Cyclization into Hydrindanes Using Samarium Diiodide: Stereochemical Features Depending on the Protecting Group
نویسندگان
چکیده
منابع مشابه
A 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...
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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...
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 کاملCyclizations producing hydrindanones with two methyl groups at the juncture positions mediated by samarium diiodide and electrolysis.
One-electron reductive intramolecular cyclization of enones with ketones or aldehydes mediated by samarium diiodide and electrolysis to afford cis-trimethyl- hydrindanolones. The reactions gave selectivities ranging from 1:1 to 100:0 depending on the conditions.
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ژورنال
عنوان ژورنال: Natural Product Communications
سال: 2016
ISSN: 1934-578X,1555-9475
DOI: 10.1177/1934578x1601100807