New Organolithium Addition Methodology to Diversely Functionalized Indoles
Claire M. Coleman and Donal F. O'Shea*
*Centre for Synthesis and Chemical Biology, Conway Institute, Department of Chemistry, University College Dublin, Belfield, Dublin 4, Ireland, Email: donal.f.osheaucd.ie
C. M. Coleman, D. F. O'Shea, J. Am. Chem. Soc., 2003, 125, 4054-4055.
DOI: 10.1021/ja034283h (free Supporting Information)
The reaction of Boc-protected ortho-aminostyrenes with alkyllithiums, followed by the addition of specific electrophiles sets up a cascade reaction process between the reacted electrophile and the ortho-amino substituent, facilitating an in situ ring closure and dehydration to generate an indole ring system.
see article for more examples
Indole Synthesis by Controlled Carbolithiation of o-Aminostyrenes
A. Kessler, C. M. Coleman, P. Charoenying, D. F. O'Shea, J. Org. Chem., 2004, 69, 7836-7846.