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Issue 15, 1998
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Mechanisms of nucleophilic substitutions of acetals

Abstract

The nucleophilic substitution of (+)-(R)-benzaldehyde methyl isopropyl acetal (αR)-1 (93% ee) and (+)-(R)-o-anisaldehyde methyl isopropyl acetal (αR)-2 (homochiral) with Me2CuLi–BF3·OEt2 occurs completely chemoselectively to afford (+)-(αR)-α-methyl(benzyl) isopropyl ether (+)-(αR)-3 (40% ee) and (+)-(αR)-α-methyl(o-methoxybenzyl) isopropyl ether (+)-(αR)-4 (34% ee) respectively, demonstrating that the mechanism of the former reaction involves a free oxonium ion to the extent of 56% and the latter to the extent of 66%.

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Article type: Paper
DOI: 10.1039/A804230F
Citation: J. Chem. Soc., Perkin Trans. 1, 1998,0, 2231-2234
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    Mechanisms of nucleophilic substitutions of acetals

    S. D. Bull, L. M. A. R. B. Correia and S. G. Davies, J. Chem. Soc., Perkin Trans. 1, 1998, 0, 2231
    DOI: 10.1039/A804230F

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