Synthesis 2012; 44(17): 2793-2797
DOI: 10.1055/s-0032-1316755
paper
© Georg Thieme Verlag Stuttgart · New York

Synthesis of Josiphos-Type Bisphospholane Ligands

Tim Hammerer
a   Institut für Technische Chemie und Makromolekulare Chemie, RWTH Aachen University, Worringerweg 1, 52074 Aachen, Germany, Fax: +49(241)8022177   eMail: francio@itmc.rwth-aachen.de   eMail: leitner@itmc.rwth-aachen.de
,
Andrea Dämbkes
a   Institut für Technische Chemie und Makromolekulare Chemie, RWTH Aachen University, Worringerweg 1, 52074 Aachen, Germany, Fax: +49(241)8022177   eMail: francio@itmc.rwth-aachen.de   eMail: leitner@itmc.rwth-aachen.de
,
Wolfgang Braun
b   Institut für Anorganische Chemie, RWTH Aachen University, Landoldtweg 1, 52074 Aachen, Germany
,
Albrecht Salzer
b   Institut für Anorganische Chemie, RWTH Aachen University, Landoldtweg 1, 52074 Aachen, Germany
,
Giancarlo Franciò*
a   Institut für Technische Chemie und Makromolekulare Chemie, RWTH Aachen University, Worringerweg 1, 52074 Aachen, Germany, Fax: +49(241)8022177   eMail: francio@itmc.rwth-aachen.de   eMail: leitner@itmc.rwth-aachen.de
,
Walter Leitner*
a   Institut für Technische Chemie und Makromolekulare Chemie, RWTH Aachen University, Worringerweg 1, 52074 Aachen, Germany, Fax: +49(241)8022177   eMail: francio@itmc.rwth-aachen.de   eMail: leitner@itmc.rwth-aachen.de
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Publikationsverlauf

Received: 21. Mai 2012

Accepted after revision: 23. Juni 2012

Publikationsdatum:
01. August 2012 (online)


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Abstract

Bisphospholane Josiphos-type ligands were synthesized in high yields employing electrophilic and nucleophilic phospholane synthons. Full characterization data including solid-state structures of the diastereomeric ligands are reported. These ligands resulted in active and enantioselective iridium catalysts for the asymmetric hydrogenation of imines. Pronounced cooperative effects of the chiral elements within the ligand structure were observed and enantioselectivities of up to 74% ee were achieved.