Umpolung reactivity of difluoroenol silyl ethers with amines and amino alcohols.: Application to the synthesis of enantiopure α-difluoromethyl amines and amino acids

被引：34

作者：

Huguenot, Florent ^{[1
]}

Billac, Anne ^{[1
]}

Brigaud, Thierry ^{[2
]}

Portella, Charles ^{[1
]}

机构：

[1] Univ Reims, Fac Sci, UMR 6229, CNRS,Inst Chim Mol Reims, F-51687 Reims 2, France

[2] Univ Cergy Pontoise, CNRS, UMR 8123, Lab SOSCO, F-95031 Neuville Sur Oise, Cergy Pontoise, France

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2008年 / 73卷 / 07期

关键词：

D O I：

10.1021/jo702328v

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Difluoroenol silyl ethers, produced in situ from acylsilanes and CF3TMS, react as electrophiles with amines to give difluoroimines, via the corresponding hemiaminal adduct, as evidenced by F-19 NMR spectroscopy. Reaction with (R)-phenylglycinol led to 2-difluoromethyloxazolidines. After separation of the diastereomers, reduction with LAH and Strecker-type synthesis gave enantiopure alpha-difluoromethy-lamines and alpha-difluoromethyl-alpha-amino acids, respectively.

引用

页码：2564 / 2569

页数：6

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