ArticleThe Journal of organic chemistry2026
[1,2]-Carbon to Carbon Silyl Migration for Accessing α-Silyl Alkanals from α-Hydroxy Allyl Silanes.
Article in The Journal of organic chemistry, 2026. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Not yet cited in PubMed.
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Abstract
An acid-catalyzed [1,2]-carbon-to-carbon silyl migration is reported for the synthesis of α-silyl aldehydes from α-hydroxy allyl silanes, which can serve as valuable precursors for various organic reactions. During the synthesis of α-hydroxy allyl silanes, an unexpected aldehyde peak in NMR suggested an in situ rearrangement, later confirmed to be acid-driven. Expanding the substrate scope revealed that an alkyl substituent at the β-position was crucial for migration. Mechanistic studies indicated a stepwise process via a carbocation intermediate, as confirmed by stereochemical erosion in enantiomerically enriched substrates. The tertiary carbocation is further stabilized by the β-silicon effect. The advantages of this method include mild reaction conditions, clean conversion, and often no need for purification.
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