An improved vinylalumination procedure replacing HMPA with NMO for the hydroalumination of α-acetylenic esters and ketones

Abstract

Replacing carcinogenic HMPA with NMO, a higher yielding, enviornmentally benign procedure for the vinylalumination of carbonyl compounds with [α-(ethoxycarbonyl)- vinyl]diisobutylaluminium and its β-methyl or -phenyl analogs, as well as [α-(acetyl)vinyl]diisobutylaluminium has been developed.

References

1. (a) T. Tsuda, T. Yoshida and T. Saegusa, J. Org. Chem., 1988, 53, 1037; (b) Y. Génisson, C. Massardier, I. Gautier-Luneau and A. E. Greene, J. Chem. Soc., Perkin Trans. 1, 1996, 2869; (c) L. H. Zu and E. P. Kundig, Helv. Chim. Acta, 1994, 77, 1480; (d) G. Li, H. X. Wei and S. Willis, Tetrahedron Lett., 1998, 39, 4607; (e) P. V. Ramachandran, M. V. R. Reddy, M. T. Rudd and J. R. de Alaniz, Tetrahedron Lett., 1998, 39, 8791; (f) P. V. Ramachandran, M. V. R. Reddy and M. T. Rudd, Tetrahedron Lett., 1999, 40, 627.
2. For the most recent review of the Morita–Baylis–Hillman reaction, see: E. Ciganek, Org. React., 1997, 51, 201.
3. J. F. Schmutz, Chem. Eng. News, 1978, 56(3), 39; H. Spencer, Chem. Ind., 1979, 728.
4. (a) T. Mukhopadhyay and D. Seebach, Helv. Chim. Acta, 1982, 65, 385; (b) E. Juaristi, P. Murer and D. Seebach, Synthesis, 1993, 1243; (c) I. A. O'Neil, J. Y. Q. Lai and D. Wynn, Chem. Commun., 1999, 56.