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https://doi.org/10.1002/asia.201100863
| Title: | Catalytic diastereoselective tandem conjugate addition-elimination reaction of Morita-Baylis-Hillman C adducts by C-C bond cleavage | Authors: | Yang, W. Tan, D. Lee, R. Li, L. Pan, Y. Huang, K.-W. Tan, C.-H. Jiang, Z. |
Keywords: | C-C bond cleavage catalysis density functional calculations diastereoselectivity Morita-Baylis-Hillman adducts |
Issue Date: | Apr-2012 | Citation: | Yang, W., Tan, D., Lee, R., Li, L., Pan, Y., Huang, K.-W., Tan, C.-H., Jiang, Z. (2012-04). Catalytic diastereoselective tandem conjugate addition-elimination reaction of Morita-Baylis-Hillman C adducts by C-C bond cleavage. Chemistry - An Asian Journal 7 (4) : 771-777. ScholarBank@NUS Repository. https://doi.org/10.1002/asia.201100863 | Abstract: | Through the cleavage of the C-C bond, the first catalytic tandem conjugate addition-elimination reaction of Morita-Baylis-Hillman C adducts has been presented. Various S N2′-like C-, S-, and P-allylic compounds could be obtained with exclusive E configuration in good to excellent yields. The Michael product could also be easily prepared by tuning the β-C-substituent group of the α-methylene ester under the same reaction conditions. Calculated relative energies of various transition states by DFT methods strongly support the observed chemoselectivity and diastereoselectivity. © 2012 Wiley-VCH Verlag GmbH&Co. KGaA, Weinheim. | Source Title: | Chemistry - An Asian Journal | URI: | http://scholarbank.nus.edu.sg/handle/10635/93240 | ISSN: | 18614728 | DOI: | 10.1002/asia.201100863 |
| Appears in Collections: | Staff Publications |
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