Gnaneshwar, Rudhramyna ; Sivaram, Swaminathan (2006) Conjugate addition of a silyl ketene acetal to α,β‐unsaturated lactones Synthetic Communications, 36 (7). pp. 885-890. ISSN 0039-7911
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Official URL: http://www.tandfonline.com/doi/abs/10.1080/0039791...
Related URL: http://dx.doi.org/10.1080/00397910500466058
Abstract
Conjugate addition of a silyl ketene acetal [Me2C=C(OMe)OSiMe3] to α,β‐unsaturated lactones (namely, 5,6‐dihydro-2H-pyran‐2‐one, 2(5H)‐furanone as Michael acceptor) occurs efficiently at room temperature in the presence of a nucleophilic catalyst, tetra‐n‐butyl ammonium bibenzoate (TBABB), in THF as well as Lewis acid catalysts such as Yb(OTf)3 and I2 in CH2Cl2, giving the corresponding 1,4‐adducts in excellent yields.
| Item Type: | Article |
|---|---|
| Source: | Copyright of this article belongs to Taylor and Francis Group. |
| Keywords: | 1,4‐Addition; Conjugate Addition; Cyclic α,β‐Unsaturated Esters; Electrophile; Lewis Acid; Michael Acceptor; Michael Addition; Mukaiyama–Michael Addition; O‐Silylated Ketene Acetal; Nucleopilic Catalyst |
| ID Code: | 70178 |
| Deposited On: | 18 Nov 2011 12:59 |
| Last Modified: | 18 Nov 2011 13:00 |
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