Asymmetric reduction of ketones with sodium aluminum hydride modified by various chiral diols |
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| Authors: | M. G. Vinogradov L. S. Gorshkova V. A. Pavlov O. V. Mikhalev G. V. Chel'tsova I. V. Razmanov V. A. Ferapontov O. R. Malyshev G. L. Heise |
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| Affiliation: | (1) N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky prosp., 117913 Moscow, Russian Federation;(2) Cambrex Corporation, One Meadowlands Plaza, 07073 East Rutherford, NJ, USA |
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| Abstract: | New stereoselective reducing reagents were preparedin situ by modification of NaAlH4 with various chiral diols. The efficiency of 1,4- and 1,3-diols as chiral auxiliaries in the reactions of alkyl aryl ketones with modified NaAlH4 was considerably higher than that of 1,2-diols. The effect of the nature of the achiral ligand additionally introduced into the chiral hydride reagent on the enantioselectivity of ketone reduction was studied. It was proposed that the sodium cation does not necessarily participate at the stage governing the reaction stereochemistry. Translated fromIzvestiya Akademii Nauk. Seriya Khimicheskaya, No. 3, pp 459–464, March, 2000. |
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| Keywords: | sodium aluminum hydride chiral diols, 1,1′ -bis-2-naphthol, α ,α ,α ′ ,α ′ -tetraaryl-1,3-dioxolane-4,5-dimethanols asymmetric reduction enantiomers ketones |
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