Mechanisms of nucleophilic substitutions of acetals

被引：8

作者：

Bull, SD ^{[1
]}

Correia, LMARB ^{[1
]}

Davies, SG ^{[1
]}

机构：

[1] Univ Oxford, Dyson Perrins Lab, Oxford OX1 3QY, England

来源：

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1998年 / 15期

关键词：

D O I：

10.1039/a804230f

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The nucleophilic substitution of (+)-(R)-benzaldehyde methyl isopropyl acetal (alpha R)-1 (93% eel and (+)-(R)-o-anisaldehyde methyl isopropyl acetal (alpha R)-2 (homochiral) with Me2CuLi-BF3 . OEt2 occurs completely chemoselectively to afford (+)-(alpha R)-alpha-methyl(benzyl) isopropyl ether (+)-(alpha R)-3 (40% eel and (+)-(alpha R)-alpha-methyl(o-methoxybenzyl) isopropyl ether (+)-(alpha R)-4 (34% eel 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%.

引用

页码：2231 / 2233

页数：3

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