2-Diethoxyphosphoryl-4-nitroalkanoates -: Versatile intermediates in the synthesis of α-alkylidene-γ-lactones and lactams

被引：33

作者：

Blaszczyk, E ^{[1
]}

Krawczyk, H ^{[1
]}

Janecki, T ^{[1
]}

机构：

[1] Tech Univ Lodz, Inst Organ Chem, PL-90924 Lodz, Poland

来源：

SYNLETT | 2004年 / 15期

关键词：

Michael addition; nitroalkanoates; Wittig type olefination; alpha-alkylidenelactones; alpha-methylidenelactams;

D O I：

10.1055/s-2004-835656

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Michael addition of various nitroalkanes 7a-f to ethyl (2-dietboxyphosphoryl)acrylate (6) gave 2-diethoxyphosphoryl-4-nitroalkanoates 8a-f. Transformation of the nitro functionality into hydroxy or amino group and cyclization yielded 3-(diethoxyphosphoryl)tetrahydro-2-furanones 11a-e or 3-(diethoxyphosphoryl)pyrrolidin-2-ones 14a-e, respectively. These compounds were then used in Horner-Wadsworth-Emmons olefinations of aldehydes to give 3-alkylidenedihydrofuran-2-ones 12a-e or 17a-c and 3-methylidenepyrrolidin-2-ones 15a-e.

引用

页码：2685 / 2688

页数：4

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