Catalytic asymmetric acyl halide-aldehyde cyclocondensation reactions of substituted ketenes.
Catalytic asymmetric acyl halide-aldehyde cyclocondensation (AAC) reactions of alkyl-substituted ketenes with structurally diverse aldehydes provide cis-disubstituted beta-lactones with high enantioselectivity. The AAC reactions utilize a novel Al(III)-triamine catalyst in which the metal's dynamic coordination geometry leads to a highly selective catalyst complex. These AAC reactions represent a functional solution to highly enantioselective substituted ester enolate aldol additions.
Nelson
Scott G
SG
Department of Chemistry, University of Pittsburgh, Pittsburgh, Pennsylvania 15260, USA. sgnelson@pitt.edu
Zhu
Cheng
C
Shen
Xiaoqiang
X
D000447:Aldehydes / Q000737:chemistry*; D002384:Catalysis; D003500:Cyclization; D006842:Hydrocarbons, Brominated / Q000737:chemistry*; D007659:Ketones / Q000737:chemistry; D007783:Lactones / Q000138:chemical synthesis*; D008958:Models, Molecular
D000447:Aldehydes; D006842:Hydrocarbons, Brominated; D007659:Ketones; D007783:Lactones