Enantioselective allylation of aldehydes promoted by chiral sulfur reagents

Tetrahedron Letters

Volumn 47, Issue 11, 2006, Pages 1829-1831

  Melo, Rosanne P A ^a   Vale, Juliana A ^a   Zeni, Gilson ^b   Menezes, Paulo H ^a  

^a DEPARTAMENTO DE QUÍMICA FUNDAMENTAL   (Brazil)

^b FEDERAL UNIVERSITY OF SANTA MARIA   (Brazil)

Author keywords

Allylation; Chiral sulfur reagents; Enantioselective addition; Lewis base catalysis

Indexed keywords

ALDEHYDE DERIVATIVE; BROMINE DERIVATIVE; SULFUR DERIVATIVE;

ADDITION REACTION; ALLYLATION; ARTICLE; CATALYST; CHIRALITY; ENANTIOSELECTIVITY;

EID: 32244444343     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2006.01.014     Document Type: Article

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25. Representative procedure for the asymmetric allylation of aldehydes: Zinc (100 mg; 1.5 mmol) in anhydrous THF was activated successively with 1,2-dibromoethane and chlorotrimethylsilane, which were stirred under argon for 5 min. Allyl bromide (0.14 mL; 1.35 mmol) was added at -78°C and the mixture was stirred for 10 min. Chiral ligand (0.5 mol %) in THF was then added at -78°C and stirred for 10 min, followed by aldehyde (1.2 mmol) addition at -78°C. The reaction mixture was allowed to warm to room temperature and was then quenched by the addition of HCl (0.1 M). The mixture was then extracted with AcOEt (2 × 10 mL) and the organic layer was dried over anhydrous magnesium sulfate, filtered, and concentrated in vacuo. The crude product was purified by chromatography using silica gel to yield the desired homoallylic alcohols.
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