Nucleophilic Addition of Potassium O-Ethyl Dithiocarbonate to Baylis-Hillman Adducts Using 9-BBN as Catalyst
DOI:
https://doi.org/10.29356/jmcs.v53i2.1006Keywords:
Xanthates, Baylis-Hillman adducts, 9-BBN as a Lewis acidAbstract
An efficient diastereoselective Michael addition of the commercial potassium O-ethyl dithiocarbonate to Baylis-Hillman adducts in the presence of 9-BBN (9-borabicyclo[3.3.1]nonane) as a Lewis acid is reported. 9-BBN both protected the hydroxyl group and activated the carbonyl of the Michael acceptor.
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References
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7. Crystal structure has been deposited at the Cambridge Crystallographic Data Centre: CCDC (739264). Unit cell parameters: a 6.6820(7) b 7.3796(8) c 23.075(3), alpha 87.113(2) beta 81.463(2) gamma 83.056(2), space group P-1.
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2. a) Pringle, W.; Sharpless, B.. Tetrahedron Lett. 1999, 40, 51515154. b) Shi, M.; Jiang, J.; Cui, S.; Feng, Y.. J. Chem. Soc., Perkin Trans 1. 2001, 390-393.
3. a) Basavaiah, D.; Dhrama Rao, P.; Suguna Hyma, R. Tetrahedron. 1996, 52, 8001-8062. b) Bulliard, M.; Zeitz, H.; Giese, B. Synlett 1991, 423-424. c) Kamimura, A.; Morita, R.; Matsuura, K.; Omata, Y.; Shirai, M. Tetrahedron Lett. 2002, 43, 6189-6191.
4. a) Zard, S.Z. Angew. Chem. Int. Ed. Engl. 1997, 36, 672-685. b) Quiclet-Sire, B.; Zard, S.Z. Chem. Eur. J. 2006, 12, 6002-6016.
5. Bernard, J.; Favier, A.; Zhang, L.; Nilasaroya, A.; Davis, T.P.; Barner-Kowollik, C.; Stenzel, M.H. Macromolecules. 2005, 38, 5475-5484.
6. a) Stentiford, R. Synlett. 2000, 1, 159. b) Bar-Haim, G.; Kol, M. Org. Lett 2004, 6, 3549-3551. c) Syed, B.M.; Gustafsson, T.; Kihlberg, J. Tetrahedron. 2004, 60, 5571-5575. d) Gawdzik, B.; Iwanek, W. Tetrahedron Assymm. 2005, 16, 2019-2023.
7. Crystal structure has been deposited at the Cambridge Crystallographic Data Centre: CCDC (739264). Unit cell parameters: a 6.6820(7) b 7.3796(8) c 23.075(3), alpha 87.113(2) beta 81.463(2) gamma 83.056(2), space group P-1.
8. Mi, X.; Luo, S.; Cheng, J.-P. J. Org. Chem. 2005, 70, 2338-2341.
9. Coelho, F.; Almeida, W. P.; Veronese, D.; Mateus, C. R.; Silva Lopes, E. C.; Rossi, R. C.; Silveira, G. P. C.; Pavam, C. H Tetrahedron 2002, 58, 7437-7447.
10. (a) Sa, M. M.; Ramos, M. D.; Fernandes, L. Tetrahedron 2006, 62, 11652-11656. (b) Ciganek, E. Organic Reactions (Hoboken, NJ, United States) 1997, pp. 51.
11. Patil, S. N.; Liu, F. J. Org. Chem. 2007, 72, 6305-6308.
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2019-06-24
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