Synthesis of 3-acetonyl- and 3-(2-oxoethyl)glutarates

被引：13

作者：

Amat, M ^{[1
]}

Bassas, O ^{[1
]}

Cantó, M ^{[1
]}

Llor, N ^{[1
]}

Santos, MMM ^{[1
]}

Bosch, J ^{[1
]}

机构：

[1] Univ Barcelona, Fac Pharm, Organ Chem Lab, E-08028 Barcelona, Spain

来源：

TETRAHEDRON | 2005年 / 61卷 / 32期

关键词：

delta-oxodiesters; 3-acetonylglutarates; 3-(2-oxoethyl)glutarates; bis-homologation; ozonolysis; conjugate addition;

D O I：

10.1016/j.tet.2005.05.084

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Several synthetic routes to 3-acetonyl- and 3-(2-oxoethyl)glutarates 1-5 have been explored. The most advantageous involves, as the key steps, the conjugate addition of an appropriately substituted vinyl magnesium bromide to an alkylidenemalonic ester, a bis-homologation of the resulting diester and, finally, the reductive ozonolysis of the carbon-carbon double bond. The synthesis can be satisfactorily conducted in good overall yield on a multigram scale. (c) 2005 Elsevier Ltd. All rights reserved.

引用

页码：7693 / 7702

页数：10

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