The right mix! When one considers the many ways in which a polyfunctional organometallic species may be quenched before any productive CC bond formation can occur (two amide protons, five esters), the samarium-promoted coupling between sulfide 1 and aldehyde 2 is remarkably efficient (see scheme). This is shown in the synthesis of a stable mimic of the sialylTn (Tn=GalNAcα1→O-Ser/Thr) disaccharide.
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Abdallah et al. (2003) studied this question.
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