Regioselectivity and diastereoselectivity in the phase transfer catalysed Michael addition of 2-phenylcyclohexanone

Tetrahedron Letters

Volumn 38, Issue 13, 1997, Pages 2359-2362

  Díez Barra, Enrique ^a   De La Hoz, Antonio ^a   Merino, Sonia ^a   Sánchez Verdú, Prado ^a  

^a UNIVERSITY OF CASTILLA LA MANCHA   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

CYCLOHEXANONE DERIVATIVE; KETONE;

ARTICLE; CATALYSIS; CHIRALITY; DRUG SYNTHESIS; IN VITRO STUDY; METHODOLOGY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0031592607     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)00348-1     Document Type: Article

References (8)

1. 1. Bram, G.; Loupy, A.; Sansoulet, J. Isr. J. Chem, 1985, 26, 291.
2. 2. a) Dolling, U. H.; Davis, P.; Grabowski, J. J. J. Am. Chem. Soc., 1984, 106, 446.
3. b) O'Donnell, M. J.; Bennett, W. D.; Wu, S. J. Am. Chem. Soc., 1989, 111, 2353.
4. c) Loupy, A.; Zaparucha, A. Tetrahedron Lett. 1993, 34, 473.
5. 3, δ): 25.831, 25.97, 34.51, 37.44, 40.81, 41.71, 43.90, 55.39, 58.60, 126.23, 126.94, 128.18, 128.21, 128.47, 128.79, 138.32, 142.90, 210.75, 213.52.
6. 4. Ouvrad N.; Rodríguez J.; Santelli M. Angew. Chem., Int. Ed. Engl., 1992, 31, 1651.
7. 5 General procedure. A mixture of 2-phenylcyclohexanone (1.5 mmol), base (6% mol) and catalyst (6% mol) was stirred for 5 minutes. The Michael acceptor (1.5 mmol) was then added and the reaction mixture was kept at 60°C for 24 hours. The crude mixture was extracted with dichloromethane (20 mL) and filtered. Removal of solvent and column chromatography yielded the pure products.
8. 6. Reaction conditions for the preparation of 2: A mixture of 2-phenylcyclohexanone (1.5 mmol), potassium tertbutoxide (6% mol) and TBAB (6% mol) was stirred for 5 minutes. Chalcone (1.5 mmol) was then added and the reaction mixture was kept at 60°C for 24 hours.