Formal Cycloaddition of Disubstituted Ketenes with 2-Oxoaldehydes Catalyzed by Chiral N-Heterocyclic Carbenes

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 β-lactones with α-quaternary-β-tertiary stereocenters in high yields with good diastereoselectivities and excellent enantioselectivi...

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Veröffentlicht in:	Journal of organic chemistry 2008-10, Vol.73 (20), p.8101-8103
Hauptverfasser:	He, Lin, Lv, Hui, Zhang, Yan-Rong, Ye, Song
Format:	Artikel
Sprache:	eng
Schlagworte:	Aldehydes - chemistry Catalysis Catalysts: preparations and properties Chemistry Ethylenes - chemistry Exact sciences and technology General and physical chemistry Heterocyclic compounds Heterocyclic compounds with o, s, se, te hetero atom and condensed derivatives Ketones - chemistry Methane - analogs & derivatives Methane - chemistry Organic chemistry Preparations and properties Stereoisomerism Theory of reactions, general kinetics. Catalysis. Nomenclature, chemical documentation, computer chemistry
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Beschreibung
Zusammenfassung:	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 β-lactones with α-quaternary-β-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.
ISSN:	0022-3263 1520-6904
DOI:	10.1021/jo801494f