Organic Chemistry Portal

Abstracts

Search:

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)


Abstract

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.

DOI: 10.1021/jo048723e


Key Words

Indoles, Deprotection


ID: J48-Y2003-1410