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Chirale Homoenolat‐Äquivalente, III Asymmetrische synthese 3‐substituierter 3‐Phenylketone über metallierte SMP‐ Allylamine
Author(s) -
Abbrecht Hobertas,
Sommer Horst
Publication year - 1990
Publication title -
chemische berichte
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.667
H-Index - 136
eISSN - 1099-0682
pISSN - 0009-2940
DOI - 10.1002/cber.19901230430
Subject(s) - chemistry , diastereomer , allylamine , solvent , ether , alkylation , medicinal chemistry , selectivity , alkyl , diethyl ether , iodide , lithium (medication) , stereochemistry , organic chemistry , catalysis , endocrinology , polymer , medicine , polyelectrolyte
Chiral Homoenolate Equivalents, 111. – Asymmetric Synthesis of 3‐Substituted 3‐Phenylketones via Metallated SMP‐ Allylamines 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.