Reaction of peroxyacetals with silyl ketene acetals: synthesis of 3-peroxyalkanoates and 3-peroxyalkanals

被引：9

作者：

Dussault, PH ^{[1
]}

Lee, RJ ^{[1
]}

Schultz, JA ^{[1
]}

Suh, YS ^{[1
]}

机构：

[1] Univ Nebraska, Dept Chem, Lincoln, NE 68588 USA

来源：

TETRAHEDRON LETTERS | 2000年 / 41卷 / 29期

关键词：

D O I：

10.1016/S0040-4039(00)00914-X

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Lewis acid-mediated reaction of monoperoxyacetals with silyl ketene acetals (SKAs) provides an efficient approach to 3-peroxyalkanoates. Propionate SKAs react with aliphatic peroxyacetals to furnish 3-peroxy-2-methyl alkanoates with modest anti-selectivity. Although acetate and thioacetate SKAs are less reactive, the latter react with unsaturated peroxyacetals to furnish peroxyalkenoates and -alkadienoates which undergo chemoselective reduction to 3-peroxyalkenals and 3-peroxyalkadienals. (C) 2000 Elsevier Science Ltd. All rights reserved.

引用

页码：5457 / 5460

页数：4

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