Journal of Organic Chemistry 2002-01-11

Catalyzed Reformatsky reactions with ethyl bromofluoroacetate for the synthesis of alpha-fluoro-beta-hydroxy acids.

R Ocampo, W R Dolbier, K A Abboud, F Zuluaga

文献索引：J. Org. Chem. 67(1) , 72-8, (2002)

全文：HTML全文

摘要

The presence of catalytic amounts of CeCl(3) improves yields and simplifies procedure in the Reformatsky reactions of ethyl bromofluoroacetate with aldehydes and ketones to generate diastereomeric mixtures of alpha-fluoro-beta-hydroxy esters, some of which can be separated by crystallization or column flash chromatography. Diastereomerically pure alpha-fluoro-beta-hydroxy acids are obtained by mild alkaline hydrolysis of the resolved alpha-fluoro-beta-hydroxy esters. Detailed NMR data of new alpha-fluoro-beta-hydroxy esters and alpha-fluoro-beta-hydroxy acids are also presented.

相关化合物

  • 溴氟乙酸乙酯

相关文献：

Visible-light-mediated fluoroalkylation of isocyanides with ethyl bromofluoroacetates: unified synthesis of mono- and difluoromethylated phenanthridine derivatives.

2014-06-06

[Org. Lett. 16(11) , 2938-41, (2014)]

A straightforward and highly diastereoselective access to functionalized monofluorinated cyclopropanes via a Michael initiated ring closure reaction.

2013-11-01

[Org. Lett. 15(21) , 5598-601, (2013)]

[J. Fluor. Chem. 77 , 45, (1996)]

[J. Chem. Soc. Perkin Trans. I , 49, (1991)]

Synthesis of (E)-and (Z)-fluoro-olefin analogues of potent dipeptidyl peptidase IV inhibitors. Van der Veken P, et al.

[Tetrahedron Lett. 44(33) , 6231-34, (2003)]

更多文献...