Domino process in silver-catalyzed reactions of N-arylformimidates and active methylene compounds involving cycloisomerization and 1,3-alkenyl shift.
We have developed an efficient method for the synthesis of 2,3-disubstituted indoles from alkyne iminoethers 1 that employs a domino process involving Ag-catalyzed condensation followed by a tandem Ag-induced cycloisomerization and 1,3-alkenyl shift to Ag-activated carbon. This methodology can be useful in regioselectively constructing 3-alkylated indoles, which are part of the structures of biologically active compounds and important alkaloids.
Oh
Chang Ho
CH
Department of Chemistry, Hanyang University, Sungdong-Gu, Seoul 133-791, Korea. changho@hanyang.ac.kr
Karmakar
Swastik
S
Park
HyoSeung
H
Ahn
YoungCheon
Y
Kim
Jung Wook
JW
D000475:Alkenes / Q000737:chemistry*; D002384:Catalysis; D007096:Imidoesters / Q000737:chemistry*; D007211:Indoles / Q000737:chemistry; D007536:Isomerism; D012834:Silver / Q000737:chemistry*
D000475:Alkenes; D007096:Imidoesters; D007211:Indoles; D012834:Silver