Formal Cycloaddition of Disubstituted Ketenes with 2-Oxoaldehydes Catalyzed by Chiral N-Heterocyclic Carbenes
The Journal of Organic Chemistry2008Vol. 73(20), pp. 8101–8103
Citations Over TimeTop 10% of 2008 papers
Abstract
Chiral N-hetereocyclic carbenes were found to be efficient catalysts for the formal [2 + 2] cycloaddition reactions of alkyl(aryl)ketenes with 2-oxoaldehydes to afford beta-lactones with alpha-quaternary-beta-tertiary stereocenters in high yields with good diastereoselectivities and excellent enantioselectivities (up to 99% ee). Both alkyl(aryl)ketenes and diarylketene worked well in this reaction.
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