Article

Catalytic enantioselective 1,3-dipolar cycloadditions of alkyl diazoacetates with alpha,beta-disubstituted acroleins.

Department of Chemistry, Sungkyunkwan University, Suwon 440-746, Korea.
Chemical Communications (impact factor: 6.17). 10/2009; DOI:10.1039/b910321j pp.5460-2
Source: PubMed

ABSTRACT A catalytic route to highly functionalized chiral 2-pyrazolines by an asymmetric 1,3-dipolar cycloaddition reaction of ethyl diazoacetate with alpha-substituted and alpha,beta-disubstituted acroleins has been developed; in the presence of chiral (S)-oxazaborolidinium ion as catalyst, the reaction proceeded with high to excellent enantioselectivities (up to 99% ee).

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Keywords

asymmetric 1,3-dipolar cycloaddition reaction
 
catalytic route
 
ethyl diazoacetate
 
excellent enantioselectivities
 
functionalized chiral 2-pyrazolines
 
reaction proceeded
 
S)-oxazaborolidinium ion
 

Lizhu Gao