Nickel-catalyzed enantioselective negishi cross-couplings of racemic secondary α-bromo amides with alkylzinc reagents: (S)-N-benzyl-7-cyano-2- ethyl-N-phenylheptanamide : [Heptanamide, 7-cyano-2-ethyl-N-phenyl-N- (phenylmethyl)-,(2S)-]

Organic Syntheses

Volumn 87, Issue , 2010, Pages 330-338

  Lou, Sha ^c   Fu, Gregory C ^a   Bryan, Christopher S ^b   Lautens, Mark ^c  

^a MASSACHUSETTS INSTITUTE OF TECHNOLOGY   (United States)

^b UNIVERSITY OF TORONTO   (Canada)

^c NONE

Author keywords

[No Author keywords available]

Indexed keywords

EID: 79952559843     PISSN: 00786209     EISSN: 16000730     Source Type: Book Series    
DOI: 10.15227/orgsyn.087.0330     Document Type: Article

References (20)

1. Fischer, C.; Fu, G. C. J. Am. Chem. Soc. 2005, 127, 4594-4595.
2. For leading references, see: (a) Rudolph, A.; Lautens, M. Angew. Chem. Int. Ed. 2009, 48, 2656-2670.
3. (b) Frisch, A. C.; Beller, M. Angew. Chem. Int. Ed. 2005, 44, 674-688.
4. (c) Netherton, M. R.; Fu, G. C. In Topics in Organometallic Chemistry: Palladium in Organic Synthesis; Tsuji, J., Ed.; Springer: New York, 2005; pp 85-108.
5. (d) Netherton, M. R.; Fu, G. C. Adv. Synth. Catal. 2004, 346, 1525-1532.
6. For some examples of other types of metal-catalyzed enantioselective cross-coupling processes, see: (a) Hayashi, T. In Comprehensive Asymmetric Catalysis; Jacobsen, E. N., Pfaltz, A., Yamamoto, H., Eds.; Springer: New York, 1999; Chapter 25.
7. (b) Yin, J.; Buchwald, S. L. J. Am. Chem. Soc. 2000, 122, 12051-12052.
8. (c) Shimada, T.; Cho, Y.-H.; Hayashi, T. J. Am. Chem. Soc. 2002, 124, 13396-13397.
9. (d) Hamada, T.; Chieffi, A.; Åhman, J.; Buchwald, S. L. J. Am. Chem. Soc. 2002, 124, 1261-1268.
10. (e) Willis, M. C.; Powell, L. H. W.; Claverie, C. K.; Watson, S. J. Angew. Chem. Int. Ed. 2004, 43, 1249-1251.
11. Zhou, J.; Fu, G. C. J. Am. Chem. Soc. 2003, 125, 14726-14727.
12. (a) α-bromo amides (Negishi): Fischer, C.; Fu, G. C. J. Am. Chem. Soc. 2005, 127, 4594-4595.
13. (b) haloindanes (Negishi): Arp, F. O.; Fu, G. C. J. Am. Chem. Soc. 2005, 127, 10482-10483.
14. (c) allylic chlorides (Negishi): Son, S.; Fu, G. C. J. Am. Chem. Soc. 2008, 130, 2756-2757.
15. (d) α-bromo esters (Hiyama): Dai, X.; Strotman, N. A.; Fu, G. C. J. Am. Chem. Soc. 2008, 130, 3302-3303.
16. (e) homobenzylic bromides (Suzuki): Saito, B.; Fu, G. C. J. Am. Chem. Soc. 2008, 130, 6694-6695.
17. (f) propargylic halides (Negishi): Smith, S. W.; Fu, G. C. J. Am. Chem. Soc. 2008, 130, 12645-12647.
18. (g) α-bromo ketones (Negishi): Lundin, P. M.; Esquivias, J.; Fu, G. C. Angew. Chem. Int. Ed. 2009, 48, 154-156.
19. For the work of others, see: Caeiro, J.; Sestelo, J. P.; Sarandeses, L. A. Chem. Eur. J. 2008, 14, 741-746.
20. Huo, S. Org. Lett. 2003, 5, 423-425. Preliminary efforts to employ commercially alkylzinc halides (Aldrich) were not successful.