منابع مشابه
New samarium diiodide-induced cyclizations*
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...
متن کاملDynamic ligand exchange in reactions of samarium diiodide.
Mechanistic studies show the importance of iodide displacement by additives that accelerate reactions of samarium diiodide. The key feature important for acceleration of reaction rate is the use of proton donors and other additives that have a high enough affinity for Sm(II) to displace iodide yet do not saturate the coordination sphere inhibiting substrate reduction.
متن کاملHighly substituted benzannulated cyclooctanol derivatives by samarium diiodide-induced cyclizations
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...
متن کاملA novel reductive cyclization of arylmethylidenemalononitrile promoted by samarium diiodide
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...
متن کاملPhthalimides as exceptionally efficient single electron transfer acceptors in reductive coupling reactions promoted by samarium diiodide.
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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ژورنال
عنوان ژورنال: Synlett
سال: 2001
ISSN: 0936-5214,1437-2096
DOI: 10.1055/s-2001-16801