Synlett 2003(6): 0833-0836
DOI: 10.1055/s-2003-38740
LETTER
© Georg Thieme Verlag Stuttgart ˙ New York

Iridium-HetPHOX Complexes for the Catalytic Asymmetric Hydrogenation of Olefins and Imines

Pier Giorgio Cozzi*a, Frederik Mengesb, Stefan Kaiserb
a Dipartimento di Chimica , ‘G. Ciamician’, Via Selmi 2, 40126, Bologna, Italy
Fax: +39(51)2099456; e-Mail: pgcozzi@ciam.unibo.it;
b Department of Chemistry, University of Basel, St. Johanns-Ring 19, 4056 Basel, Switzerland
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Publikationsverlauf

Received 19 February 2003
Publikationsdatum:
17. April 2003 (online)

Abstract

Heterocyclic phosphino oxazolines derived from thiophene and benzo[b]thiophene (HetPHOX) form highly active iridium complexes for the enantioselective hydrogenation of olefins and imines.

    References

  • 1 Helmchen G. Pfaltz A. Acc. Chem. Res.  2000,  33:  336 
  • 2a Schnider P. Koch G. Prétôt R. Wang G. Bohnen FM. Krüger C. Pfaltz A. Chem.-Eur. J.  1997,  3:  887 
  • 2b Lightfoot A. Schnider P. Pfaltz A. Angew. Chem. Int. Ed.  1998,  37:  2897 
  • 2c Blackmond DG. Lightfoot A. Pfaltz A. Rosner T. Schnider P. Zimmermann N. Chirality  2000,  12:  442 
  • 3 Cozzi PG. Zimmermann N. Hilgraf R. Schaffner S. Pfaltz A. Adv. Synth. Catal.  2001,  343:  450 
  • 4a Blankenstein J. Pfaltz A. Angew. Chem. Int. Ed.  2001,  40:  4445 
  • 4b Menges F. Pfaltz A. Adv. Synth. Catal.  2002,  344:  40 
  • 5a Review: Pfaltz A. Blankenstein J. Hilgraf R. Hörmann E. McIntyre S. Menges F. Schönleber M. Smidt SP. Wüstenberg B. Zimmermann N. Adv. Synth. Catal.  2003,  345:  33 
  • 5b Hou D.-R. Reibenspies J. Colacot TJ. Burgess K. Chem.-Eur. J.  2001,  7:  5391 
  • 5c Chiral phospholane-oxazoline ligands: Tang W. Wang W. Zhang X. Angew. Chem. Int. Ed.  2003,  42:  943 
  • 5d Hydrogenation with chiral imidazolylidines: Powell MT. Hou D.-R. Perry MC. Cui X. Burgess K. J. Am. Chem. Soc.  2001,  123:  8878 
  • 6 End N, Berens U, Stoessel C, and Cozzi PG. inventors; (CibaSC AG), Patent Application,  PCT/EP02/08588. 
  • 7a Tietze LF. Lohmann JK. Synlett  2002,  2083 
  • 7b Review on allylic substitution reactions: Pfaltz A. Lautens M. In Comprehensive Asymmetric Catalysis   Vol. II:  Jacobsen EJ. Pfaltz A. Yamamoto H. Springer; Berlin: 1999.  Chap. 24. p.833-844  
  • 10a Menges F. Neuburger M. Pfaltz A. Org. Lett.  2002,  4:  4713 
  • 10b Busacca C. inventors; Patent Application, WO  01/18012.  (Boehringer Ingelheim Pharmaceuticals)
8

Single crystals of complex 6c were obtained by layering a chloroform solution with pentane. Crystallographic data have been deposited under CCDC 203958.

9

Smidt, S. P.; Mukherjee, P.; Pfaltz, A.; Neuburger, M., unpublished results.