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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*a
a 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 (online)

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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.

Key words

thiourea - hydrogen-bond donor - planar-chiral - cross-coupling

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Compound 7c was reported by Ma and co-workers; see ref. 6c.

13

CCDC 775030 contains the supplementary crystallographic data for this paper. These data can be obtained free of charge at www.ccdc.cam.ac.uk/conts/retrieving.html [or from the Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge CB2 1EZ, UK; fax: +44(1223)336033, E-mail: deposit@ccdc.cam.ac.uk].