This reaction is useful for the stereoselective synthesis of α,β-unsaturated ketones. The reaction involves the condensation of a phosphonate (containing the heteroatom) with an aldehyde or ketone, followed by a base-catalyzed elimination to form the α,β-unsaturated ketone. The stereochemistry of the product can be controlled through the choice of the starting materials and reaction conditions.
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(Z)-4-Methoxy-1-phenyl-2-trimethylsilanyl-but-2-en-1-one
2,3,4,6-tetra-O-benzyl-5-[N-(tert-butoxycarbonyl)amino]-5-deoxy-α-D-galactopyranosyl-(2S,3S,4R)-2-azido-3,4-di-O-benzyloctadecane-1,3,4-triol
