Vinylalumination of activated carbonyl compounds

Tetrahedron Letters

Volumn 40, Issue 4, 1999, Pages 627-630

  Ramachandran, P Veeraraghavan ^a   Reddy, M Venkat Ram ^a   Rudd, Michael T ^a  

^a PURDUE UNIVERSITY   (United States)

Author keywords

keto esters; Acetylenic ketones; Acyl cyanides; Vinylalumination

Indexed keywords

ALUMINUM DERIVATIVE; CARBONYL DERIVATIVE; CYANIDE; ESTER; KETONE;

ARTICLE; CHEMICAL REACTION; SYNTHESIS;

EID: 0033593294     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)02504-0     Document Type: Article

References (12)

1. (a) Post-doctoral research associate on a grant from the Purdue Borane Research Fund.
2. (b) Pfizer Summer Undergraduate Research Fellow.
3. For the most recent review on Morita-Baylis-Hillman reaction, see: Ciganek, E. in Organic Reactions 1997, 51, 201. Paquette, L. A. ed. John Wiley, New York, NY.
4. Crouch, R. D.; Nelson, T. D. J. Chem. Ed. 1995, 72 (1), A6.
5. Golubev, A. S.; Galakhov, M. V.; Kolomiets, A. F.; Fokin, A. V. Izv. Akad. Nauk Ser. Khim. 1992, 2763.
6. Basavaiah. D.; Bharathi, T. K.; Gowriswari, V. V. L. Tetrahedron Lett. 1987, 28, 4351.
7. In the asymmetric reductions with Alpine-Borane, activated carbonyl compounds, such as α-acetylenic ketones, α-keto esters, and acyl cyanides undergo reaction within hours as compared to several days required for ordinary ketones. Brown, H. C.; Ramachandran, P. V. in Advances in Asymmetric Synthesis, Vol. 1. Hassner, A. Ed. JAI Press, Greenwich, CT, 1995, pp 144-210.
8. While acyl cyanides underwent an extremely slow reaction providing some product (TLC), the acetylenic ketone underwent a different type of condensation. Ramachandran, P. V.; Rudd, M. T.; Reddy, M. V. R. Manuscript in preparation.
9. (a) Tsuda, T.; Yoshida, T.; Saegusa, T. J. Org. Chem. 1988, 53, 1037.
10. (b) Zu, L. H.; Kundig, E. P. Helv. Chim. Acta 1994, 77, 1480.
11. (c) Génisson, Y.; Massardier, C.; Gautier-Luneau, I.; Greene, A. E. J. Chem, Soc. Perkin Trans. I 1996, 2869.
12. Ramachandran, P. V.; Reddy, M. V. R.; Rudd, M. T.; de Alaniz, J. R. Tetrahedron Lett. 1998, 39, 8791.