Conjugate addition of organocopper reagents in dichloromethane to α,β-unsaturated esters

Tetrahedron Letters

Volumn 48, Issue 44, 2007, Pages 7887-7889

  Yang, Jingyue ^a   Dudley, Gregory B ^a  

^a FLORIDA STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

COPPER DERIVATIVE; CUPRATE; DICHLOROMETHANE; ESTER DERIVATIVE; LEWIS ACID; REAGENT; UNCLASSIFIED DRUG;

ADDITION REACTION; ARTICLE; CHEMICAL STRUCTURE; CONJUGATION; CROSS COUPLING REACTION; DIASTEREOISOMER; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; STRUCTURE ANALYSIS;

EID: 34848826226     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2007.08.105     Document Type: Article

References (24)

1. Salamone S.G., and Dudley G.B. Org. Lett. 7 (2005) 4443-4445
2. For a review of the chemistry and biology of roseophilin and related compounds, see:. Fürstner A. Angew. Chem., Int. Ed. 42 (2003) 3582-3603
3. Woodward S. Angew. Chem., Int. Ed. 44 (2005) 5560-5562
4. In: Krause N. (Ed). Modern Organocopper Chemistry (2002), Wiley-VCH, Weinheim
5. Nakamura E., and Mori S. Angew. Chem., Int. Ed. 39 (2000) 3750-3771
6. Krause N., and Gerold A. Angew. Chem., Int. Ed. 36 (1997) 186-204
7. Lipshutz B.H., and Sengupta S. Org. React. 41 (1992) 135-631
8. Yamamoto Y. Angew. Chem., Int. Ed. Engl. 25 (1986) 947-1038
9. Perlmutter P. Conjugate Addition Reactions in Organic Synthesis (1992), Pergammon, Oxford
10. Alkylcuprates, particularly secondary alkylcuprates, that possess β-hydrogens are susceptible to β-hydride elimination and other disproportionation pathways that are not available to aryl- or vinylcuprates.
11. Yang, J.; Katukojvala, S.; Dudley, G. B., unpublished results to be disclosed at a future date.
12. Bergdahl M., Lindstedt E.-L., Nilsson M., and Olsson T. Tetrahedron 44 (1988) 2055-2062
13. Related work:. Johnson C.R., and Marren T.J. Tetrahedron Lett. 28 (1987) 27-30
14. Bergdahl M., Lindstedt E.-L., Nilsson M., and Olsson T. Tetrahedron 45 (1989) 535-543
15. Bergdahl M., Eriksson M., Nilsson M., and Olsson T. J. Org. Chem. 58 (1993) 7238-7244
16. Eriksson M., Nilsson M., and Olsson T. Synlett (1994) 271-272
17. Bergdahl M., Iliefski T., Nilsson M., and Olsson T. Tetrahedron Lett. 36 (1995) 3227-3230
18. Eriksson M., Hjelmencrantz A., Nilsson M., and Olsson T. Tetrahedron 51 (1995) 12631-12644
19. Eriksson M., Johansson A., Nilsson M., and Olsson T. J. Am. Chem. Soc. 118 (1996) 10904-10905
20. 3SiI.
21. 2 at -78 °C. The reaction mixtures were allowed to warm, typically to room temperature, and monitored for consumption of the activated alkene. Standard aqueous workup and purification techniques were employed to isolate the pure conjugate addition products. See Supplementary data for complete details and characterization data.
22. Dambacher J., Anness R., Pollock P., and Bergdahl M. Tetrahedron 60 (2004) 2097-2110
23. Bertz S.H., Miao G., Rossiter B.E., and Snyder J.P. J. Am. Chem. Soc. 117 (1995) 11023-11024
24. House H.O., Respess W.L., and Whitesides G.M. J. Org. Chem. 31 (1966) 3128-3141