Science of Synthesis

Montgomery, J., Science of Synthesis, (2001) 1, 16.

The intermolecular process between simple dienes and aldehydes is reported by Tamaru.[‌31‌] Triethylborane is employed as the reducing agent, and yields are good for a variety of substituted electron-rich and electron-poor dienes. Interestingly, reactions employing triethylborane and bis(acetylacetonato)nickel(II) (‌1‌) produce 4,5-unsaturated alcohols (‌Scheme 9‌), whereas reactions employing bis(η4-cycloocta-1,5-diene)nickel(0) (‌2‌), triphenylphosphine, and triethylsilane produce 3,4-unsaturated silyl ethers. The mechanistic basis for this reversal of regioselectivity has not been established.

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References