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Chiral Homoenolate Equivalents, III Asymmetric Synthesis of 3-Substituted 3-Phenylketones via Metallated SMP-Allylamines
Ahlbrecht, Hubertus,Sommer, Horst
, p. 829 - 836 (2007/10/02)
The diastereomeric excess obtained in alkylation reactions of the chiral homoenolate equivalents 7 with prolinol ether as chiral auxiliary leading to the formation of 3-phenylketones 9 clearly depends on the temperature, the counter ion and the size of the alkyl iodide.But most important is the influence of the solvent used.By its variation even the course of induction may be controlled.Normally, the selectivity amounts to about 8:1 only.The best results (about 9:1) are obtained with lithium as counter ion and tert-butyl methyl ether as solvent.
