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
收藏
页码：5457 / 5460
页数：4
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