Stereoretentive Deuteration of α-Chiral Amines with D2O

Journal of the American Chemical Society

Volumn 138, Issue 41, 2016, Pages 13489-13492

  Hale, Lillian V A ^a   Szymczak, Nathaniel K ^a  

^a UNIVERSITY OF MICHIGAN   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AMINES; BINDING ENERGY; CARBON;

BINDING AFFINITIES; CHIRAL AMINES; DEUTERIUM INCORPORATIONS; ELECTRON-DEFICIENT; ENANTIOMERIC PURITY; IMINE INTERMEDIATE; LIGAND DISSOCIATION; PRIMARY AMINES;

DEUTERIUM;

AMINE; DEUTERIUM; HYDROGEN; LIGAND; METHYLCYCLOHEXANE; RUTHENIUM;

ARTICLE; BINDING AFFINITY; CATALYST; CHEMICAL REACTION; CHEMICAL STRUCTURE; CHIRALITY; DEHYDROGENATION; ELECTRON; PROTON NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY;

EID: 84992170542     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/jacs.6b07879     Document Type: Article

References (48)

1. Gant, T. G. J. Med. Chem. 2014, 57, 3595 10.1021/jm4007998
2. Tung, R. D. Future Med. Chem. 2016, 8, 491 10.4155/fmc-2016-0032
3. Harbeson, S. L.; Tung, R. D. Annu. Rep. Med. Chem. 2011, 46, 403 10.1016/B978-0-12-386009-5.00003-5
4. Insa, R. ChemMedChem 2013, 8, 336 10.1002/cmdc.201200552
5. Timmins, G. S. Expert Opin. Ther. Pat. 2014, 24, 1067 10.1517/13543776.2014.943184
6. Isin, E. M.; Elmore, C. S.; Nilsson, G. N.; Thompson, R. A.; Weidolf, L. Chem. Res. Toxicol. 2012, 25, 532 10.1021/tx2005212
7. 4. See: Belleau, B.; Burba, J.; Pindell, M.; Reiffenstein, J. Science 1961, 133, 102 10.1126/science.133.3446.102
8. Halford, B. Chem. Eng. News 2016, 94 (27) 32
9. Atzrodt, J.; Derdau, V.; Fey, T.; Zimmermann, J. Angew. Chem., Int. Ed. 2007, 46, 7744 10.1002/anie.200700039
10. Mondovi, B.; Agro, A. F. Adv. Exp. Med. Biol. 1982, 148, 141 10.1007/978-1-4615-9281-5-12
11. Najjar, S. E.; Blake, M. I.; Lu, M. C. J. Labelled Compd. Radiopharm. 1978, 15, 71 10.1002/jlcr.2580150111
12. Najjar, S. E.; Blake, M. I.; Benoit, P. A.; Lu, M. C. J. Med. Chem. 1978, 21, 555 10.1021/jm00204a010
13. Foreman, R. L.; Siegel, F. P.; Mrtek, R. G. J. Pharm. Sci. 1969, 58, 189 10.1002/jps.2600580209
14. Kańska, M.; Pajak, M. J. Radioanal. Nucl. Chem. 2009, 281, 365 10.1007/s10967-009-0012-z
15. Perel, J. M.; Dawson, D. K.; Dayton, P. G.; Goldberg, L. I. J. Med. Chem. 1972, 15, 714 10.1021/jm00277a005
16. Gynther, J. et al. Acta Chem. Scand. 1988, B42, 433 10.3891/acta.chem.scand.42b-0433
17. Neubert, L.; Michalik, D.; Baehn, S.; Imm, S.; Neumann, H.; Atzrodt, J.; Derdau, V.; Holla, W.; Beller, M. J. Am. Chem. Soc. 2012, 134, 12239 10.1021/ja3041338
18. Alexakis, E.; Hickey, M. J.; Jones, J. R.; Kingston, L. P.; Lockley, W. J. S.; Mather, A. N.; Smith, T.; Wilkinson, D. J. Tetrahedron Lett. 2005, 46, 4291 10.1016/j.tetlet.2005.04.095
19. Takahashi, M.; Oshima, K.; Matsubara, S. Chem. Lett. 2005, 34, 192 10.1246/cl.2005.192
20. Dobereiner, G. E.; Crabtree, R. H. Chem. Rev. 2010, 110, 681 10.1021/cr900202j
21. Conley, B. L.; Pennington-Boggio, M. K.; Boz, E.; Williams, T. J. Chem. Rev. 2010, 110, 2294 10.1021/cr9003133
22. Ahn, Y.; Ko, S.-B.; Kim, M.-J.; Park, J. Coord. Chem. Rev. 2008, 252, 647 10.1016/j.ccr.2007.09.009
23. Macgregor, S. A.; Vadivelu, P. Organometallics 2007, 26, 3651 10.1021/om700276p
24. Zhao, J.; Hesslink, H.; Hartwig, J. F. J. Am. Chem. Soc. 2001, 123, 7220 10.1021/ja010417k
25. Warner, M. C.; Bäckvall, J.-E. Acc. Chem. Res. 2013, 46, 2545 10.1021/ar400038g
26. Stark, G. A.; Gladysz, J. A. Inorg. Chem. 1996, 35, 5509 10.1021/ic960302v
27. Bornschein, C.; Gustafson, K. P. J.; Verho, O.; Beller, M.; Bäckvall, J.-E. Chem.-Eur. J. 2016, 22, 11583 10.1002/chem.201601793
28. Taglang, C.; Perato, S.; Sam Lone, A.; Puente, C.; Dugave, C.; Rousseau, B.; Pieters, G.; Martinez-Prieto, L. M.; del Rosal, I.; Maron, L.; Poteau, R.; Chaudret, B.; Philippot, K. Angew. Chem., Int. Ed. 2015, 54, 10474 10.1002/anie.201504554
29. 2 in situ: Bhatia, S.; Spahlinger, G.; Boukhumseen, N.; Boll, Q.; Li, Z.; Jackson, J. E. Eur. J. Org. Chem. 2016, 2016, 4230 10.1002/ejoc.201600719
30. Tseng, K.-N. T.; Kampf, J. W.; Szymczak, N. K. Organometallics 2013, 32, 2046 10.1021/om4000677
31. Tseng, K.-N. T.; Rizzi, A. M.; Szymczak, N. K. J. Am. Chem. Soc. 2013, 135, 16352 10.1021/ja409223a
32. Tseng, K.-N. T.; Szymczak, N. K. Synlett 2014, 25, 2385 10.1055/s-0034-1378543
33. Tseng, K.-N. T.; Kampf, J. W.; Szymczak, N. K. ACS Catal. 2015, 5, 5468 10.1021/acscatal.5b00952
34. Tseng, K.-N. T.; Lin, S.; Kampf, J. W.; Szymczak, N. K. Chem. Commun. (Cambridge, U. K.) 2016, 52, 2901 10.1039/C5CC09913G
35. Hale, L. V. A.; Malakar, T.; Tseng, K.-N. T.; Zimmerman, P. M.; Paul, A.; Szymczak, N. K. ACS Catal. 2016, 6, 4799 10.1021/acscatal.6b01465
36. Nogradi, M. Stereoselective Synthesis: A Practical Approach, 2 nd ed.; VCH: Weinheim, 1995.
37. For a representative example, see: Bizet, V.; Pannecoucke, X.; Renaud, J.-L.; Cahard, D. Angew. Chem., Int. Ed. 2012, 51, 6467 10.1002/anie.201200827
38. Frost, B. J.; Mebi, C. A. Organometallics 2004, 23, 5317 10.1021/om049501+
39. Tseng, K.-N. T.; Kampf, J. W.; Szymczak, N. K. ACS Catal. 2015, 5, 411 10.1021/cs501820w
40. Thalèn, L. K.; Zhao, D.; Sortais, J.; Paetzold, J.; Hoben, C.; Bäckvall, J.-E. Chem.-Eur. J. 2009, 15, 3403 10.1002/chem.200802303
41. Knight, A.; Hemmings, J. L.; Winfield, I.; Leuenberger, M.; Frattini, E.; Frenguelli, B. G.; Dowell, S. J.; Lochner, M.; Ladds, G. J. Med. Chem. 2016, 59, 947 10.1021/acs.jmedchem.5b01402
42. Giardina, G. A. M.; Sarau, H. M.; Farina, C.; Medhurst, A. D.; Grugni, M.; Foley, J. J.; Raveglia, L. F.; Schmidt, D. B.; Rigolio, B.; Vassallo, M.; Vecchietti, V.; Hay, D. W. P. J. Med. Chem. 1996, 39, 2281 10.1021/jm9602423
43. Dunn, P. J.; Hii, K. K.; Krische, M. J.; Williams, M. T., Eds. Sustainable Catalysis: Challenges and Practices for the Pharmaceutical and Fine Chemical Industries; John Wiley & Sons, Inc.: New York, 2013.
44. Collins, K. D.; Glorius, F. Nat. Chem. 2013, 5, 597 10.1038/nchem.1669
45. The binding affinity of α-methylbenzylidenimine is expected to be higher than that of benzaldimine. As an analogy, ketones typically have a higher binding affinity than aldehydes. See: Sanders, J. K. M.; Williams, D. H. J. Am. Chem. Soc. 1971, 93, 641 10.1021/ja00732a015
46. Bernskoetter, W. H.; Brookhart, M. Organometallics 2008, 27, 2036 10.1021/om701148t
47. Wang, Z.; Belli, J.; Jensen, C. M. Faraday Discuss. 2011, 151, 297 10.1039/c1fd00002k
48. Chaudret, B.; Poilblanc, R. Organometallics 1985, 4, 1722 10.1021/om00129a005