A short and efficient synthesis of (R,R)-2-methylcyclopropanecarboxylic acid

被引：24

作者：

Delhaye, Laurent ^{[1
]}

Merschaert, Alain ^{[1
]}

Delbeke, Pieter ^{[1
]}

Brione, Willy ^{[1
]}

机构：

[1] Eli Lilly & Co, Lilly Dev Ctr SA, Chem Prod Res & Dev & Analyt Sci Res & Dev, B-1348 Louvain, Belgium

来源：

ORGANIC PROCESS RESEARCH & DEVELOPMENT | 2007年 / 11卷 / 04期

关键词：

D O I：

10.1021/op060249m

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

We report herein a short and efficient synthesis of (RR)-2methyleyclopropanecarboxylic acid via a Horner-Wadsworth-Emmons reaction involving commercially available (S)-propylene oxide and triethylphosphonoacetate (TEPA). The TEPA/ base/propylene oxide stoichiometry was found critical to achieve high yields. We therefore studied the TEPA anion formation and stability using in situ IR spectroscopy. The reaction yield is strongly influenced by the counterion and solvent, whereas high diastereoselectivities are always obtained. Under the best experimental conditions (HexLi/MeTHF/150 degrees C), crude (RR)2-methylcyclopropanecarboxylic acid is obtained in 85-90% yield with > 98% trans selectivity.

引用

页码：689 / 692

页数：4

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