 5 as an amorphous powder, while the remaining solution contained diastereoisomeric 6.
12. For a typical run: a mixture of 3 (5.0 mmol), ethyl acrylate (1.50 g, 15.0 mmol), THAC (0.19 g, 0.5 mmol) and aqueous 5% sodium hydrogencarbonate (20 mL), was stirred at room temperature for the time indicated in Table 1. Filtration gave a residue, which was taken up with chloroform (20 mL) and the solution slowly concentrated affording pure 5 as an amorphous powder, while the remaining solution contained diastereoisomeric 6.
13. Houk K.N., Sims J., Duke R.E., Strozier R.W., George J.K. J. Am. Chem. Soc. 95:1973;7287.
14. Houk K.N., Sims J., Watts C.R., Luskus L.J. J. Am. Chem. Soc. 95:1973;7301.
15. Caramella P., Houk K.N. J. Am. Chem. Soc. 98:1976;6397.
16. 3) δ 1.32 (3H, t, J 6.9), 1.62 (3H, d, J 7.4), 2.28 (3H, s), 3.40 (1H, dd, J 18.1, 8.4), 3.51 (1H, dd, J 18.1, 12.1), 4.23 (2H, q, J 6.9), 4.84 (1H, dd, J 12.1, 8.4), 5.22 (1H, q, J 7.4), 6.88 (1H, br d, J 7.0), 7.0-7. 4 (9H, m).
17. Shimizu T., Hayashi Y., Nishio T., Teramura K. Bull. Chem. Soc. Jpn. 57:1984;787.
18. Huisgen R., Seidel M., Wallbillich G., Knupfer H. Tetrahedron. 17:1962;3.
19. Molteni G., Ponti A., Orlandi M. New J.Chem. 26:2002;1340.
20. Molteni G., Ponti A. New J. Chem. 26:2002;1346.