Indium(I)-mediated, tandem carbonyl addition-oxy-cope rearrangement of γ-pentadienyl anions to cyclohexenones and conjugated aromatic ketones

Synthesis

Volumn , Issue 5, 2003, Pages 790-794

  Villalva Servín, Nidia P ^a   Melekov, A ^a   Fallis, Alex G ^a  

^a UNIVERSITY OF OTTAWA   (Canada)

Author keywords

Conjugate addition; Indium; oxy Cope; 3,3 sigmatropic rearrangement; pentadienyl

Indexed keywords

ADDITION REACTIONS; CATALYSTS; CHEMICAL BONDS; INDIUM; NEGATIVE IONS;

AROMATIC CONJUGATED KETONES;

KETONES;

5 BROMOPENTA 1,3 DIENE; ALKADIENE; ANION; CARBONYL DERIVATIVE; GAMMA PENTADIENE; INDIUM; KETONE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL BOND; CHEMICAL STRUCTURE; CONJUGATION; REACTION ANALYSIS;

EID: 0037250762     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2003-38063     Document Type: Article

References (15)

1. (a) Woo, S.; Squires, N.; Fallis, A. G. Org. Lett. 1999, 1, 573.
2. (b) Hirashita, T.; Inoue, S.; Yamamura, H.; Kawai, M.; Araki, S. J. Organomet. Chem. 1997, 549, 305.
3. Negishi, E.-I. Organometallics in Organic Synthesis, Vol. 1; Wiley: New York, 1980, 30-59.
4. Woo, S.; Legoupy, S.; Parra, S.; Fallis, A. G. Org. Lett. 1999, 1, 1013.
5. Kwon, O.; Park, S. B.; Schreiber, S. L. J. Am. Chem. Soc. 2002, 124, 13402.
6. Melekhov, A.; Fallis, A. G. Tetrahedron Lett. 1999, 40, 7867.
7. (a) Gerard, F.; Miginiac, P. Bull. Soc. Chim. Fr. 1974, 1924.
8. (b) Wilson, S. R.; Mao, D. T.; Jernberg, K. M.; Ezmirly, S. T. Tetrahedron Lett. 1977, 2559.
9. Evans, D. A.; Nelson, J. V. J. Am. Chem. Soc. 1980, 102, 774.
10. Hrovat, D. A.; Beno, B. R.; Lange, H.; Yoo, H.-Y.; Houk, K. N.; Borden, W. T. J. Am. Chem. Soc. 1999, 121, 10529.
11. Doering, W. E. von; Wang, Y. J. Am. Chem. Soc. 1999, 121, 10112.
12. 2O (15 mL) and filtered through a silica pad and purified by flash chromatography.
13. Chan, T. H.; Yang, Y. J. Am. Chem. Soc. 1999, 121, 3228.
14. Forgione, P.; Wilson, P. D.; Yap, G. P. A.; Fallis, A. G. Synthesis 2000, 921.
15. Haeffner, F.; Houk, K. N.; Reddy, R.; Paquette, L. A. J. Am. Chem. Soc. 1999, 121, 11880.