Organometallic Compounds of Zinc as Selective Nucleophilic Reagents in Organic Synthesis

References

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• Methyl (ethyl) substitution at the position only slightly affects self coupling in the presence of zinc metal2b: under these conditions γ-bromomethyl pent-2-enoate affords in 47.5% yields the expected methyl 5-carbo methoxy-4,7-dimethyl-hepta-2,6-dienoate as about 1.5/1 diastereoisomeric mixture IR (liquid film) 1735, 1730 cm-1; 1H-NMR (CDC13)δ 7.05 [7.04, minor diastereoisomer] (1H, dd, J=16 Hz), 5.95 (1H, d, J=16 Hz), 5.75-5.45 (2H), 3.72 [3.62, minor diastereoisomer] (6H, s), 3.0-2.3 (2H), 1.7 (3H, dd, J=7 Hz), 1.05 (3H, d, J=7 Hz)
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