BINOL-Salen-catalyzed highly enantioselective alkyne additions to aromatic aldehydes

Organic Letters

Volumn 6, Issue 6, 2004, Pages 1065-1068

  Li, Zi Bo ^a   Pu, Lin ^a  

^a UNIVERSITY OF VIRGINIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE DERIVATIVE; ALKYNE;

ADDITION REACTION; ARTICLE; CATALYSIS; CATALYST; COOLING; ENANTIOSELECTIVITY; HEATING; ROOM TEMPERATURE;

ACETYLENE; ALDEHYDES; ALKYNES; CATALYSIS; CYCLIZATION; ETHYLENEDIAMINES; LIGANDS; MOLECULAR STRUCTURE; NAPHTHOLS; STEREOISOMERISM; ZINC;

EID: 1642487286     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0498139     Document Type: Article

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37. 2Zn (0.5 mmol) were added to a 10 mL flask containing toluene (1 mL, distilled over sodium). After the solution was stirred at room temperature for 1 h, ligand (-)-1 (0.054 mmol, 38.2 mg) was added and the mixture stirred for another 1 h. Then, an aldehyde (0.25 mmol) was added and the reaction was allowed to proceed at room temperature for 18 h. Water was added to quench the reaction, and the mixture was extracted with diethyl ether and dried with sodium sulfate. After column chromatography on silica gel eluted with 2-10% ethyl acetate in hexanes, the propargylic alcohol product was isolated. The enantiomeric purity of the product was determined by using HPLC Chiralcel OD column.