New organolithium addition methodology to diversely functionalized indoles.
A novel synthetic approach to diversely functionalized indoles is described. Boc-protected ortho-aminostyrenes undergo an alkyllithium addition reaction, thereby generating a lithiated intermediate, which upon reaction with specific electrophiles sets up a cascade reaction process between the reacted electrophile and ortho-amino substituent, facilitating an in situ ring closure, followed by dehydration, to generate an indole ring system. This methodology is demonstrated by the synthesis of a range of 3,5-, 1,3,5-, and 2,3,5-substituted indoles.
Coleman
Claire M
CM
Centre for Synthesis and Chemical Biology, Conway Institute, Department of Chemistry, University College Dublin, Belfield, Dublin 4, Ireland.
O'Shea
Donal F
DF
D007211:Indoles / Q000138:chemical synthesis*; D008094:Lithium / Q000737:chemistry*; D009942:Organometallic Compounds / Q000737:chemistry*; D013343:Styrenes / Q000737:chemistry
D007211:Indoles; D009942:Organometallic Compounds; D013343:Styrenes; D008094:Lithium