Diastereo- and enantioselective Pd(II)-catalyzed additions of 2-alkylazaarenes to N -boc imines and nitroalkenes

Journal of the American Chemical Society

Volumn 134, Issue 44, 2012, Pages 18193-18196

  Best, Daniel ^a   Kujawa, Szymon ^a   Lam, Hon Wai ^a  

^a UNIVERSITY OF EDINBURGH   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

ALDIMINES; DEPROTECTION; ENANTIOSELECTIVE; ENANTIOSELECTIVE ADDITION; HIGH YIELD; NITROALKENES; OXAZOLINES;

ENANTIOSELECTIVITY; NITROGEN COMPOUNDS;

PALLADIUM COMPOUNDS;

ALKENE DERIVATIVE; AMINE; IMINE; LEAD; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE;

ADDITION REACTION; ARTICLE; CATALYSIS; CHIRALITY; CONJUGATION; DEPROTECTION REACTION; DIASTEREOISOMER; ENANTIOSELECTIVITY; STEREOCHEMISTRY;

ALKENES; AZA COMPOUNDS; CATALYSIS; HYDROCARBONS, AROMATIC; IMINES; NITRO COMPOUNDS; OXAZOLES; PALLADIUM; STEREOISOMERISM;

EID: 84868579593     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja3083494     Document Type: Article

References (30)

1. Poulsen, T. B.; Jørgensen, K. A. Chem. Rev. 2008, 108, 2903
2. Bandini, M.; Eichholzer, A. Angew. Chem., Int. Ed. 2009, 48, 9608
3. You, S.-L.; Cai, Q.; Zeng, M. Chem. Soc. Rev. 2009, 38, 2190
4. Bartoli, G.; Bencivenni, G.; Dalpozzo, R. Chem. Soc. Rev. 2010, 39, 4449
5. Terrasson, V.; de Figueiredo, R. M.; Campagne, J. M. Eur. J. Org. Chem. 2010, 2635
6. Kobayashi, S.; Mori, Y.; Fossey, J. S.; Salter, M. M. Chem. Rev. 2011, 111, 2626
7. Review of 1-azaallylic anions in heterocyclic chemistry: Mangelinckx, S.; Giubellina, N.; De Kimpe, N. Chem. Rev. 2004, 104, 2353
8. Xu, J.; Wei, L.; Mathvink, R. J.; Edmondson, S. D.; Eiermann, G. J.; He, H.; Leone, J. F.; Leiting, B.; Lyons, K. A.; Marsilio, F.; Patel, R. A.; Patel, S. B.; Petrov, A.; Scapin, G.; Wu, J. K.; Thornberry, N. A.; Weber, A. E. Bioorg. Med. Chem. Lett. 2006, 16, 5373
9. Kolczewski, S.; Marty, H.-P.; Narquizian, R.; Pinard, E.; Stalder, H. U.S. Pat. Appl. 20100210592 A1, 2010.
10. Hamana, H.; Sugasawa, T. Chem. Lett. 1983, 333
11. Hamana, H.; Sugasawa, T. Chem. Lett. 1984, 1591
12. Racemic Rh-catalyzed hydrogenative coupling of vinylazines with N -sulfonylaldimines: Komanduri, V.; Grant, C. D.; Krische, M. J. J. Am. Chem. Soc. 2008, 130, 12592
13. Enantioselective Cu-catalyzed reductive coupling of alkenylazaarenes with ketones: Saxena, A.; Choi, B.; Lam, H. W. J. Am. Chem. Soc. 2012, 134, 8428
14. Trost, B. M.; Thaisrivongs, D. A. J. Am. Chem. Soc. 2008, 130, 14092
15. Trost, B. M.; Thaisrivongs, D. A. J. Am. Chem. Soc. 2009, 131, 12056
16. Trost, B. M.; Thaisrivongs, D. A.; Hartwig, J. J. Am. Chem. Soc. 2011, 133, 12439
17. Fallan, C.; Lam, H. W. Chem.-Eur. J. 2012, 18, 11214
18. Qian, B.; Guo, S.; Shao, J.; Zhu, Q.; Yang, L.; Xia, C.; Huang, H. J. Am. Chem. Soc. 2010, 132, 3650
19. Qian, B.; Guo, S.; Xia, C.; Huang, H. Adv. Synth. Catal. 2010, 352, 3195
20. Qian, B.; Xie, P.; Xie, Y.; Huang, H. Org. Lett. 2011, 13, 2580
21. Rueping, M.; Tolstoluzhsky, N. Org. Lett. 2011, 13, 1095
22. Komai, H.; Yoshino, T.; Matsunaga, S.; Kanai, M. Synthesis 2012, 2185
23. A catalyst-free addition of alkylazaarenes to imines was also recently described: Yan, Y.; Xu, K.; Fang, Y.; Wang, Z. J. Org. Chem. 2011, 76, 6849
24. Komai, H.; Yoshino, T.; Matsunaga, S.; Kanai, M. Org. Lett. 2011, 13, 1706
25. Qian, B.; Shi, D.; Yang, L.; Huang, H. Adv. Synth. Catal. 2012, 2146
26. Amine-catalyzed racemic addition of 3,5-diethyl-4-nitroisoxazole to carbonyl compounds: Adamo, M. F. A.; Suresh, S. Tetrahedron 2009, 65, 990
27. Desimoni, G.; Faita, G.; Mella, M. Tetrahedron 1996, 52, 13649
28. Barrett, A. G. M.; Graboski, G. G. Chem. Rev. 1986, 86, 751
29. Barrett, A. G. M. Chem. Soc. Rev. 1991, 20, 95
30. Berner, O. M.; Tedeschi, L.; Enders, D. Eur. J. Org. Chem. 2002, 1877