Samarium diiodide-induced reductive coupling of chiral nitrones with methyl acrylate
نویسندگان
چکیده
منابع مشابه
A new approach to 3-hydroxyprolinol derivatives by samarium diiodide-mediated reductive coupling of chiral nitrone with carbonyl compounds.
A flexible diastereoselective approach to trans-(3S)-hydroxyprolinol derivatives is described, which is based on the samarium diiodide-mediated reductive coupling of the chiral 1-pyrroline N-oxide (nitrone)(S)-10 with carbonyl compounds. The reductive hydroxyalkylation of nitrone 10 with ketones and aromatic aldehydes is highly diastereoselective in establishing the C-2 chiral center of the pyr...
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Samarium diiodide (SmI2) smoothly promotes the cyclizations of suitably substituted carbonyl compounds with styrene subunits leading to benzannulated cyclooctenes. The intramolecular samarium ketyl addition to arene or hetarene moieties enables a new, efficient, and highly stereoselective entry to dearomatized products such as hexahydronaphthalenes, steroid-like tetraor pentacyclic compounds, o...
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Experimental and theoretical evidence shows that phthalimides are highly efficient single electron transfer acceptors in reactions promoted by samarium diiodide, affording ketyl radical anion intermediates, which participate in high-yielding inter- and intramolecular reductive coupling processes with different radicophiles including imides, oxime ethers, nitrones, and Michael acceptors.
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Carbon]carbon bond formation is the essence of organic synthesis and the reductive dimerization of carbonyl derivatives is a most valuable method for establishing carbon]carbon bonds. Since the time Kagan demonstrated a simple preparation of samarium diiodide from samarium metal and 1,2-diiodoethane, SmI2 has been developed as a mild, neutral and versatile single electron transfer reductant. It...
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A series of γ-oxo esters suitably substituted with various styrene subunits was subjected to samarium diiodide-induced 8-endo-trig cyclizations. Efficacy, regioselectivity and stereoselectivity of these reactions via samarium ketyls strongly depend on the substitution pattern of the attacked alkene moiety. The stereoselectivity of the protonation of the intermediate samariumorganyl is also infl...
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ژورنال
عنوان ژورنال: Arkivoc
سال: 2007
ISSN: 1551-7012
DOI: 10.3998/ark.5550190.0009.803