Tetrahedron Letters

A new approach to the synthesis of (Z)-2-fluoro-2-alkenals via Wittig-type carbonyl condensation reactions of 2-(fluoromethyl)-4, 4, 6-trimethyl-1, 3-oxazine …

M Kajjout, M Smietana, J Leroy, C Rolando

Index: Kajjout, Mohammed; Smietana, Michael; Leroy, Jacques; Rolando, Christian Tetrahedron Letters, 2013 , vol. 54, # 13 p. 1658 - 1660

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Citation Number: 5

Abstract

We report here the transformation of aldehydes to their (Z)-α-fluoro-α, β-unsaturated aldehyde homologs by condensation with the phosphonium salt of the Meyer's oxazine obtained from bromofluoroacetonitrile. After methylation with trimethyloxonium tetrafluoroborate the quaternized oxazine is cleanly reduced to mostly Z 2-fluoro-2-alkenals by sodium borohydride at room temperature. This methodology is compatible with usual ...