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Volumn , Issue 13, 2009, Pages 2089-2092

Scope and limitations of samarium diiodide induced cyclizations of alkenyl-substituted γ-keto esters to benzannulated cyclooctanol derivatives

(2) Saadi, Jakub a Reissig, Hans Ulrich a

a FREIE UNIVERSITÄT BERLIN (Germany)

Author keywords

Cyclizations; Cycloheptanols; Cyclooctanols; Ketyl; Medium sized rings; Radical reactions; Samarium diiodide

Indexed keywords

5,7 DIMETHYL 1,5,6,7 TETRAHYDRO 2,5 METHANO 4 BENZOXONIN 3 (2H) ONE; ALKENYL GROUP; CARBONYL DERIVATIVE; CYCLOHEPTANE DERIVATIVE; CYCLOOCTANE DERIVATIVE; ESTER; METHYL 8 HYDROXY 8,10 DIMETHYL 5,6,7,8,9,10 HEXAHYDROBENZO[8] ANNULENE 6 CARBOXYLATE; SAMARIUM DIIODIDE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CYCLIZATION; STEREOCHEMISTRY; SUBSTITUTION REACTION;

EID: 68949146106 PISSN: 09365214 EISSN: 14372096 Source Type: Journal
DOI: 10.1055/s-0029-1217520 Document Type: Article

Times cited : (13)

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- Typical Procedure for SmI2-Induced Cyclizations, Conversion of 5 into 14 and 15 Samarium metal (278 mg, 1.85 mmol) and 1,2-diiodoethane (477 mg, 1.69 mmol) were placed under a flow of argon in a flame-dried, two-necked round-bottomed flask containing a magnetic stirring bar and a septum inlet. THF (20 mL) was added, and the mixture was vigorously stirred at r.t. for 2 h. HMPA (2.40 mL, 13.8 mmol) was added to this solution of SmI2, and after 10 min of stirring a solution of substrate 5 (200 mg, 0.77 mmol) and t-BuOH (146 μL, 1.54 mmol) in THF (31 mL) was added over 2 h. The mixture was stirred at r.t. for 16 h and quenched with sat. aq NaHCO3 solution (20 mL, The phases were separated and the aqueous layer was extracted with Et2O (3 × 25 mL, The combined organic layers were washed with H2O (10 mL) and brine (10 mL) and dried Na2SO4, The products were purified by column chroma
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