Me MURRY

This reaction is related to the Fukuyama Indole Synthesis, both give 2,3-disubstituted indole derivatives. In addition, this reaction is very closely related to Me Murry Coupling in mechanism. 

A soln. of n-butyllithium in hexane added at a soln. of isopropylcyclohexylamine in tetrahydrofuran, then monoethyl malonate in tetrahydrofuran added, allowed to warm to 0° to form the 0,C-dianion, after 15 min. stirring dry hexamethylphosphoramide added followed by addition of allyl bromide in dry tetrahydrofuran, allowed to warm to room temp., stirred 2 hrs. to effect alkylation, then heated overnight at 68° ethyl 4-pentenoate. Y 80%. F. e. s. J. E. Me Murry and J. H. Musser, J. Org. Chem. 40, 2556 (1975). 

The degree of polymerization was determined by H-NMR-spectroscopy and MALDI TOP mass spectrometry. Results of H-NMR-spectroscopic investigations prove the defect-free structure and dW-trans configuration. In contrary to the product obtained by Me Murry reaction [19] or by sulfonium precursor route [20] there is no sign for any cis bonding (Figure 3, at the top, marked regions). 

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