Synthesis 2010(20): 3486-3492  
DOI: 10.1055/s-0030-1258205
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Synthesis of Enantiopure Planar-Chiral Thiourea Derivatives

Jakob F. Schneidera, Roland Fröhlichb, Jan Paradies*aa Institute for Organic Chemistry, Karlsruhe Institute of Technology, Fritz-Haber-Weg 6, 76131 Karlsruhe, Germany
Fax: +49(721)6085637; e-Mail: jan.paradies@kit.edu;
b Institute of Organic Chemistry, University of Münster, Corrensstrasse 40, 48149 Münster, Germany
Further Information

Publication History

Received 14 May 2010
Publication Date:
13 August 2010 (eFirst)

Abstract

An efficient access to enantiopure pseudo-geminally substituted 4-amino-13-bromo[2.2]paracyclophane is described. The aminobromide was employed in cross-coupling reactions to yield arylated 4-amino[2.2]paracyclophanes. The amines were converted into enantiopure planar-chiral thioureas, which are potential hydrogen-bond donors for enantioselective organocatalysis.