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26.1.9.5 Method 5: Monoalkylation of Magnesium Enolates

DOI: 10.1055/sos-SD-026-00361

Plaquevent, J.-C.; Cahard, D.; Guillen, F.Science of Synthesis, (200526481.

Due to the high level of synthetic interest associated with metal enolates, numerous variations in the enolate metallic counterion have been described. Most of these approaches were designed to increase selectivity in aldol-type reactions and so are not discussed in this section. For example, titanium,[‌59‌,‌60‌] zirconium,[‌61‌,‌62‌] cerium,[‌63‌] and tin[‌64‌] enolates are obtained either by transmetalation from lithium enolates or by cleavage of the corresponding enoxysilane. They are then usually used in aldol-type reactions with excellent results. Boron enolates, derivatives that are generally considered to contain highly covalent metaloxygen bonds, are beyond the scope of this section.[‌65‌]

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