Matches in SemOpenAlex for { <https://semopenalex.org/work/W4362602528> ?p ?o ?g. }
- W4362602528 abstract "The first use of 1,4-pentadiene and 1,5-hexadiene as allylmetal pronucleophiles in regio-, anti-diastereo-, and enantioselective carbonyl addition from alcohol proelectrophiles is described. As corroborated by deuterium labeling experiments, primary alcohol dehydrogenation delivers a ruthenium hydride that affects alkene isomerization to furnish a conjugated diene, followed by transfer hydrogenative carbonyl addition. Hydrometalation appears to be assisted by the formation of a fluxional olefin-chelated homoallylic alkylruthenium complex II, which exists in equilibrium with its pentacoordinate η1 form to enable β-hydride elimination. This effect confers remarkable chemoselectivity: while 1,4-pentadiene and 1,5-hexadiene are competent pronucleophiles, higher 1,n-dienes are not, and the olefinic functional groups of the products remain intact under conditions in which the 1,4- and 1,5-dienes isomerize. A survey of halide counterions reveals iodide-bound ruthenium-JOSIPHOS catalysts are uniquely effective in these processes. This method was used to prepare a previously reported C1–C7 substructure of (−)-pironetin in 4 vs 12 steps." @default.
- W4362602528 created "2023-04-06" @default.
- W4362602528 creator A5017563754 @default.
- W4362602528 creator A5026099869 @default.
- W4362602528 creator A5042928999 @default.
- W4362602528 creator A5066220403 @default.
- W4362602528 date "2023-04-05" @default.
- W4362602528 modified "2023-10-16" @default.
- W4362602528 title "Dual Ruthenium-Catalyzed Alkene Isomerization–Hydrogen Auto-Transfer Unlocks Skipped Dienes as Pronucleophiles for Enantioselective Alcohol C–H Allylation" @default.
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- W4362602528 doi "https://doi.org/10.1021/jacs.3c00934" @default.
- W4362602528 hasPubMedId "https://pubmed.ncbi.nlm.nih.gov/37018070" @default.