An enantioselective approach to the preparation of chiral sulfones by ir-catalyzed asymmetric hydrogenation

Journal of the American Chemical Society

Volumn 136, Issue 47, 2014, Pages 16557-16562

  Peters, Byron K ^a   Zhou, Taigang ^a   Rujirawanich, Janjira ^b   Cadu, Alban ^b   Singh, Thishana ^a,b   Rabten, Wangchuk ^a   Kerdphon, Sutthichat ^a   Andersson, Pher G ^a  

^a STOCKHOLM UNIVERSITY   (Sweden)

^b UPPSALA UNIVERSITY   (Sweden)

Author keywords

[No Author keywords available]

Indexed keywords

CATALYSIS; ENANTIOSELECTIVITY; IRIDIUM COMPOUNDS; ISOMERS;

ASYMMETRIC HYDROGENATION; E-ISOMERS; ENANTIOSELECTIVE APPROACH; HIGH ENANTIOSELECTIVITY; HOMOALLYLIC SULFONES;

HYDROGENATION;

ALKENE; ALKYL GROUP; ALLYL COMPOUND; IRIDIUM; SULFONE DERIVATIVE; VINYL DERIVATIVE;

ARTICLE; ASYMMETRIC CATALYSIS; CATALYST; CHEMICAL BOND; CHEMICAL STRUCTURE; CHIRALITY; DIASTEREOISOMER; ENANTIOMER; ENANTIOSELECTIVITY; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HYDROGENATION; ISOMER; PROTON NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY; SYNTHESIS;

EID: 84914166279     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja5079877     Document Type: Article

References (60)

1. Blakemore, P. R. J. Chem. Soc., Perkin Trans. 1 2002, 2563-2585
2. Taylor, R. J. K.; Casy, G. Org. React. (N.Y., Engl. Transl.) 2003, 62, 357-475
3. Carretero, J. C.; Arrayás, R. G.; Adrio, J. In Organosulfur Chemistry in Asymmetric Synthesis; Wiley-VCH Verlag GmbH & Co. KGaA: Weinheim, Germany, 2009; pp 291-320.
4. Doswald, S.; Estermann, H.; Kupfer, E.; Stadler, H.; Walther, W.; Weisbrod, T.; Wirz, B.; Wostl, W. Bioorg. Med. Chem. 1994, 2, 403-410
5. Grigg, R. Tetrahedron: Asymmetry 1995, 6, 2475-2486
6. Llamas, T.; Arrayas, R. G.; Carretero, J. C. Org. Lett. 2006, 8, 1795-1798
7. Shimizu, I.; Ohashi, Y.; Tsuji, J. Tetrahedron Lett. 1984, 25, 5183-5186
8. Kennedy, M.; McKervey, M. A.; Maguire, A. R.; Roos, G. H. P. J. Chem. Soc., Chem. Commun. 1990, 361-362
9. Honma, M.; Sawada, T.; Fujisawa, Y.; Utsugi, M.; Watanabe, H.; Umino, A.; Matsumura, T.; Hagihara, T.; Takano, M.; Nakada, M. J. Am. Chem. Soc. 2003, 125, 2860-2861
10. Honma, M.; Nakada, M. Tetrahedron Lett. 2003, 44, 9007-9011
11. Sawada, T.; Nakada, M. Adv. Synth. Catal. 2005, 347, 1527-1532
12. Takeda, H.; Watanabe, H.; Nakada, M. Tetrahedron 2006, 62, 8054-8063
13. Takano, M.; Umino, A.; Nakada, M. Org. Lett. 2004, 6, 4897-4900
14. Mauleon, P.; Carretero, J. C. Org. Lett. 2004, 6, 3195-3198
15. Mauleon, P.; Alonso, I.; Rodriguez, R. M.; Carretero, J. C. J. Org. Chem. 2007, 72, 9924-9935
16. Mauleon, P.; Carretero, J. C. Chem. Commun. 2005, 4961-4963
17. Mosse, S.; Alexakis, A. Org. Lett. 2005, 7, 4361-4364
18. Mossé, S.; Laars, M.; Kriis, K.; Kanger, T.; Alexakis, A. Org. Lett. 2006, 8, 2559-2562
19. Li, H. M.; Song, J.; Liu, X. F.; Deng, L. J. Am. Chem. Soc. 2005, 127, 8948-8949
20. Liu, T. Y.; Long, J.; Li, B. J.; Jiang, L.; Li, R.; Wu, Y.; Ding, L. S.; Chen, Y. C. Org. Biomol. Chem. 2006, 4, 2097-2099
21. Watanabe, Y.; Mase, N.; Furue, R.; Toru, T. Tetrahedron Lett. 2001, 42, 2981-2984
22. Sugimoto, H.; Nakamura, S.; Watanabe, Y.; Toru, T. Tetrahedron: Asymmetry 2003, 14, 3043-3055
23. Jacobsen, E. N.; Pfaltz, A.; Yamamoto, H. Comprehensive Asymmetric Catalysis: I-III; Springer: Berlin, 1999.
24. Ojima, I. Catalytic Asymmetric Synthesis; 3 rd ed.; John Wiley & Sons Inc.: Hoboken, NJ, 2010.
25. Roseblade, S. J.; Pfaltz, A. Acc. Chem. Res. 2007, 40, 1402-1411
26. Woodmansee, D. H.; Pfaltz, A. Top. Organomet. Chem. 2011, 34, 31-76
27. Cadu, A.; Andersson, P. G. J. Organomet. Chem. 2012, 714, 3-11
28. Etayo, P.; Vidal-Ferran, A. Chem. Soc. Rev. 2013, 42, 728-754
29. Cadu, A.; Andersson, P. G. Dalton Trans. 2013, 42, 14345-14356
30. Trifonova, A.; Diesen, J. S.; Chapman, C. J.; Andersson, P. G. Org. Lett. 2004, 6, 3825-3827
31. Kallstrom, K.; Munslow, I. J.; Hedberg, C.; Andersson, P. G. Adv. Synth. Catal. 2006, 348, 2575-2578
32. Cheruku, P.; Gohil, S.; Andersson, P. G. Org. Lett. 2007, 9, 1659-1661
33. Engman, M.; Diesen, J. S.; Paptchikhine, A.; Andersson, P. G. J. Am. Chem. Soc. 2007, 129, 4536-4537
34. Cheruku, P.; Church, T. L.; Trifonova, A.; Wartmann, T.; Andersson, P. G. Tetrahedron Lett. 2008, 49, 7290-7293
35. Cheruku, P.; Paptchikhine, A.; Church, T. L.; Andersson, P. G. J. Am. Chem. Soc. 2009, 131, 8285-8289
36. Engman, M.; Cheruku, P.; Tolstoy, P.; Bergquist, J.; Volker, S. F.; Andersson, P. G. Adv. Synth. Catal. 2009, 351, 375-378
37. Paptchikhine, A.; Cheruku, P.; Engman, M.; Andersson, P. G. Chem. Commun. 2009, 5996-5998
38. Verendel, J. J.; Zhou, T. G.; Li, J. Q.; Paptchikhine, A.; Lebedev, O.; Andersson, P. G. J. Am. Chem. Soc. 2010, 132, 8880
39. Lightfoot, A.; Schnider, P.; Pfaltz, A. Angew. Chem., Int. Ed. 1998, 37, 2897-2899
40. Cadu, A.; Paptchikhine, A.; Andersson, P. G. Synthesis 2011, 2011, 3796-3800
41. Cadu, A.; Upadhyay, P. K.; Andersson, P. G. Asian J. Chem. 2013, 2, 1061-1065
42. Bernasconi, M.; Ramella, V.; Tosatti, P.; Pfaltz, A. Chem. - Eur. J. 2014, 20, 2440-2444
43. Dieguez, M.; Mazuela, J.; Pamies, O.; Verendel, J. J.; Andersson, P. G. J. Am. Chem. Soc. 2008, 130, 7208-7209
44. Kaukoranta, P.; Engman, M.; Hedberg, C.; Bergquist, J.; Andersson, P. G. Adv. Synth. Catal. 2008, 350, 1168-1176
45. Brandt, P.; Hedberg, C.; Andersson, P. G. Chem. - Eur. J. 2003, 9, 339-347
46. Church, T. L.; Rasmussen, T.; Andersson, P. G. Organometallics 2010, 29, 6769-6781
47. Fan, Y.; Cui, X.; Burgess, K.; Hall, M. B. J. Am. Chem. Soc. 2004, 126, 16688-16689
48. Gruber, S.; Pfaltz, A. Angew. Chem., Int. Ed. 2014, 53, 1896-1900
49. Mazuela, J.; Norrby, P.-O.; Andersson, P. G.; Pamies, O.; Diéguez, M. J. Am. Chem. Soc. 2011, 133, 13634-13645
50. Bertus, P.; Phansavath, P.; Ratovelomanana-Vidal, V.; Genet, J. P.; Touati, A. R.; Homri, T.; Ben Hassine, B. Tetrahedron Lett. 1999, 40, 3175-3178
51. Genêt, J. P.; Pinel, C.; Ratovelomanana-Vidal, V.; Mallart, S.; Pfister, X.; Bischoff, L.; De Andrade, M. C. C.; Darses, S.; Galopin, C.; Laffitte, J. A. Tetrahedron: Asymmetry 1994, 5, 675-690
52. Genêt, J. P.; Pinel, C.; Ratovelomanana-Vidal, V.; Mallart, S.; Pfister, X.; De Andrade, M. C. C.; Laffitte, J. A. Tetrahedron: Asymmetry 1994, 5, 665-674
53. Zhang, H. L.; Hou, X. L.; Dai, L. X.; Luo, Z. B. Tetrahedron: Asymmetry 2007, 18, 224-228
54. Misun, M.; Pfaltz, A. Helv. Chim. Acta 1996, 79, 961-972
55. Llamas, T.; Arrayás, R. G.; Carretero, J. C. Angew. Chem., Int. Ed. 2007, 46, 3329-3332
56. Hou, G.-H.; Xie, J.-H.; Yan, P.-C.; Zhou, Q.-L. J. Am. Chem. Soc. 2009, 131, 1366-1367
57. Hou, G.; Li, W.; Ma, M.; Zhang, X.; Zhang, X. J. Am. Chem. Soc. 2010, 132, 12844-12846
58. Zhou, T.; Peters, B.; Maldonado, M. F.; Govender, T.; Andersson, P. G. J. Am. Chem. Soc. 2012, 134, 13592-13595
59. Crabtree, R. Acc. Chem. Res. 1979, 12, 331-337
60. Li, J. Q.; Paptchikhine, A.; Govender, T.; Andersson, P. G. Tetrahedron: Asymmetry 2010, 21, 1328-1333