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- W2950984817 abstract "The enantiomeric enolates (R)- and (S)-2, generated by double deprotonation of (R)- and (S)-2-hydroxy-1,2,2-triphenylethyl acetate (1) („HYTRA”), are added to chiral aldehydes 4. It turnes out, that in this aldol reaction, the stereochemistry is largely determined by the configuration of the enolate 2 („reagent control”). Depending on the enantiomer of the reagent 1, which is combined with one of the enantiomerically pure aldehydes 4, either anti or syn adducts 11 and 12 are formed predominantly. The basic hydrolysis of the crude adducts 11/12 affords anti and syn carboxylic acids 5 and 6 in the corresponding diastereomeric ratios. By recrystallization of some of the mixtures 11/12, the esters 11c, 11e, and 11g are available in high diastereomeric and enantiomeric purity. Scope and limitations of the method are discussed.Reagenskontrolle bei der Addition von (R)- und (S)-(2-Hydroxy-1,2,2-triphenylethyl)acetat an chirale AldehydeDie durch Zweifachdeprotonierung von (R)- und (S)-(2-Hydroxy-1,2,2-triphenylethyl)acetat (1) („HYTRA”) erhaltlichen enantiomeren Enolate (R)- und (S)-2 werden an chirale Aldehyde 4 addiert. Es zeigt sich, das in dieser Aldolreaktion die Stereochemie weitgehend durch die Konfiguration des Enolats 2 bestimmt wird. Je nachdem, welches Enantiomer des Reagens 1 mit einem der enantiomerenreinen Aldehyde 4 kombiniert wird, bilden sich bevorzugt anti- oder syn-Addukte 11 und 12. Alkalische Hydrolyse der Rohaddukte 11/12 liefert anti- und syn-Carbonsuuren 5 und 6 in entsprechenden Diastereomerenverhaltnissen. Durch Umkristallisation einiger der Gemische 11/12 lassen sich die Ester 11c, 11e und 11g in hoher Diastereomeren- und Enantiomerenreinheit erhalten. Moglichkeiten und Grenzen der Methode werden diskutiert." @default.
- W2950984817 created "2019-06-27" @default.
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- W2950984817 date "1989-02-07" @default.
- W2950984817 modified "2023-09-27" @default.
- W2950984817 title "ChemInform Abstract: Reagent-Controlled Addition of (R)- and (S)-2-Hydroxy-1,2,2-triphenylethyl Acetate to Chiral Aldehydes." @default.
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- W2950984817 doi "https://doi.org/10.1002/chin.198906086" @default.
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