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2005
Ketones
Q 0350
31- 094
An Unexpected Highly Diastereoselective Double Baylis—Hillman Reaction of
Per- (or Poly)fluorophenyl Aromatic Aldimines with Methyl Vinyl Ketones. —
Double Baylis—Hillman adducts (IV) are formed exclusively in the anti-configuration
by use of DABCO as Lewis base and DMF as solvent. They are smoothly converted
into cyclohexenones. Using PPh3 as the base, the reaction of imines (I) with ketone (II)
in THF gives the normal Baylis—Hillman adducts (III) along with the double adducts
in varying ratios. If Michael acceptors (VII) react under the former conditions with imine (Ia), no double adducts are observed. A study of the reaction of fluorinated imines
(IX) with (II) shows that only derivative (IXa) forms a normal Baylis—Hillman adduct,
whereas (IXb)—(IXd) are not suitable for the applied conditions. — (LIU, X.; ZHAO,
J.; JIN, G.; ZHAO*, G.; ZHU, S.; WANG, S.; Tetrahedron 61 (2005) 15, 3841-3851;
State Key Lab. Organofluorine Chem., Shanghai Inst. Org. Chem., Chin. Acad. Sci.,
Shanghai 200032, Peop. Rep. China; Eng.) — Klein
2005
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