125261-74-7Relevant academic research and scientific papers
Preparation of Some Chiral Aminodiols from Tartaric Acid. Chiral Lithium Aluminium Hydride Derivatives for Asymmetric Ketone Reductions
Schmidt, Manfred,Amstutz, Rene,Crass, Gerhard,Seebach, Dieter
, p. 1691 - 1707 (2007/10/02)
The nitrogen- and oxygen-substituted chiral diols 1 are prepared from tartaric or malic acid.For the introduction of the amino groups, tartaric acid derived electrophiles of increasing reactivity are used: The diester (-> 3), the ditosylate 4 (-> 5), the diepoxide 6 ( -> 1a, e, g, h), and the acyl chloride 7a.The alkylating reagents 9a and 10c, obtained from malic acid, are employed for the synthesis of 1i. - The diols 1 react with lithium aluminium hydride to give complexes, for which a cyclic structure 2 is assumed, and which reduce ketones with prochiral carbonyl C-atoms to optically active alcohols (Table 1 and 2).From the effect of substitution and from the sense of chirality of the predominantly formed enantiomers, several models 11 - 16 are discussed as possible mechanisms of this asymmetric synthesis.
