Practical asymmetric synthesis of a chiral piperazinone derivative

Organic Process Research and Development

Volumn 17, Issue 8, 2013, Pages 1052-1060

  McLaughlin, Mark ^a   Belyk, Kevin ^a   Chen, Cheng Yi ^a   Linghu, Xin ^a   Pan, Jun ^a   Qian, Gang ^a   Reamer, Robert A ^a   Xu, Yingju ^a  

^a MERCK RESEARCH LABORATORIES   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ASYMMETRIC SYNTHESIS; BENZYLIC; CHIRAL PHOSPHINE LIGANDS; EFFICIENT SYNTHESIS; PROCESS DEVELOPMENT; STEREOCENTERS; SULFAMATES;

LIGANDS; PHOSPHORUS COMPOUNDS;

HYDROGENATION;

EID: 84882789825     PISSN: 10836160     EISSN: 1520586X     Source Type: Journal    
DOI: 10.1021/op400150w     Document Type: Article

References (25)

1. Ho, T. W.; Edvinsson, L.; Goadsby, P. J. Nat. Rev. Neurol. 2010, 6, 573
2. Durham, P. L. Headache 2008, 48, 1269
3. Stovner, L. J.; Hagen, K.; Jensen, R.; Katsarava, Z.; Lipton, R. B.; Scher, A. I.; Steiner, T. J.; Zwart, J. A. Cephalalgia 2007, 27, 193
4. For the discovery of MK-3207, see: Bell, I. M.; Gallicchio, S. N.; Wood, M. R.; Quigley, A. G.; Stump, C. A.; Zartman, C. B.; Fay, J. F.; Li, C.-C.; Lynch, J. J.; Moore, E. L.; Mosser, S. M.; Prueksaritanont, T.; Regan, C. P.; Roller, S.; Salvatore, C. A.; Kane, S. A.; Vacca, J. P.; Selnick, H. G. Med. Chem. Lett. 2010, 1, 24-29
5. Williams, A. J.; Chakthong, S.; Gray, D.; Lawrence, R. M.; Gallagher, T. Org. Lett. 2003, 5, 811
6. Bower, J. F.; Rujirawanicha, J.; Gallagher, T. Org. Biomol. Chem. 2010, 8, 1505
7. Chen, Q.-A.; Ye, Z.-S.; Duan, Y.; Zhou, Y.-G. Chem. Soc. Rev. 2013, 42, 497
8. Etayo, P.; Vidal-Ferran, A. Chem. Soc. Rev. 2013, 42, 728
9. For example, asymmetric hydrogenation affording 1,2-diols, see: Ohkuma, T.; Utsumi, N.; Watanabe, M.; Arai, N.; Murata, K. Org. Lett. 2007, 9, 2565
10. Asymmetric Mannich-type reactions affording β -amino-alcohols, see: Matsunaga, S.; Kumagai, N.; Harada, S.; Shibasaki, M. J. Am. Chem. Soc. 2003, 125, 4712
11. Trost, B. M.; Jaratjaroonphong, J.; Reutrakul, V. J. Am. Chem. Soc. 2006, 128, 2778
12. Moriarty, R. M.; Berglund, B. A.; Penmasta, R. Tetrahedron Lett. 1992, 33, 6065
13. Chen, C.; Feng, X.; Zhang, G.; Zhao, Q.; Huang, G. Synthesis 2008, 3205
14. Moriarty, R. M.; Hou, K.-C.; Prakash, I.; Arora, S. K. Org. Synth. 1986, 64, 138
15. Moriarty, R. M.; Prakash, O.; Duncan, M. P. Synthesis 1985, 943
16. Le, J. C.-D.; Pagenkopf, B. L. J. Org. Chem. 2004, 69, 4177
17. Zhu, G.; Casalnuovo, A. L.; Zhang, X. J. Org. Chem. 1998, 63, 8100
18. Wong, F. F.; Chang, P.-W.; Lin, H.-C.; You, B.-J.; Huang, J.-J.; Lin, S.-K. J. Organomet. Chem. 2009, 694, 3452
19. Paizs, C.; Tosa, M.; Majdik, C.; Bódai, V.; Novák, L.; Irimie, F. D.; Poppe, L. J. Chem. Soc., Perkins Trans. 1 2002, 2400
20. Demir, A. S.; Ahyan, P.; Igdir, A. C.; Duygu, A. N. Tetrahedron 2004, 60, 6509
21. Kuhl, N.; Glorious, F. Chem. Commun. 2011, 47, 573
22. McLaughlin, M.; Belyk, K. M.; Qian, G.; Reamer, R. A.; Chen, C. J. Org. Chem. 2012, 77, 5144
23. Wang, Y.-Q.; Yu, C.-B.; Wang, D.-W.; Wang, X.-B.; Zhou, Y.-G. Org. Lett. 2008, 10, 2071
24. Hansen, K. B.; Hsiao, Y.; Xu, F.; Rivera, N.; Clausen, A.; Kubryk, M.; Krska, S.; Rosner, T.; Simmons, B.; Balsells, J.; Ikemoto, N.; Sun, Y.; Spindler, F.; Malan, C.; Grabowski, E. J. J.; Armstrong, J. D. J. Am. Chem. Soc. 2009, 131, 8798
25. Tilstam, U. Org. Process Res. Dev. 2012, 16, 1273