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Aldol reactions belong to the most frequently used C-C bond forming transformations utilized particularly for the construction of complex structures. The selectivity of these reactions depends on the geometry of the intermediate enolates. Here, we have reacted octyl pentafluoro-λ 6 -sulfanylacetate with substituted benzaldehydes and acetaldehyde under the conditions of the silicon-mediated Mukaiyama aldol reaction. The transformations proceeded with high diastereoselectivity. In case of benzaldehydes with electron-withdrawing substituents in the para -position, syn -α-SF 5 -β-hydroxyalkanoic acid esters were produced. The reaction was also successful with meta -substituted benzaldehydes and o -fluorobenzaldehyde. In contrast, p -methyl-, p -methoxy-, and p -ethoxybenzaldehydes led selectively to aldol condensation products with ( E )-configured double bonds in 30-40% yields. In preliminary experiments with an SF 5 -substituted acetic acid morpholide and p -nitrobenzaldehyde, a low amount of an aldol product was formed under similar conditions.

Syn-selective silicon Mukaiyama-type aldol reactions of (pentafluoro-λ6-sulfanyl)acetic acid esters with aldehydes

Syn-selective silicon Mukaiyama-type aldol reactions of (pentafluoro-λ⁶-sulfanyl)acetic acid esters with aldehydes