Glyoxylate-ene reaction catalyzed by Ln(OTf)3

Tetrahedron Letters

Volumn 38, Issue 38, 1997, Pages 6721-6724

  Qian, Changtao ^a   Huang, Taisheng ^a  

^a SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE DERIVATIVE; GLYOXYLIC ACID DERIVATIVE; LANTHANIDE;

ARTICLE; CATALYSIS; CHEMICAL REACTION; REACTION ANALYSIS;

EID: 0030865753     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)01536-0     Document Type: Article

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18. 3 can be almost quantitatively recovered from the aqueous layer and can be reused.
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21. 3 ( 0.2mmol) and (S)-6,6'-dibromo-binaphthol (0.24mmol) was added dichloromethane (2ml) at 0°C and the mixture was stirred for 0.5h at the same temperature. Methyl glyoxylate (1mmol) and α-methyl styrene (1.2mmol) were successively added at 0°C , and the mixture was stirred for 24h. Water was then added to quench the reaction. After usual work up, the crude product was puried by silica gel column chromatography to afford the desired ene adduct (78% yield, 38%ee).
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