Asymmetric reduction of ketones with sodium aluminum hydride modified by various chiral diols

被引：1
|
作者：
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
机构：
[1] Russian Academy of Sciences,N. D. Zelinsky Institute of Organic Chemistry
[2] Cambrex Corporation,undefined
来源：
Russian Chemical Bulletin | 2000年 / 49卷
关键词：
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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摘要：
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.
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页码：460 / 465
页数：5
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