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25.1.15.4 Method 4: Reactions of Homoenolates

DOI: 10.1055/sos-SD-025-00247

Göttlich, R.Science of Synthesis, (200725388.

A three-carbon elongation to form aldehydes can be achieved by the reaction of electrophiles with homoenolates, which are formally aldehydes that are deprotonated in the β-position. Because the aldehyde homoenolate does not exist as such, two different types of homoenolate equivalent have been developed. The first type consists of β-haloaldehydes that are protected before substituting an organometallic group for the carbonhalogen bond. The second are various types of allylic metallic species carrying heteroatom substituents. This chemistry is the subject of several excellent reviews.[‌123‌‌125‌]

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