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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 information


J. Chem. Soc., Perkin Trans. 1, 1998, 2231-2234
Article type
Paper

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, 2231
DOI: 10.1039/A804230F

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