Science of Synthesis

Frost, C. G.; Le Nôtre, J., Science of Synthesis, (2008) 36, 327.

The first example of a Barbier-type addition of allyl halides to carbonyl compounds mediated by indium was reported in 1988.[‌360‌] Since then a wide variety of allylic substrates gave been utilized in the addition of allylic indium reagents to aldehydes and ketones.[‌361‌–‌365‌] An unusual feature of the addition of allylic indium reagents is that the reactions are preferably performed in water or water-containing solvents. This is illustrated in the stereoselective indium-promoted allylations of β-hydroxy aldehydes in water.[‌366‌] The free hydroxy derivatives react with excellent diastereofacial control to afford anti-1,3-diols such as ‌121A‌ (‌Scheme 68‌).

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References

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• 8.Meeeee-Meee, (8888) M 88e, 8888.