Ranu, Brindaban C. ; Chattopadhyay, Kalicharan ; Jana, Ranjan (2007) Chemo-, regio- and stereoselective addition of triorganoindium reagents to acetates of Baylis-Hillman adducts: a new strategy for the synthesis of (E)- and (Z)-trisubstituted alkenes Tetrahedron Letters, 48 (22). pp. 3847-3850. ISSN 0040-4039
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Official URL: http://linkinghub.elsevier.com/retrieve/pii/S00404...
Related URL: http://dx.doi.org/10.1016/j.tetlet.2007.03.154
Abstract
The addition of several trialkyl or triarylindium reagents to the acetates of Baylis-Hillman adducts proceeds readily under the catalysis of copper and palladium derivatives. The reactions of trialkylindiums are catalyzed efficiently by CuI whereas additions of triarylindiums produce better results with Pd(PPh3)4. The reactions with 3-acetoxy-2-methylenealkanoates provide (E)-alkenes, whereas similar reactions with 3-acetoxy-2-methylenealkanenitriles lead to (Z)-alkenes. All the reactions are highly regio- and stereoselective and high yielding.
Item Type: | Article |
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Source: | Copyright of this article belongs to Elsevier Science. |
Keywords: | Triorganoindium; Baylis-Hillman Adduct; Trisubstituted Alkene; Copper(I) Iodide; Tetrakistriphenylphosphine Palladium |
ID Code: | 41472 |
Deposited On: | 30 May 2011 05:31 |
Last Modified: | 30 May 2011 05:31 |
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