75834-25-2Relevant academic research and scientific papers
Chiral Homoenolate Equivalents, II. - Asymmetric Synthesis of 3-Substituted 3-Phenylpropionaldehydes via Metallated Chiral Cinnamylamines
Ahlbrecht, Hubertus,Enders, Dieter,Santowski, Ludger,Zimmermann, Gerd
, p. 1995 - 2004 (2007/10/02)
The diastereomeric excess obtained in alkylation reactions of the chiral homoenolate equivalent 22 with prolinol ether as chiral auxiliary leading to the formation of phenylpropionaldehydes 24 depends strongly on the solvent used.The structure of the alkylating reagent on the other hand is not important.The best results (about 9:1) are obtained in tert-butyl methyl ether as solvent.Other chiral auxiliaries testet were uneffective. - Key Words: Chiral homoenolate equivalents / Alkylation / Chiral 1-aminoallyl anions / Chiral aldehydes
CHIRAL HOMOENOLATE EQUIVALENTS. I. ASYMMETRIC SYNTHESIS OF β-SUBSTITUTED ALDEHIDES VIA METALATED CHIRAL ALLYLAMINES
Ahlbrecht, Hubertus,Bonnet, Gerhard,Enders, Dieter,Zimmermann, Gerd
, p. 3175 - 3178 (2007/10/02)
Metalated chiral allylamines of type 2 (M = Li, K) are used as chiral homoenolate equivalents and allow after alkylation and acidic hydrolysis asymmetric C-C bond formations to β-substituted aldehydes in enantiomeric excesses up to 67percent.
