Synthesis of sulfoximine-derived P,N ligands and their applications in asymmetric quinoline hydrogenations

Advanced Synthesis and Catalysis

Volumn 350, Issue 7-8, 2008, Pages 1101-1105

  Lu, Sheng Mei ^a   Bolm, Carsten ^a  

^a RWTH AACHEN UNIVERSITY   (Germany)

Author keywords

Asymmetric catalysis; Enantioselectivity; Hydrogenation; Iridium; Quinolines; Sulfoximines

Indexed keywords

EID: 53849143611     PISSN: 16154150     EISSN: 15213897     Source Type: Journal    
DOI: 10.1002/adsc.200800068     Document Type: Article

References (26)

1. For reviews, see: a) P. J. Guiry, C. P. Saunders, Adv. Synth. Catal. 2004, 346, 497;
2. b) S. J. Roseblade, A. Pfaltz, Acc. Chem. Res. 2007, 40, 1402, and references cited therein;
3. c) For a recent example, see: M. N. Cheemala, P. Knochel, Org. Lett. 2007, 9, 3089.
4. For an excellent overview, see: G. Helmchen, A. Pfaltz, Acc. Chem. Res. 2000, 33, 336.
5. For reviews on sulfoximines and their use as chiral ligands in metal catalysis, see: a) M. Harmata, Chemtracts 2003, 16, 660;
6. b) H. Okamura, C. Bolm, Chem. Lett. 2004, 32, 482;
7. c) for a personal account, see: C. Bolm, in: Asymmetric Synthesis with Chemical and Biological Methods, (Eds.: D. Enders, K.-E. Jaeger), Wiley-VCH, Weinheim, 2007, p 149.
8. J. Sedelmeier, C. Bolm, J. Org. Chem. 2007, 72, 8859, and references cited therein.
9. C. Moessner, C. Bolm, Angew. Chem. 2005, 117, 7736;
10. Angew. Chem. Int. Ed. 2005, 44, 7564.
11. For the first synthesis of a naphthalene-bridged P,N-type sulfoximine (compound 9a) and initial studies of iridium-catalyzed imine hydrogenations and palladium-catalyzed allylic alkylations, see: P. Rémy, Dissertation, RWTH Aachen University, 2006.
12. G. Y. Cho, P. Remy, J. Jansson, C. Moessner, C. Bolm, Org. Lett. 2004, 6, 3293.
13. H. O. House, D. G. Koepsell, W. J. Campbell, J. Org. Chem. 1972, 37, 1003.
14. J. Sedelmeier, C. Bolm, J. Org. Chem. 2005, 70, 6904.
15. S. Kainz, A. Brinkmann, W. Leitner, A. Pfaltz, J. Am. Chem. Soc. 1999, 121, 6421.
16. S.-F. Zhu, J.-B. Xie, Y.-Z. Zhang, S. Li, Q.-L. Zhou, J. Am. Chem. Soc. 2006, 128, 12886.
17. For a review, see: Y.-G. Zhou, Acc. Chem. Res. 2007, 40, 1357, and references cited therein.
18. For reviews see: a) P. M. Maitlis, A. Haynes, B. R. James, M. Catellani, G. P. Chiusoli, Dalton Trans. 2004, 3409;
19. b) K. Fagnou, M. Lautens, Angew. Chem. 2002, 114, 26;
20. Angew. Chem. Int. Ed. 2002, 41, 26;
21. c) E. M. Vogl, H. Groeger, M. Shibasaki, Angew. Chem. 1999, 111, 1672;
22. Angew. Chem. Int. Ed. 1999, 38, 1570;
23. d) D. J. Berrisford, C. Bolm, K. B. Sharpless, Angew. Chem. 1995, 107, 1159;
24. Angew. Chem. Int. Ed. Engl. 1995, 34, 1059.
25. a) W. B. Wang, S. M. Lu, P. Y. Yang, X. W. Han, Y. G. Zhou, J. Am. Chem. Soc. 2003, 125, 10536;
26. b) J. E. Shaw, P. R. Stapp, J. Heterocycl. Chem. 1987, 24, 1477.