Synthesis 2012(3): 409-416  
DOI: 10.1055/s-0031-1289656
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Synthetic Approaches to Highly Functional β-Carboline Building Blocks via Allylic Amidation

Johannes F. Teichert, Martín Fañanás-Mastral, Ben L. Feringa*Stratingh Institute for Chemistry, University of Groningen, Nijenborgh 4, 9747 AG, Groningen, The Netherlands
Fax: +31(50)3634296; e-Mail: b.l.feringa@rug.nl;
Further Information

Publication History

Received 7 November 2011
Publication Date:
22 December 2011 (eFirst)

Abstract

A new, straightforward synthesis of highly functional β-carboline building blocks is presented that makes use of allylic amidation methodology. The products obtained carry a terminal double bond as well as an easy-to-deprotect amide, which make them perfectly suitable for further functionalization. The use of the trifluoroacetamide group is exploited in a dual fashion; it acts as a protecting group and functions as the nucleophile for the allylic amidation reaction.