Literature DB >> 11777441

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

R Ocampo1, W R Dolbier, K A Abboud, F Zuluaga.   

Abstract

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.

Entities:  

Year:  2002        PMID： 11777441     DOI： 10.1021/jo015778x

Source DB:  PubMed          Journal:  J Org Chem        ISSN： 0022-3263            Impact factor:   4.354


  3 in total

1.  Chemoenzymatic synthesis of each enantiomer of orthogonally protected 4,4-difluoroglutamic acid: a candidate monomer for chiral Brønsted acid peptide-based catalysts.

Authors:  Yang Li; Scott J Miller
Journal:  J Org Chem       Date:  2011-11-09       Impact factor: 4.354

2.  Engineering site-selective incorporation of fluorine into polyketides.

Authors:  Sasilada Sirirungruang; Omer Ad; Thomas M Privalsky; Swetha Ramesh; Joel L Sax; Hongjun Dong; Edward E K Baidoo; Bashar Amer; Chaitan Khosla; Michelle C Y Chang
Journal:  Nat Chem Biol       Date:  2022-07-11       Impact factor: 16.174

3.  An Enantio- and Diastereoselective Chemoenzymatic Synthesis of α-Fluoro β-Hydroxy Carboxylic Esters.

Authors:  James K Howard; Marion Müller; Alan Berry; Adam Nelson
Journal:  Angew Chem Int Ed Engl       Date:  2016-04-19       Impact factor: 15.336
  3 in total

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