Science of Synthesis

Gribble, G. W., Science of Synthesis, (2006) 8, 375.

If steric effects from the use of ostensibly bulky alkyllithium reagents do not intervene, directing lithiation groups at the furan C3 position invariably effect C2 lithiation. Thus, under the Comins amino alkoxide conditions, furan-3-carbaldehyde is lithiated at C2 to give ‌39‌ upon methylation in high yield with greater than 96% regioselectivity (‌Scheme 24‌).[‌203‌] However, with bulkier lithium amides, C5 lithiation of furan-3-carbaldehyde occurs, e.g. to give ‌40‌.[‌204‌] Lithiation at C4 does not occur.

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References

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• 8.Meeeee-Meee, (8888) M 88e, 888.
• 8.Meeeee-Meee, (8888) M 8e, 888.
• 8.Meeeee-Meee, (8888) M 8e, 888.