The use of a chiral borate counteranion as a 1H NMR shift reagent for cationic copper(I) complexes

Canadian Journal of Chemistry

Volumn 81, Issue 11, 2003, Pages 1280-1284

  Llewellyn, David B ^a   Arndtsen, Bruce A ^a  

^a MCGILL UNIVERSITY   (Canada)

Author keywords

Chiral counteranion; Chiral NMR shift reagent; Copper; Ion pairing

Indexed keywords

ADDITION REACTIONS; CATALYSIS; COMPLEXATION; COPPER; NEGATIVE IONS; NUCLEAR MAGNETIC RESONANCE; POSITIVE IONS; SOLUTIONS;

ENANTIOMERS;

BORON COMPOUNDS;

2,2' BIS(DI 4 TOLYLPHOSPHINO) 1,1' BINAPHTHYL; 2,2' ISOPROPYLIDENEBIS(4 PHENYL 2 OXAZOLINE); BIS(1,1' BI 2 NAPHTHOLATO)BORATE; BORIC ACID; COPPER COMPLEX; NAPHTHYL GROUP; OXAZOLINE DERIVATIVE; REAGENT; UNCLASSIFIED DRUG;

ARTICLE; ASYMMETRIC CATALYSIS; CHIRALITY; ENANTIOMER; PROTON NUCLEAR MAGNETIC RESONANCE;

EID: 1642471651     PISSN: 00084042     EISSN: None     Source Type: Journal    
DOI: 10.1139/v03-141     Document Type: Article

References (31)

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19. For examples in copper catalysis, see: (a) D.A. Evans, M.M. Faul, M.T. Bilodeau, B.A. Anderson, and D.M. Barnes. J. Am. Chem. Soc. 115, 5328 (1993); (b) D. Ferraris, T. Dubbing, B. Young, W.J. Drury III, and T. Lectka. J. Org. Chem. 64, 2168 (1999); (c) D.H. Appela, Y. Moritani, R. Shintani, E.M. Ferreira, and S.L. Buchwald. J. Am. Chem. Soc. 121, 9473 (1999); (d) A. Yanagisawa, H. Kageyama, Y. Nakatsuka, K. Asakawa, Y Matsumoto, and H. Yamamoto. Angew. Chem. Int. Ed. 38, 3701 (1999); (e) S. Saaby, X. Fang, N. Gathergood, and K.A. Jorgensen. Angew. Chem. Int. Ed. 39, 4114 (2000); (f) J.S. Johnson and D.A. Evans. Acc. Chem. Res. 33, 325 (2000).
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21. For examples in copper catalysis, see: (a) D.A. Evans, M.M. Faul, M.T. Bilodeau, B.A. Anderson, and D.M. Barnes. J. Am. Chem. Soc. 115, 5328 (1993); (b) D. Ferraris, T. Dubbing, B. Young, W.J. Drury III, and T. Lectka. J. Org. Chem. 64, 2168 (1999); (c) D.H. Appela, Y. Moritani, R. Shintani, E.M. Ferreira, and S.L. Buchwald. J. Am. Chem. Soc. 121, 9473 (1999); (d) A. Yanagisawa, H. Kageyama, Y. Nakatsuka, K. Asakawa, Y Matsumoto, and H. Yamamoto. Angew. Chem. Int. Ed. 38, 3701 (1999); (e) S. Saaby, X. Fang, N. Gathergood, and K.A. Jorgensen. Angew. Chem. Int. Ed. 39, 4114 (2000); (f) J.S. Johnson and D.A. Evans. Acc. Chem. Res. 33, 325 (2000).
22. For examples in copper catalysis, see: (a) D.A. Evans, M.M. Faul, M.T. Bilodeau, B.A. Anderson, and D.M. Barnes. J. Am. Chem. Soc. 115, 5328 (1993); (b) D. Ferraris, T. Dubbing, B. Young, W.J. Drury III, and T. Lectka. J. Org. Chem. 64, 2168 (1999); (c) D.H. Appela, Y. Moritani, R. Shintani, E.M. Ferreira, and S.L. Buchwald. J. Am. Chem. Soc. 121, 9473 (1999); (d) A. Yanagisawa, H. Kageyama, Y. Nakatsuka, K. Asakawa, Y Matsumoto, and H. Yamamoto. Angew. Chem. Int. Ed. 38, 3701 (1999); (e) S. Saaby, X. Fang, N. Gathergood, and K.A. Jorgensen. Angew. Chem. Int. Ed. 39, 4114 (2000); (f) J.S. Johnson and D.A. Evans. Acc. Chem. Res. 33, 325 (2000).
23. For examples in copper catalysis, see: (a) D.A. Evans, M.M. Faul, M.T. Bilodeau, B.A. Anderson, and D.M. Barnes. J. Am. Chem. Soc. 115, 5328 (1993); (b) D. Ferraris, T. Dubbing, B. Young, W.J. Drury III, and T. Lectka. J. Org. Chem. 64, 2168 (1999); (c) D.H. Appela, Y. Moritani, R. Shintani, E.M. Ferreira, and S.L. Buchwald. J. Am. Chem. Soc. 121, 9473 (1999); (d) A. Yanagisawa, H. Kageyama, Y. Nakatsuka, K. Asakawa, Y Matsumoto, and H. Yamamoto. Angew. Chem. Int. Ed. 38, 3701 (1999); (e) S. Saaby, X. Fang, N. Gathergood, and K.A. Jorgensen. Angew. Chem. Int. Ed. 39, 4114 (2000); (f) J.S. Johnson and D.A. Evans. Acc. Chem. Res. 33, 325 (2000).
24. For examples in copper catalysis, see: (a) D.A. Evans, M.M. Faul, M.T. Bilodeau, B.A. Anderson, and D.M. Barnes. J. Am. Chem. Soc. 115, 5328 (1993); (b) D. Ferraris, T. Dubbing, B. Young, W.J. Drury III, and T. Lectka. J. Org. Chem. 64, 2168 (1999); (c) D.H. Appela, Y. Moritani, R. Shintani, E.M. Ferreira, and S.L. Buchwald. J. Am. Chem. Soc. 121, 9473 (1999); (d) A. Yanagisawa, H. Kageyama, Y. Nakatsuka, K. Asakawa, Y Matsumoto, and H. Yamamoto. Angew. Chem. Int. Ed. 38, 3701 (1999); (e) S. Saaby, X. Fang, N. Gathergood, and K.A. Jorgensen. Angew. Chem. Int. Ed. 39, 4114 (2000); (f) J.S. Johnson and D.A. Evans. Acc. Chem. Res. 33, 325 (2000).
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26. For reviews of the use of BINAP derivatives in asymmetric catalysis: (a) I. Ojima (Editor). Catalytic asymmetric synthesis. Wiley, New York. 2000; (b) S. Akutagawa. Appl. Catal. A, 128, 171 (1995); (c) H. Kumobayashi, T. Miura, N. Sayo, T. Saito, and X. Zhang. Synlett 1055 (2001), and refs. therein.
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29. The formation of similar heterochiral bis-ligated metal complexes has been used to explain the chiral amplification observed in several enantioselective transition metal-catalyzed reactions: (a) S. Kanemasa, Y. Oderaotoshi, S. Sakaguchi, H. Yamamoto, J. Tanaka, E. Wada, and D.P. Curran. J. Am. Chem. Soc. 120, 3074 (1998); (b) S. Crosignani, G. Desimoni, G. Faita, S. Filippone, A. Mortoni, P. Righetti, and M. Zemat. Tetrahedron Lett. 40, 7007 (1999); (c) D.A. Evans, M.C. Kozlowski, J.A. Murray, C.S. Burgey, K.R. Campos, B.T. Connell, and R.J. Staples. J. Am. Chem. Soc. 120, 669 (1999).
30. The formation of similar heterochiral bis-ligated metal complexes has been used to explain the chiral amplification observed in several enantioselective transition metal-catalyzed reactions: (a) S. Kanemasa, Y. Oderaotoshi, S. Sakaguchi, H. Yamamoto, J. Tanaka, E. Wada, and D.P. Curran. J. Am. Chem. Soc. 120, 3074 (1998); (b) S. Crosignani, G. Desimoni, G. Faita, S. Filippone, A. Mortoni, P. Righetti, and M. Zemat. Tetrahedron Lett. 40, 7007 (1999); (c) D.A. Evans, M.C. Kozlowski, J.A. Murray, C.S. Burgey, K.R. Campos, B.T. Connell, and R.J. Staples. J. Am. Chem. Soc. 120, 669 (1999).
31. The formation of similar heterochiral bis-ligated metal complexes has been used to explain the chiral amplification observed in several enantioselective transition metal-catalyzed reactions: (a) S. Kanemasa, Y. Oderaotoshi, S. Sakaguchi, H. Yamamoto, J. Tanaka, E. Wada, and D.P. Curran. J. Am. Chem. Soc. 120, 3074 (1998); (b) S. Crosignani, G. Desimoni, G. Faita, S. Filippone, A. Mortoni, P. Righetti, and M. Zemat. Tetrahedron Lett. 40, 7007 (1999); (c) D.A. Evans, M.C. Kozlowski, J.A. Murray, C.S. Burgey, K.R. Campos, B.T. Connell, and R.J. Staples. J. Am. Chem. Soc. 120, 669 (1999).