3-BROMO-2-FLUOROPROPENE - A FLUORINATED BUILDING-BLOCK - 2-FLUOROALLYLATION OF GLYCINE AND ALANINE ESTER IMINES

Authors
LAUE KW HAUFE G
Citation
Kw. Laue et G. Haufe, 3-BROMO-2-FLUOROPROPENE - A FLUORINATED BUILDING-BLOCK - 2-FLUOROALLYLATION OF GLYCINE AND ALANINE ESTER IMINES, Synthesis, (10), 1998, pp. 1453-1456
Citations number
27
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Synthesis → ACNP
ISSN journal
00397881
Issue
10
Year of publication
1998
Pages
1453 - 1456
Database
ISI
SICI code
0039-7881(1998):10<1453:3-AFB->2.0.ZU;2-E
Abstract
3-Bromo-2-fluoropropene (4) is prepared in a new three-step synthesis from ammonium alpha-fluoroacrylate (1) in 31% overall yield. Glycine a nd alanine ester imines are efficiently alkylated by 4 to give, after deprotection, 2-amino-4-fluoropent-4-enoic acid (9) in 63% overall yie ld, and the alpha-methylated derivative 13 in 26% overall yield, respe ctively. Preliminary results indicate that 4 is potentially a new alph a-carbonyl cation equivalent.