Amine-catalyzed coupling of aldehydes and ketenes derived from Fischer carbene complexes: formation of beta-lactones and enol ethers.
Aldehydes react with ketenes generated from photolysis of Fischer chromium carbene complexes to generate either beta-lactones or enol ethers resulting from decarboxylation of beta-lactones. The reaction is catalyzed by tertiary amines and can occur with diastereoselectivity greater than 20:1 with DMAP as the catalyst.
Merlic
Craig A
CA
Department of Chemistry and Biochemistry, University of California, Los Angeles, 607 Charles Young Drive, Los Angeles, California 90095-1569, USA. merlic@chem.ucla.edu
Doroh
Brandon C
BC
D000447:Aldehydes / Q000737:chemistry*; D000588:Amines; D002384:Catalysis; D005030:Ethylenes / Q000737:chemistry*; D007202:Indicators and Reagents; D007659:Ketones / Q000737:chemistry*; D007783:Lactones / Q000138:chemical synthesis*; D009682:Magnetic Resonance Spectroscopy; D008958:Models, Molecular
D000447:Aldehydes; D000588:Amines; D005030:Ethylenes; D007202:Indicators and Reagents; D007659:Ketones; D007783:Lactones; C008223:ketene