Synthesis of 3-substituted furans by directed lithiation and palladium catalysed coupling
DS Ennis, TL Gilchrist
Index: Ennis, David S.; Gilchrist, Thomas L. Tetrahedron, 1990 , vol. 46, # 7 p. 2623 - 2632
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Citation Number: 46
Abstract
The 5-position of the furan ring of 4, 4-dimethyl-2-(2-furyl) oxazoline (1a) was protected by a trimethylsityl group. The product, compound (2a), was then lithiated at the 3-position with sec- butyllithium and converted to the bromozinc species (2d) with zinc bromide. Coupling reactions with a range cf aryl-, acyl-, and vinyl halides were performed with Pd (PPh3) 4 as catalyst. The reaction with (l-bromoethenyl)-trimethylsilane is abnormal in that it gives a ...
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