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.
Filali
Hatim
H
Laboratoire de Synthèse et Physicochimie de Molécules d'Intérêt Biologique, UMR-CNRS 5068, Université Paul Sabatier, 31062 Toulouse, Cedex 9, France.
Danel
Mathieu
M
Ballereau
Stéphanie
S
Baltas
Michel
M
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