One-step assembly of functionalized γ-butyrolactones from benzoins or benzaldehydes via an N-heterocyclic carbene-mediated tandem reaction

Organic Letters

Volumn 7, Issue 17, 2005, Pages 3769-3771

  Ye, Wei ^a,b   Cai, Guanliang ^b   Zhuang, Zeyang ^a,c   Jia, Xueshun ^c   Zhai, Hongbin ^a  

^a SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

^b RESEARCH INSTITUTE OF CHEMICAL DEFENSE   (China)

^c SHANGHAI UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

BENZALDEHYDE DERIVATIVE; BENZOIN; CARBENE; DRUG DERIVATIVE; GAMMA BUTYROLACTONE; HYDROCARBON; METHANE;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; SYNTHESIS;

4-BUTYROLACTONE; BENZALDEHYDES; BENZOIN; CATALYSIS; HYDROCARBONS; METHANE; MOLECULAR STRUCTURE;

EID: 24044495219     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol051422m     Document Type: Article

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29. (iii) Burstein, C.; Glorius, F. Angew. Chem., Int. Ed. 2004, 43, 6205]. Then, 4 Å MS (500 mg), benzoin (1 mmol), and methyl acrylate (1.8 mL, 20 mmol) were added, and the resulting mixture was stirred for the indicated time. The reaction mixture was passed through a short pad of Celite, and the solvent was evaporated under reduced pressure to afford a residue that was purified by flash column chromatography on silica gel to give the product.
30. 2 for 45 min. Benzaldehyde (1.0 mmol) was added, and the resulting mixture was stirred for 3 h. Then, 4 A MS (500 mg) and methyl acrylate (0.90 mL, 10 mmol) were added, and the reaction mixture was stirred for the indicated time. The reaction mixture was passed through a short pad of Celite, and the solvent was evaporated under reduced pressure to afford a residue that was purified by flash column chromatography on silica gel to give the product.