Design, synthesis, and characterization of a new class of amino acid-based chiral borate counteranions

Organometallics

Volumn 23, Issue 12, 2004, Pages 2838-2840

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

^a MCGILL UNIVERSITY   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

ACETONITRILE; ASSOCIATION REACTIONS; BORATE MINERALS; CATALYSIS; CATALYSTS; CONDENSATION; ION EXCHANGE; MATHEMATICAL MODELS; STYRENE; SYNTHESIS (CHEMICAL); TRANSITION METALS; X RAY ANALYSIS;

CYCLOPROPANATION; NONBONDING INTERACTIONS; REACTION PRODUCTS;

AMINO ACIDS;

EID: 2942748313     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om040017g     Document Type: Article

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22. For a review of chiral counteranions, see: (a) Lecour, J.; Hebbe-Viton, V. Chem. Soc. Rev. 2003, 32, 373. For representative examples of chiral counteranions: (b) Boeseken, J.; Mijs, J. A. Recl. Trav. Chim. Pays-Bos 1925, 44, 758. (c) Lacour, J.; Jodry, J. J.; Ginglinger, C.; Torche-Haldimann, S. Angew. Chem., Int. Ed. 1998, 37, 2379. (d) Lacour, J.; Gougon-Ginglinger, C.; Torche-Haldimann, S.; Jordy, J. J. Angew. Chem., Int. Ed. 2000, 39, 3695. (e) Monchaud, D.; Jodry, J. J.; Pomeranc, D.; Heitz, V.; Chambron, J.-C.; Sauvage, J.-P.; Lacour, J. Angew. Chem., Int. Ed. 2002, 41, 2317. (f) Desvergnew-Breuil, V.; Hebbe, V.; Dietrich-Buchecker, C.; Sauvage, J.-P.; Lacour, J. Inorg. Chem. 2003, 42, 255. (g) Green, S.; Nelson, A.; Warriner, S.; Whittaker, B. J. Chem. Soc., Perkin Trans. 1 2000, 4403. (h) Carter, C.; Fletcher, S.; Nelson, A. Tetrahedron, Asymmetry 2003, 14, 1995. (i) Ishihara, K.; Miyata, M.; Hattori, K.; Tada, T.; Yamamoto, H. J. Am. Chem. Soc. 1994, 116, 10520. (j) Ishihara, K.; Kurihara, H.; Matsumoto, M.; Yamamoto, H. J. Am. Chem. Soc. 1998, 120, 6920. (k) Graf, E.; Graff, R.; Hosseini, M. W.; Huguenard, C.; Taulelle, F. Chem. Commun. 1997, 1459. (l) Owen, D. J.; VanDerveer, D.; Schuster, G. B. J. Am. Chem. Soc. 1998, 120, 1705.
23. For a review of chiral counteranions, see: (a) Lecour, J.; Hebbe-Viton, V. Chem. Soc. Rev. 2003, 32, 373. For representative examples of chiral counteranions: (b) Boeseken, J.; Mijs, J. A. Recl. Trav. Chim. Pays-Bos 1925, 44, 758. (c) Lacour, J.; Jodry, J. J.; Ginglinger, C.; Torche-Haldimann, S. Angew. Chem., Int. Ed. 1998, 37, 2379. (d) Lacour, J.; Gougon-Ginglinger, C.; Torche-Haldimann, S.; Jordy, J. J. Angew. Chem., Int. Ed. 2000, 39, 3695. (e) Monchaud, D.; Jodry, J. J.; Pomeranc, D.; Heitz, V.; Chambron, J.-C.; Sauvage, J.-P.; Lacour, J. Angew. Chem., Int. Ed. 2002, 41, 2317. (f) Desvergnew-Breuil, V.; Hebbe, V.; Dietrich-Buchecker, C.; Sauvage, J.-P.; Lacour, J. Inorg. Chem. 2003, 42, 255. (g) Green, S.; Nelson, A.; Warriner, S.; Whittaker, B. J. Chem. Soc., Perkin Trans. 1 2000, 4403. (h) Carter, C.; Fletcher, S.; Nelson, A. Tetrahedron, Asymmetry 2003, 14, 1995. (i) Ishihara, K.; Miyata, M.; Hattori, K.; Tada, T.; Yamamoto, H. J. Am. Chem. Soc. 1994, 116, 10520. (j) Ishihara, K.; Kurihara, H.; Matsumoto, M.; Yamamoto, H. J. Am. Chem. Soc. 1998, 120, 6920. (k) Graf, E.; Graff, R.; Hosseini, M. W.; Huguenard, C.; Taulelle, F. Chem. Commun. 1997, 1459. (l) Owen, D. J.; VanDerveer, D.; Schuster, G. B. J. Am. Chem. Soc. 1998, 120, 1705.
24. For a review of chiral counteranions, see: (a) Lecour, J.; Hebbe-Viton, V. Chem. Soc. Rev. 2003, 32, 373. For representative examples of chiral counteranions: (b) Boeseken, J.; Mijs, J. A. Recl. Trav. Chim. Pays-Bos 1925, 44, 758. (c) Lacour, J.; Jodry, J. J.; Ginglinger, C.; Torche-Haldimann, S. Angew. Chem., Int. Ed. 1998, 37, 2379. (d) Lacour, J.; Gougon-Ginglinger, C.; Torche-Haldimann, S.; Jordy, J. J. Angew. Chem., Int. Ed. 2000, 39, 3695. (e) Monchaud, D.; Jodry, J. J.; Pomeranc, D.; Heitz, V.; Chambron, J.-C.; Sauvage, J.-P.; Lacour, J. Angew. Chem., Int. Ed. 2002, 41, 2317. (f) Desvergnew-Breuil, V.; Hebbe, V.; Dietrich-Buchecker, C.; Sauvage, J.-P.; Lacour, J. Inorg. Chem. 2003, 42, 255. (g) Green, S.; Nelson, A.; Warriner, S.; Whittaker, B. J. Chem. Soc., Perkin Trans. 1 2000, 4403. (h) Carter, C.; Fletcher, S.; Nelson, A. Tetrahedron, Asymmetry 2003, 14, 1995. (i) Ishihara, K.; Miyata, M.; Hattori, K.; Tada, T.; Yamamoto, H. J. Am. Chem. Soc. 1994, 116, 10520. (j) Ishihara, K.; Kurihara, H.; Matsumoto, M.; Yamamoto, H. J. Am. Chem. Soc. 1998, 120, 6920. (k) Graf, E.; Graff, R.; Hosseini, M. W.; Huguenard, C.; Taulelle, F. Chem. Commun. 1997, 1459. (l) Owen, D. J.; VanDerveer, D.; Schuster, G. B. J. Am. Chem. Soc. 1998, 120, 1705.
25. For a review of chiral counteranions, see: (a) Lecour, J.; Hebbe-Viton, V. Chem. Soc. Rev. 2003, 32, 373. For representative examples of chiral counteranions: (b) Boeseken, J.; Mijs, J. A. Recl. Trav. Chim. Pays-Bos 1925, 44, 758. (c) Lacour, J.; Jodry, J. J.; Ginglinger, C.; Torche-Haldimann, S. Angew. Chem., Int. Ed. 1998, 37, 2379. (d) Lacour, J.; Gougon-Ginglinger, C.; Torche-Haldimann, S.; Jordy, J. J. Angew. Chem., Int. Ed. 2000, 39, 3695. (e) Monchaud, D.; Jodry, J. J.; Pomeranc, D.; Heitz, V.; Chambron, J.-C.; Sauvage, J.-P.; Lacour, J. Angew. Chem., Int. Ed. 2002, 41, 2317. (f) Desvergnew-Breuil, V.; Hebbe, V.; Dietrich-Buchecker, C.; Sauvage, J.-P.; Lacour, J. Inorg. Chem. 2003, 42, 255. (g) Green, S.; Nelson, A.; Warriner, S.; Whittaker, B. J. Chem. Soc., Perkin Trans. 1 2000, 4403. (h) Carter, C.; Fletcher, S.; Nelson, A. Tetrahedron, Asymmetry 2003, 14, 1995. (i) Ishihara, K.; Miyata, M.; Hattori, K.; Tada, T.; Yamamoto, H. J. Am. Chem. Soc. 1994, 116, 10520. (j) Ishihara, K.; Kurihara, H.; Matsumoto, M.; Yamamoto, H. J. Am. Chem. Soc. 1998, 120, 6920. (k) Graf, E.; Graff, R.; Hosseini, M. W.; Huguenard, C.; Taulelle, F. Chem. Commun. 1997, 1459. (l) Owen, D. J.; VanDerveer, D.; Schuster, G. B. J. Am. Chem. Soc. 1998, 120, 1705.
26. For a review of chiral counteranions, see: (a) Lecour, J.; Hebbe-Viton, V. Chem. Soc. Rev. 2003, 32, 373. For representative examples of chiral counteranions: (b) Boeseken, J.; Mijs, J. A. Recl. Trav. Chim. Pays-Bos 1925, 44, 758. (c) Lacour, J.; Jodry, J. J.; Ginglinger, C.; Torche-Haldimann, S. Angew. Chem., Int. Ed. 1998, 37, 2379. (d) Lacour, J.; Gougon-Ginglinger, C.; Torche-Haldimann, S.; Jordy, J. J. Angew. Chem., Int. Ed. 2000, 39, 3695. (e) Monchaud, D.; Jodry, J. J.; Pomeranc, D.; Heitz, V.; Chambron, J.-C.; Sauvage, J.-P.; Lacour, J. Angew. Chem., Int. Ed. 2002, 41, 2317. (f) Desvergnew-Breuil, V.; Hebbe, V.; Dietrich-Buchecker, C.; Sauvage, J.-P.; Lacour, J. Inorg. Chem. 2003, 42, 255. (g) Green, S.; Nelson, A.; Warriner, S.; Whittaker, B. J. Chem. Soc., Perkin Trans. 1 2000, 4403. (h) Carter, C.; Fletcher, S.; Nelson, A. Tetrahedron, Asymmetry 2003, 14, 1995. (i) Ishihara, K.; Miyata, M.; Hattori, K.; Tada, T.; Yamamoto, H. J. Am. Chem. Soc. 1994, 116, 10520. (j) Ishihara, K.; Kurihara, H.; Matsumoto, M.; Yamamoto, H. J. Am. Chem. Soc. 1998, 120, 6920. (k) Graf, E.; Graff, R.; Hosseini, M. W.; Huguenard, C.; Taulelle, F. Chem. Commun. 1997, 1459. (l) Owen, D. J.; VanDerveer, D.; Schuster, G. B. J. Am. Chem. Soc. 1998, 120, 1705.
27. For a review of chiral counteranions, see: (a) Lecour, J.; Hebbe-Viton, V. Chem. Soc. Rev. 2003, 32, 373. For representative examples of chiral counteranions: (b) Boeseken, J.; Mijs, J. A. Recl. Trav. Chim. Pays-Bos 1925, 44, 758. (c) Lacour, J.; Jodry, J. J.; Ginglinger, C.; Torche-Haldimann, S. Angew. Chem., Int. Ed. 1998, 37, 2379. (d) Lacour, J.; Gougon-Ginglinger, C.; Torche-Haldimann, S.; Jordy, J. J. Angew. Chem., Int. Ed. 2000, 39, 3695. (e) Monchaud, D.; Jodry, J. J.; Pomeranc, D.; Heitz, V.; Chambron, J.-C.; Sauvage, J.-P.; Lacour, J. Angew. Chem., Int. Ed. 2002, 41, 2317. (f) Desvergnew-Breuil, V.; Hebbe, V.; Dietrich-Buchecker, C.; Sauvage, J.-P.; Lacour, J. Inorg. Chem. 2003, 42, 255. (g) Green, S.; Nelson, A.; Warriner, S.; Whittaker, B. J. Chem. Soc., Perkin Trans. 1 2000, 4403. (h) Carter, C.; Fletcher, S.; Nelson, A. Tetrahedron, Asymmetry 2003, 14, 1995. (i) Ishihara, K.; Miyata, M.; Hattori, K.; Tada, T.; Yamamoto, H. J. Am. Chem. Soc. 1994, 116, 10520. (j) Ishihara, K.; Kurihara, H.; Matsumoto, M.; Yamamoto, H. J. Am. Chem. Soc. 1998, 120, 6920. (k) Graf, E.; Graff, R.; Hosseini, M. W.; Huguenard, C.; Taulelle, F. Chem. Commun. 1997, 1459. (l) Owen, D. J.; VanDerveer, D.; Schuster, G. B. J. Am. Chem. Soc. 1998, 120, 1705.
28. For a review of chiral counteranions, see: (a) Lecour, J.; Hebbe-Viton, V. Chem. Soc. Rev. 2003, 32, 373. For representative examples of chiral counteranions: (b) Boeseken, J.; Mijs, J. A. Recl. Trav. Chim. Pays-Bos 1925, 44, 758. (c) Lacour, J.; Jodry, J. J.; Ginglinger, C.; Torche-Haldimann, S. Angew. Chem., Int. Ed. 1998, 37, 2379. (d) Lacour, J.; Gougon-Ginglinger, C.; Torche-Haldimann, S.; Jordy, J. J. Angew. Chem., Int. Ed. 2000, 39, 3695. (e) Monchaud, D.; Jodry, J. J.; Pomeranc, D.; Heitz, V.; Chambron, J.-C.; Sauvage, J.-P.; Lacour, J. Angew. Chem., Int. Ed. 2002, 41, 2317. (f) Desvergnew-Breuil, V.; Hebbe, V.; Dietrich-Buchecker, C.; Sauvage, J.-P.; Lacour, J. Inorg. Chem. 2003, 42, 255. (g) Green, S.; Nelson, A.; Warriner, S.; Whittaker, B. J. Chem. Soc., Perkin Trans. 1 2000, 4403. (h) Carter, C.; Fletcher, S.; Nelson, A. Tetrahedron, Asymmetry 2003, 14, 1995. (i) Ishihara, K.; Miyata, M.; Hattori, K.; Tada, T.; Yamamoto, H. J. Am. Chem. Soc. 1994, 116, 10520. (j) Ishihara, K.; Kurihara, H.; Matsumoto, M.; Yamamoto, H. J. Am. Chem. Soc. 1998, 120, 6920. (k) Graf, E.; Graff, R.; Hosseini, M. W.; Huguenard, C.; Taulelle, F. Chem. Commun. 1997, 1459. (l) Owen, D. J.; VanDerveer, D.; Schuster, G. B. J. Am. Chem. Soc. 1998, 120, 1705.
29. For a review of chiral counteranions, see: (a) Lecour, J.; Hebbe-Viton, V. Chem. Soc. Rev. 2003, 32, 373. For representative examples of chiral counteranions: (b) Boeseken, J.; Mijs, J. A. Recl. Trav. Chim. Pays-Bos 1925, 44, 758. (c) Lacour, J.; Jodry, J. J.; Ginglinger, C.; Torche-Haldimann, S. Angew. Chem., Int. Ed. 1998, 37, 2379. (d) Lacour, J.; Gougon-Ginglinger, C.; Torche-Haldimann, S.; Jordy, J. J. Angew. Chem., Int. Ed. 2000, 39, 3695. (e) Monchaud, D.; Jodry, J. J.; Pomeranc, D.; Heitz, V.; Chambron, J.-C.; Sauvage, J.-P.; Lacour, J. Angew. Chem., Int. Ed. 2002, 41, 2317. (f) Desvergnew-Breuil, V.; Hebbe, V.; Dietrich-Buchecker, C.; Sauvage, J.-P.; Lacour, J. Inorg. Chem. 2003, 42, 255. (g) Green, S.; Nelson, A.; Warriner, S.; Whittaker, B. J. Chem. Soc., Perkin Trans. 1 2000, 4403. (h) Carter, C.; Fletcher, S.; Nelson, A. Tetrahedron, Asymmetry 2003, 14, 1995. (i) Ishihara, K.; Miyata, M.; Hattori, K.; Tada, T.; Yamamoto, H. J. Am. Chem. Soc. 1994, 116, 10520. (j) Ishihara, K.; Kurihara, H.; Matsumoto, M.; Yamamoto, H. J. Am. Chem. Soc. 1998, 120, 6920. (k) Graf, E.; Graff, R.; Hosseini, M. W.; Huguenard, C.; Taulelle, F. Chem. Commun. 1997, 1459. (l) Owen, D. J.; VanDerveer, D.; Schuster, G. B. J. Am. Chem. Soc. 1998, 120, 1705.
30. For a review of chiral counteranions, see: (a) Lecour, J.; Hebbe-Viton, V. Chem. Soc. Rev. 2003, 32, 373. For representative examples of chiral counteranions: (b) Boeseken, J.; Mijs, J. A. Recl. Trav. Chim. Pays-Bos 1925, 44, 758. (c) Lacour, J.; Jodry, J. J.; Ginglinger, C.; Torche-Haldimann, S. Angew. Chem., Int. Ed. 1998, 37, 2379. (d) Lacour, J.; Gougon-Ginglinger, C.; Torche-Haldimann, S.; Jordy, J. J. Angew. Chem., Int. Ed. 2000, 39, 3695. (e) Monchaud, D.; Jodry, J. J.; Pomeranc, D.; Heitz, V.; Chambron, J.-C.; Sauvage, J.-P.; Lacour, J. Angew. Chem., Int. Ed. 2002, 41, 2317. (f) Desvergnew-Breuil, V.; Hebbe, V.; Dietrich-Buchecker, C.; Sauvage, J.-P.; Lacour, J. Inorg. Chem. 2003, 42, 255. (g) Green, S.; Nelson, A.; Warriner, S.; Whittaker, B. J. Chem. Soc., Perkin Trans. 1 2000, 4403. (h) Carter, C.; Fletcher, S.; Nelson, A. Tetrahedron, Asymmetry 2003, 14, 1995. (i) Ishihara, K.; Miyata, M.; Hattori, K.; Tada, T.; Yamamoto, H. J. Am. Chem. Soc. 1994, 116, 10520. (j) Ishihara, K.; Kurihara, H.; Matsumoto, M.; Yamamoto, H. J. Am. Chem. Soc. 1998, 120, 6920. (k) Graf, E.; Graff, R.; Hosseini, M. W.; Huguenard, C.; Taulelle, F. Chem. Commun. 1997, 1459. (l) Owen, D. J.; VanDerveer, D.; Schuster, G. B. J. Am. Chem. Soc. 1998, 120, 1705.
31. For a review of chiral counteranions, see: (a) Lecour, J.; Hebbe-Viton, V. Chem. Soc. Rev. 2003, 32, 373. For representative examples of chiral counteranions: (b) Boeseken, J.; Mijs, J. A. Recl. Trav. Chim. Pays-Bos 1925, 44, 758. (c) Lacour, J.; Jodry, J. J.; Ginglinger, C.; Torche-Haldimann, S. Angew. Chem., Int. Ed. 1998, 37, 2379. (d) Lacour, J.; Gougon-Ginglinger, C.; Torche-Haldimann, S.; Jordy, J. J. Angew. Chem., Int. Ed. 2000, 39, 3695. (e) Monchaud, D.; Jodry, J. J.; Pomeranc, D.; Heitz, V.; Chambron, J.-C.; Sauvage, J.-P.; Lacour, J. Angew. Chem., Int. Ed. 2002, 41, 2317. (f) Desvergnew-Breuil, V.; Hebbe, V.; Dietrich-Buchecker, C.; Sauvage, J.-P.; Lacour, J. Inorg. Chem. 2003, 42, 255. (g) Green, S.; Nelson, A.; Warriner, S.; Whittaker, B. J. Chem. Soc., Perkin Trans. 1 2000, 4403. (h) Carter, C.; Fletcher, S.; Nelson, A. Tetrahedron, Asymmetry 2003, 14, 1995. (i) Ishihara, K.; Miyata, M.; Hattori, K.; Tada, T.; Yamamoto, H. J. Am. Chem. Soc. 1994, 116, 10520. (j) Ishihara, K.; Kurihara, H.; Matsumoto, M.; Yamamoto, H. J. Am. Chem. Soc. 1998, 120, 6920. (k) Graf, E.; Graff, R.; Hosseini, M. W.; Huguenard, C.; Taulelle, F. Chem. Commun. 1997, 1459. (l) Owen, D. J.; VanDerveer, D.; Schuster, G. B. J. Am. Chem. Soc. 1998, 120, 1705.
32. For full characterization of 3, 5-8, see the Supporting Information.
33. Kaufmann, D.; Boese, R. Angew. Chem., Int. Ed. Engl. 1990, 29, 545.
34. Most weakly coordinating anions have been found to show some degree of coordinative interaction with transition metal cations: (a) Strauss, S. H. Chem. Rev. 1993, 93, 927-942. (b) Macchioni, A. J. Inorg. Chem. 2003, 195, and references within.
35. Most weakly coordinating anions have been found to show some degree of coordinative interaction with transition metal cations: (a) Strauss, S. H. Chem. Rev. 1993, 93, 927-942. (b) Macchioni, A. J. Inorg. Chem. 2003, 195, and references within.
36. The copper salt 6 is isolated with two acetonitrile molecules rather than the expected four for a typical cationic copper(I) complex, suggesting there may be some degree of anion coordination in the solid state.
37. (a) Zollinger, H. Diazo Chemistry II; VCH: Weinheim, 1995.
38. (b) Evans, D. A.; Woerpel, K. A.; Hinman, M. M.; Faul, M. M. J. Am. Chem. Soc. 1991, 113, 726.
39. Tchoubar, L. B. Salt Effects in Organic and Organometallic Chemistry, 1st ed.; VCH: Weinheim, 1992.