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- W2953008377 abstract "A chiral pyrrolidinylmethanol derivative containing perfluoro-ponytails (5) was prepared from (S)-proline. The use of this perfluoro-substituted amino alcohol in catalytic asymmetric additions of organozinc reagents to aldehydes affords products with high enantioselectivities in both pure hexane and a mixture of hexane and FC-72 (perfluorohexane). Enantiomeric excesses up to 94 and 88 % ee have been achieved in Et(2)Zn and Ph(2)Zn additions, respectively. For the reactions in the biphasic solvent system a striking temperature effect was observed. Thus, when the temperature was raised from 0 to 40 degrees C the ee value of the product increased from 81 to 92 %. Furthermore, the catalyst loading could be remarkably low, and with only 0.1 mol % of amino alcohol 5 a product with 90 % ee was obtained in the Et(2)Zn addition to benzaldehyde in hexane. The perfluoro-ligand was easily recovered by simple phase separation, and until the ninth repetition its reuse proceeded without significant loss of enantioselectivity and reactivity." @default.
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- W2953008377 date "2006-04-04" @default.
- W2953008377 modified "2023-09-27" @default.
- W2953008377 title "Asymmetric Diethyl- and Diphenylzinc Additions to Aldehydes by Using a Fluorine-Containing Chiral Amino Alcohol: A Striking Temperature Effect on the Enantioselectivity, a Minimal Amino Alcohol Loading, and an Efficient Recycling of the Amino Alcohol." @default.
- W2953008377 cites W2078872606 @default.
- W2953008377 doi "https://doi.org/10.1002/chin.200614032" @default.
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