A Short Olefin Metathesis Based Route to Enantiomerically Pure Arylated Dihydropyrans and α,β‐Unsaturated δ‐Valero Lactones.

Wildemann, Holger; Duenkelmann, Pascal; Mueller, Michael; Schmidt, Bernd

doi:10.1002/chin.200325149

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2021

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“…6e). The high diastereoselectivity of compound 20 may originate from the chelation of hydroxyl, carbonyl oxygen, and magnesium 86 .…”

Section: Resultsmentioning

confidence: 99%

Passerini-type reaction of boronic acids enables α-hydroxyketones synthesis

et al. 2021

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Multicomponent reactions (MCRs) facilitate the rapid and diverse construction of molecular scaffolds with modularity and step economy. In this work, engagement of boronic acids as carbon nucleophiles culminates in a Passerini-type three-component coupling reaction towards the synthesis of an expanded inventory of α-hydroxyketones with skeletal diversity. In addition to the appealing features of MCRs, this protocol portrays good functional group tolerance, broad substrate scope under mild conditions and operational simplicity. The utility of this chemistry is further demonstrated by amenable modifications of bioactive products and pharmaceuticals as well as in the functionalization of products to useful compounds.

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“…6e). The high diastereoselectivity of compound 20 may originate from the chelation of hydroxyl, carbonyl oxygen, and magnesium 86 .…”

Section: Resultsmentioning

confidence: 99%