Indium-mediated regio- and chemoselective synthesis of alpha-hydroxyalkyl allenic esters and gold-catalyzed cyclizations to ethyl 2-naphthoate derivatives.
The regio- and chemoselective synthetic method of functionalized alpha-hydroxyalkyl allenic esters was developed from the reactions of various aldehydes with organoindium reagent generated in situ from indium and ethyl 4-bromobutynoate. The alpha-hydroxyalkyl allenic esters possessing electron-donating groups were cyclized to ethyl 2-naphthoate derivatives through intramolecular C-alkylation catalyzed by gold salts.
Park
Chansoo
C
National Research Laboratory for Catalytic Organic Reaction, Department of Chemistry, Kangwon National University, Chunchon 200-701, Republic of Korea.
Lee
Phil Ho
PH
D000447:Aldehydes / Q000737:chemistry; D000466:Alkadienes / Q000138:chemical synthesis* / Q000737:chemistry; D000478:Alkylation; D000480:Alkynes / Q000737:chemistry; D002384:Catalysis; D003500:Cyclization; D004952:Esters / Q000138:chemical synthesis / Q000737:chemistry; D006046:Gold / Q000737:chemistry*; D007204:Indium / Q000737:chemistry*; D009284:Naphthols / Q000138:chemical synthesis* / Q000737:chemistry
D000447:Aldehydes; D000466:Alkadienes; D000480:Alkynes; D004952:Esters; D009284:Naphthols; D007204:Indium; C025947:propadiene; D006046:Gold