Yadav, Jhillu S. ; Subba Reddy, Basi V. ; Yadav, Nagendra Nath ; Pratap Singh, Ashutosh ; Choudhary, Madavi ; Kunwar, Ajit C. (2008) Indium-mediated alkynylation of Baylis-Hillman acetates: a novel route to 1,4-enynes Tetrahedron Letters, 49 (42). pp. 6090-6094. ISSN 0040-4039
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Official URL: http://www.sciencedirect.com/science/article/pii/S...
Related URL: http://dx.doi.org/10.1016/j.tetlet.2008.08.019
Abstract
Baylis-Hillman acetates undergo smooth alkynylation with aryl-susbstituted iodoalkynes in the presence of indium metal in refluxing dichloromethane to furnish 1,4-enynes in high yields with (E)-stereoselectivity. In the absence of Lewis acid, the reaction follows both SN2 and SN2' pathways affording 1:1 mixtures of 1,4-enynes. Upon addition of 10 mol % of InBr3, the reaction proceeds preferably in the SN2' manner. In the case of adducts derived from acrylonitrile, the corresponding products are obtained in fairly good yields and with (Z)-stereoselectivity.
| Item Type: | Article |
|---|---|
| Source: | Copyright of this article belongs to Elsevier Science. |
| Keywords: | Indium Reagents; SN2' Substitution; Allylic Acetates; 1; 4-enynes |
| ID Code: | 63189 |
| Deposited On: | 28 Sep 2011 03:39 |
| Last Modified: | 28 Sep 2011 03:39 |
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