Highly diastereoselective 7-endo radical cyclization of ethyl α-methylene-γ-(bromomethyl)dimethylsiloxycarboxylates

Tetrahedron Letters

Volumn 45, Issue 22, 2004, Pages 4329-4332

  Nagano, Hajime ^a   Hara, Saori ^a  

^a OCHANOMIZU UNIVERSITY   (Japan)

Author keywords

Silyl radical; 1,3 Asymmetric induction; Radical reaction; Solvent effect

Indexed keywords

ALCOHOL DERIVATIVE; ALKYL GROUP; CARBONYL DERIVATIVE; CARBOXYLIC ACID DERIVATIVE; ETHER DERIVATIVE; PROPANE; TETRAHYDROFURAN;

ARTICLE; CHEMICAL MODIFICATION; CYCLIZATION; DIASTEREOISOMER; ENANTIOSELECTIVITY; OXIDATION; QUANTUM YIELD; RADICAL REACTION; REDUCTION KINETICS; STEREOCHEMISTRY;

EID: 2342497739     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2004.03.188     Document Type: Article

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40. Typical procedure: A solution of the crude cyclization product 6d prepared from 5d (88 mg, 0.26 mmol) in hexane was put on a silica gel column and allowed to stand at room temperature for 1 h. Elution with hexane and then with hexane-ethyl acetate (1:1) gave 11d (60 mg, 83% yield). Yields: 11a (94%); 11b (92%); 11c (conversion yield 91%); 11e (95%); 11f (90%)
41. Yields: 12a (85%); 12d (95%); 12e (87%); 12f (95%); 13a (80%); 13d (80%); 13e (81%); 13f (conversion yield 87%)