Revisiting the aldol reaction of cis-α,β-epoxyaldehyde promoted by BF(3)·Et(2)O: direct access to 2-deoxy-2-fluoro heptulosonic ester analogues.
The aldol reaction between cis-3-((tert-butyldiphenylsilyloxy)methyl)oxirane-2-carbaldehyde and ethyl-2-(trimethylsilyloxy)-2-propenoate promoted by boron trifluoride diethyl etherate was reinvestigated. By varying the work-up conditions, a new 2-deoxy-2-fluoro heptulosonic ester analogue was synthesized. Derivatizations and detailed NMR analysis allowed the complete characterization of this fluoro analogue and its derivatives.
Laboratoire de Synthèse et Physicochimie de Molécules d'Intérêt Biologique, UMR-CNRS 5068, Université Paul Sabatier, 31062 Toulouse, Cedex 9, France.
Hatim
H
Filali
Mathieu
M
Danel
Stéphanie
S
Ballereau
Michel
M
Baltas
D000179:Acrylates / Q000737:chemistry*; D000447:Aldehydes / Q000737:chemistry*; D001880:Boranes / Q000737:chemistry*; D002384:Catalysis; D004852:Epoxy Compounds / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D017646:Organosilicon Compounds / Q000737:chemistry*
D000179:Acrylates; D000447:Aldehydes; D001880:Boranes; D004852:Epoxy Compounds; D017646:Organosilicon Compounds; C101707:boron trifluoride etherate