Article

Catalytic asymmetric synthesis of trisubstituted aziridines.

Department of Chemistry, Michigan State University, East Lansing, Michigan 48824, USA.
Journal of the American Chemical Society (impact factor: 9.91). 06/2011; 133(23):8892-5. DOI:10.1021/ja203754p pp.8892-5
Source: PubMed

ABSTRACT A method is described which provides for the direct asymmetric catalytic synthesis of trisubstituted aziridines from imines and diazo compounds. While unactivated imines were not reactive to α-diazo carbonyl compounds in which the diazo carbon was disubstituted, N-Boc imines react with both α-diazo esters and α-diazo-N-acyloxazolidinones to give trisubstituted aziridines with excellent diastereo- and enantioselectivities.

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Keywords

diazo carbon
 
diazo compounds
 
direct asymmetric catalytic synthesis
 
enantioselectivities
 
trisubstituted aziridines
 
α-diazo carbonyl compounds
 
α-diazo esters
 

Li Huang