Multiple solution species of titanium (IV) 1,1′-Bi-2-naphtholate elucidated by NMR and CD spectroscopy

Organometallics

Volumn 23, Issue 18, 2004, Pages 4223-4229

  Pescitelli, Gennaro ^a   Bari, Lorenzo Di ^a   Salvadori, Piero ^a  

^a UNIVERSITY OF PISA   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

ALKYL GROUPS; COMPLEXES; PRECURSORS; SOLID STATE STRUCTURE;

MIXTURES; MOLECULAR STRUCTURE; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; SOLUTIONS; THERMAL EFFECTS; TITANIUM COMPOUNDS; TITRATION;

ORGANOMETALLICS;

EID: 4444316657     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om049709v     Document Type: Article

References (60)

1. (a) Rosini, C.; Franzini, L.; Raffaelli, A.; Salvadori, P. Synthesis 1992, 503-517.
2. (b) Pu, L. Chem. Rev. 1998, 98, 2405-2494.
3. (c) Chen, Y.; Yekta, S.; Yudin, A. K. Chem. Rev. 2003, 103, 3155-3211.
4. (a) Noyori, R.; Takaya, H. Chem. Scr. 1985, 25, 88-89.
5. (b) Whitesell, J. K. Chem. Rev. 1989, 59, 1581-1590.
6. Boyle, T. J.; Barnes, D. L.; Heppert, J. A.; Morales, L.; Takusagawa, F. Organometallics 1992, 11, 1112-1126.
7. Balsells, J.; Davis, T. J.; Carroll, P.; Walsh, P. J. J. Am. Chem. Soc. 2002, 124, 10336-10348.
8. (a) Mori, M.; Nakai, T. Tetrahedron Lett. 1987, 38, 6233-6236.
9. (b) Zhang, F.-Y.; Yip, C.-W.; Cao, R.; Chan, A. S. C. Tetrahedron: Asymmetry 1997, 8, 585-589.
10. For the most recent examples concerning modified BINOLs see: (a) Nakamura, Y.; Takeuchi, S.; Okumura, K.; Ohgo, Y.; Curran, D. P. Tetrahedron 2002, 58, 3963-3969. (b) Lee, S. J.; Hu, A.; Lin, W. J. Am. Chem. Soc. 2002, 124, 12948-12949. Nakamura, Y.; Takeuchi, S.; Ohgo, Y. J. Fluorine Chem. 2003, 120, 121-129. Harada, T.; Hiraoka, Y.; Kusukawa, T.; Marutani, Y.; Matsui, S.; Nakatsugawa, M.; Kanda, K. Org. Lett. 2008, 5, 5059-5062. (e) Liu, G.-H.; Tang, W.-J.; Fan, Q.-H Tetrahedron 2003, 59, 8603-8611.
11. For the most recent examples concerning modified BINOLs see: (a) Nakamura, Y.; Takeuchi, S.; Okumura, K.; Ohgo, Y.; Curran, D. P. Tetrahedron 2002, 58, 3963-3969. (b) Lee, S. J.; Hu, A.; Lin, W. J. Am. Chem. Soc. 2002, 124, 12948-12949. Nakamura, Y.; Takeuchi, S.; Ohgo, Y. J. Fluorine Chem. 2003, 120, 121-129. Harada, T.; Hiraoka, Y.; Kusukawa, T.; Marutani, Y.; Matsui, S.; Nakatsugawa, M.; Kanda, K. Org. Lett. 2008, 5, 5059-5062. (e) Liu, G.-H.; Tang, W.-J.; Fan, Q.-H Tetrahedron 2003, 59, 8603-8611.
12. For the most recent examples concerning modified BINOLs see: (a) Nakamura, Y.; Takeuchi, S.; Okumura, K.; Ohgo, Y.; Curran, D. P. Tetrahedron 2002, 58, 3963-3969. (b) Lee, S. J.; Hu, A.; Lin, W. J. Am. Chem. Soc. 2002, 124, 12948-12949. Nakamura, Y.; Takeuchi, S.; Ohgo, Y. J. Fluorine Chem. 2003, 120, 121-129. Harada, T.; Hiraoka, Y.; Kusukawa, T.; Marutani, Y.; Matsui, S.; Nakatsugawa, M.; Kanda, K. Org. Lett. 2008, 5, 5059-5062. (e) Liu, G.-H.; Tang, W.-J.; Fan, Q.-H Tetrahedron 2003, 59, 8603-8611.
13. For the most recent examples concerning modified BINOLs see: (a) Nakamura, Y.; Takeuchi, S.; Okumura, K.; Ohgo, Y.; Curran, D. P. Tetrahedron 2002, 58, 3963-3969. (b) Lee, S. J.; Hu, A.; Lin, W. J. Am. Chem. Soc. 2002, 124, 12948-12949. Nakamura, Y.; Takeuchi, S.; Ohgo, Y. J. Fluorine Chem. 2003, 120, 121-129. Harada, T.; Hiraoka, Y.; Kusukawa, T.; Marutani, Y.; Matsui, S.; Nakatsugawa, M.; Kanda, K. Org. Lett. 2008, 5, 5059-5062. (e) Liu, G.-H.; Tang, W.-J.; Fan, Q.-H Tetrahedron 2003, 59, 8603-8611.
14. For the most recent examples concerning modified BINOLs see: (a) Nakamura, Y.; Takeuchi, S.; Okumura, K.; Ohgo, Y.; Curran, D. P. Tetrahedron 2002, 58, 3963-3969. (b) Lee, S. J.; Hu, A.; Lin, W. J. Am. Chem. Soc. 2002, 124, 12948-12949. Nakamura, Y.; Takeuchi, S.; Ohgo, Y. J. Fluorine Chem. 2003, 120, 121-129. Harada, T.; Hiraoka, Y.; Kusukawa, T.; Marutani, Y.; Matsui, S.; Nakatsugawa, M.; Kanda, K. Org. Lett. 2008, 5, 5059-5062. (e) Liu, G.-H.; Tang, W.-J.; Fan, Q.-H Tetrahedron 2003, 59, 8603-8611.
15. Waltz, K. M.; Carroll, P. J.; Walsh, P. J. Organometallics 2004, 23, 127-134.
16. Davis, T. J.; Balsella, J.; Carroll, P. J.; Walsh, P. J. Org. Lett. 2001, 3, 699-702.
17. (a) Bradley, D. C.; Mehrotra, R. C.; Gaur, D. P. Metal Alkoxides; Academic Press: New York, 1978.
18. (b) Wu, Y.-T.; Ho, Y.-C.; Lin, C.-C.; Gau, H.-M. Inorg. Chem. 1898, 35, 5948-5952. See also refs 10a.1.
19. For recent noteworthy examples of structural studies in solution of catalytically active titanium complexes with alkoxy or aryloxy ligands, see: (a) Finn, M. G.; Sharpless, K. B. J. Am. Chem. Soc. 1991, 113, 113-126. (b) Sasaki, C.; Nakajima, K.; Kojima, M.; Junnosuke, F. Bull. Chem. Soc. Jpn. 1991, 64, 1318-1324. Seebach, D.; Plattner, D. A.; Beck, A. K. Wang, Y. M.; Hunziker, D. Helv. Chim. Acta 1992, 75, 2171-2209. Hayashi, M.; Miyamoto, Y.; Inoue, T.; Oguni, N. J. Org. Chem. 1993, 58, 1515-1522. (e) Tonchio, M.; Licini, G.; Modena, G.; Bortolini, G.; Moro, S.; Nugent, W. A. J. Am. Chem. Soc. 1999, 121, 6258-6268. (f) Potvin, P. G.; Fieldhouse, B. G. Tetrahedron: Asymmetry 1999, 10, 1661-1672. (g) You, J.-S.; Shao, M.-Y.; Gau, H.-M. Organometallics 2000, 19, 3368-3373. (h) Flores-Lopéz, L. Z.; Parra-Hake, M.; Somanathan, R.; Walsh, P. J. Organometallics 2000, 19, 2153-2160. Sarvay, I.; Almqvist, F.; Frejd, T. Chem. Eur. J. 2001, 7, 2158-2166. (j) Hintermann, L.; Broggini, D.; Togni, A. Helv. Chim. Acta 2002, 85, 1597-1612. (k) Wu, K.-H.; Gau, H.-M. Organometallics 2003, 22, 5193-5200. Pérez, Y.; del Hierro, I.; Fajardo, M.; Otero, A. J. Organomet. Chem. 2003, 679, 220-228. Wu, K.-H.; Gau, H.-M. Organometallics 2004, 23, 580-588. (n) Ladipo, F. T.; Sarveswaran, V.; Kingston, J. V.; Huyck, R. A.; Bylikin, S. Y.; Carr, S. D.; Watts, R.; Parkin, S. J. Organomet. Chem. 2004, 689, 502-514. (o) Takashima, Y.; Nakayama, Y.; Hirao, T. ; Yasuda, H.; Harada, A. J. Organomet. Chem. 2004, 689, 612-619. (p) Corden, J. P.; Errington, W.; Moore, P.; Partridge, M. G.; Wallbridge, M. G. H. Dalton Trans. 2004, 1846-1851.
20. For recent noteworthy examples of structural studies in solution of catalytically active titanium complexes with alkoxy or aryloxy ligands, see: (a) Finn, M. G.; Sharpless, K. B. J. Am. Chem. Soc. 1991, 113, 113-126. (b) Sasaki, C.; Nakajima, K.; Kojima, M.; Junnosuke, F. Bull. Chem. Soc. Jpn. 1991, 64, 1318-1324. Seebach, D.; Plattner, D. A.; Beck, A. K. Wang, Y. M.; Hunziker, D. Helv. Chim. Acta 1992, 75, 2171-2209. Hayashi, M.; Miyamoto, Y.; Inoue, T.; Oguni, N. J. Org. Chem. 1993, 58, 1515-1522. (e) Tonchio, M.; Licini, G.; Modena, G.; Bortolini, G.; Moro, S.; Nugent, W. A. J. Am. Chem. Soc. 1999, 121, 6258-6268. (f) Potvin, P. G.; Fieldhouse, B. G. Tetrahedron: Asymmetry 1999, 10, 1661-1672. (g) You, J.-S.; Shao, M.-Y.; Gau, H.-M. Organometallics 2000, 19, 3368-3373. (h) Flores-Lopéz, L. Z.; Parra-Hake, M.; Somanathan, R.; Walsh, P. J. Organometallics 2000, 19, 2153-2160. Sarvay, I.; Almqvist, F.; Frejd, T. Chem. Eur. J. 2001, 7, 2158-2166. (j) Hintermann, L.; Broggini, D.; Togni, A. Helv. Chim. Acta 2002, 85, 1597-1612. (k) Wu, K.-H.; Gau, H.-M. Organometallics 2003, 22, 5193-5200. Pérez, Y.; del Hierro, I.; Fajardo, M.; Otero, A. J. Organomet. Chem. 2003, 679, 220-228. Wu, K.-H.; Gau, H.-M. Organometallics 2004, 23, 580-588. (n) Ladipo, F. T.; Sarveswaran, V.; Kingston, J. V.; Huyck, R. A.; Bylikin, S. Y.; Carr, S. D.; Watts, R.; Parkin, S. J. Organomet. Chem. 2004, 689, 502-514. (o) Takashima, Y.; Nakayama, Y.; Hirao, T. ; Yasuda, H.; Harada, A. J. Organomet. Chem. 2004, 689, 612-619. (p) Corden, J. P.; Errington, W.; Moore, P.; Partridge, M. G.; Wallbridge, M. G. H. Dalton Trans. 2004, 1846-1851.
21. For recent noteworthy examples of structural studies in solution of catalytically active titanium complexes with alkoxy or aryloxy ligands, see: (a) Finn, M. G.; Sharpless, K. B. J. Am. Chem. Soc. 1991, 113, 113-126. (b) Sasaki, C.; Nakajima, K.; Kojima, M.; Junnosuke, F. Bull. Chem. Soc. Jpn. 1991, 64, 1318-1324. Seebach, D.; Plattner, D. A.; Beck, A. K. Wang, Y. M.; Hunziker, D. Helv. Chim. Acta 1992, 75, 2171-2209. Hayashi, M.; Miyamoto, Y.; Inoue, T.; Oguni, N. J. Org. Chem. 1993, 58, 1515-1522. (e) Tonchio, M.; Licini, G.; Modena, G.; Bortolini, G.; Moro, S.; Nugent, W. A. J. Am. Chem. Soc. 1999, 121, 6258-6268. (f) Potvin, P. G.; Fieldhouse, B. G. Tetrahedron: Asymmetry 1999, 10, 1661-1672. (g) You, J.-S.; Shao, M.-Y.; Gau, H.-M. Organometallics 2000, 19, 3368-3373. (h) Flores-Lopéz, L. Z.; Parra-Hake, M.; Somanathan, R.; Walsh, P. J. Organometallics 2000, 19, 2153-2160. Sarvay, I.; Almqvist, F.; Frejd, T. Chem. Eur. J. 2001, 7, 2158-2166. (j) Hintermann, L.; Broggini, D.; Togni, A. Helv. Chim. Acta 2002, 85, 1597-1612. (k) Wu, K.-H.; Gau, H.-M. Organometallics 2003, 22, 5193-5200. Pérez, Y.; del Hierro, I.; Fajardo, M.; Otero, A. J. Organomet. Chem. 2003, 679, 220-228. Wu, K.-H.; Gau, H.-M. Organometallics 2004, 23, 580-588. (n) Ladipo, F. T.; Sarveswaran, V.; Kingston, J. V.; Huyck, R. A.; Bylikin, S. Y.; Carr, S. D.; Watts, R.; Parkin, S. J. Organomet. Chem. 2004, 689, 502-514. (o) Takashima, Y.; Nakayama, Y.; Hirao, T. ; Yasuda, H.; Harada, A. J. Organomet. Chem. 2004, 689, 612-619. (p) Corden, J. P.; Errington, W.; Moore, P.; Partridge, M. G.; Wallbridge, M. G. H. Dalton Trans. 2004, 1846-1851.
22. For recent noteworthy examples of structural studies in solution of catalytically active titanium complexes with alkoxy or aryloxy ligands, see: (a) Finn, M. G.; Sharpless, K. B. J. Am. Chem. Soc. 1991, 113, 113-126. (b) Sasaki, C.; Nakajima, K.; Kojima, M.; Junnosuke, F. Bull. Chem. Soc. Jpn. 1991, 64, 1318-1324. Seebach, D.; Plattner, D. A.; Beck, A. K. Wang, Y. M.; Hunziker, D. Helv. Chim. Acta 1992, 75, 2171-2209. Hayashi, M.; Miyamoto, Y.; Inoue, T.; Oguni, N. J. Org. Chem. 1993, 58, 1515-1522. (e) Tonchio, M.; Licini, G.; Modena, G.; Bortolini, G.; Moro, S.; Nugent, W. A. J. Am. Chem. Soc. 1999, 121, 6258-6268. (f) Potvin, P. G.; Fieldhouse, B. G. Tetrahedron: Asymmetry 1999, 10, 1661-1672. (g) You, J.-S.; Shao, M.-Y.; Gau, H.-M. Organometallics 2000, 19, 3368-3373. (h) Flores-Lopéz, L. Z.; Parra-Hake, M.; Somanathan, R.; Walsh, P. J. Organometallics 2000, 19, 2153-2160. Sarvay, I.; Almqvist, F.; Frejd, T. Chem. Eur. J. 2001, 7, 2158-2166. (j) Hintermann, L.; Broggini, D.; Togni, A. Helv. Chim. Acta 2002, 85, 1597-1612. (k) Wu, K.-H.; Gau, H.-M. Organometallics 2003, 22, 5193-5200. Pérez, Y.; del Hierro, I.; Fajardo, M.; Otero, A. J. Organomet. Chem. 2003, 679, 220-228. Wu, K.-H.; Gau, H.-M. Organometallics 2004, 23, 580-588. (n) Ladipo, F. T.; Sarveswaran, V.; Kingston, J. V.; Huyck, R. A.; Bylikin, S. Y.; Carr, S. D.; Watts, R.; Parkin, S. J. Organomet. Chem. 2004, 689, 502-514. (o) Takashima, Y.; Nakayama, Y.; Hirao, T. ; Yasuda, H.; Harada, A. J. Organomet. Chem. 2004, 689, 612-619. (p) Corden, J. P.; Errington, W.; Moore, P.; Partridge, M. G.; Wallbridge, M. G. H. Dalton Trans. 2004, 1846-1851.
23. For recent noteworthy examples of structural studies in solution of catalytically active titanium complexes with alkoxy or aryloxy ligands, see: (a) Finn, M. G.; Sharpless, K. B. J. Am. Chem. Soc. 1991, 113, 113-126. (b) Sasaki, C.; Nakajima, K.; Kojima, M.; Junnosuke, F. Bull. Chem. Soc. Jpn. 1991, 64, 1318-1324. Seebach, D.; Plattner, D. A.; Beck, A. K. Wang, Y. M.; Hunziker, D. Helv. Chim. Acta 1992, 75, 2171-2209. Hayashi, M.; Miyamoto, Y.; Inoue, T.; Oguni, N. J. Org. Chem. 1993, 58, 1515-1522. (e) Tonchio, M.; Licini, G.; Modena, G.; Bortolini, G.; Moro, S.; Nugent, W. A. J. Am. Chem. Soc. 1999, 121, 6258-6268. (f) Potvin, P. G.; Fieldhouse, B. G. Tetrahedron: Asymmetry 1999, 10, 1661-1672. (g) You, J.-S.; Shao, M.-Y.; Gau, H.-M. Organometallics 2000, 19, 3368-3373. (h) Flores-Lopéz, L. Z.; Parra-Hake, M.; Somanathan, R.; Walsh, P. J. Organometallics 2000, 19, 2153-2160. Sarvay, I.; Almqvist, F.; Frejd, T. Chem. Eur. J. 2001, 7, 2158-2166. (j) Hintermann, L.; Broggini, D.; Togni, A. Helv. Chim. Acta 2002, 85, 1597-1612. (k) Wu, K.-H.; Gau, H.-M. Organometallics 2003, 22, 5193-5200. Pérez, Y.; del Hierro, I.; Fajardo, M.; Otero, A. J. Organomet. Chem. 2003, 679, 220-228. Wu, K.-H.; Gau, H.-M. Organometallics 2004, 23, 580-588. (n) Ladipo, F. T.; Sarveswaran, V.; Kingston, J. V.; Huyck, R. A.; Bylikin, S. Y.; Carr, S. D.; Watts, R.; Parkin, S. J. Organomet. Chem. 2004, 689, 502-514. (o) Takashima, Y.; Nakayama, Y.; Hirao, T. ; Yasuda, H.; Harada, A. J. Organomet. Chem. 2004, 689, 612-619. (p) Corden, J. P.; Errington, W.; Moore, P.; Partridge, M. G.; Wallbridge, M. G. H. Dalton Trans. 2004, 1846-1851.
24. For recent noteworthy examples of structural studies in solution of catalytically active titanium complexes with alkoxy or aryloxy ligands, see: (a) Finn, M. G.; Sharpless, K. B. J. Am. Chem. Soc. 1991, 113, 113-126. (b) Sasaki, C.; Nakajima, K.; Kojima, M.; Junnosuke, F. Bull. Chem. Soc. Jpn. 1991, 64, 1318-1324. Seebach, D.; Plattner, D. A.; Beck, A. K. Wang, Y. M.; Hunziker, D. Helv. Chim. Acta 1992, 75, 2171-2209. Hayashi, M.; Miyamoto, Y.; Inoue, T.; Oguni, N. J. Org. Chem. 1993, 58, 1515-1522. (e) Tonchio, M.; Licini, G.; Modena, G.; Bortolini, G.; Moro, S.; Nugent, W. A. J. Am. Chem. Soc. 1999, 121, 6258-6268. (f) Potvin, P. G.; Fieldhouse, B. G. Tetrahedron: Asymmetry 1999, 10, 1661-1672. (g) You, J.-S.; Shao, M.-Y.; Gau, H.-M. Organometallics 2000, 19, 3368-3373. (h) Flores-Lopéz, L. Z.; Parra-Hake, M.; Somanathan, R.; Walsh, P. J. Organometallics 2000, 19, 2153-2160. Sarvay, I.; Almqvist, F.; Frejd, T. Chem. Eur. J. 2001, 7, 2158-2166. (j) Hintermann, L.; Broggini, D.; Togni, A. Helv. Chim. Acta 2002, 85, 1597-1612. (k) Wu, K.-H.; Gau, H.-M. Organometallics 2003, 22, 5193-5200. Pérez, Y.; del Hierro, I.; Fajardo, M.; Otero, A. J. Organomet. Chem. 2003, 679, 220-228. Wu, K.-H.; Gau, H.-M. Organometallics 2004, 23, 580-588. (n) Ladipo, F. T.; Sarveswaran, V.; Kingston, J. V.; Huyck, R. A.; Bylikin, S. Y.; Carr, S. D.; Watts, R.; Parkin, S. J. Organomet. Chem. 2004, 689, 502-514. (o) Takashima, Y.; Nakayama, Y.; Hirao, T. ; Yasuda, H.; Harada, A. J. Organomet. Chem. 2004, 689, 612-619. (p) Corden, J. P.; Errington, W.; Moore, P.; Partridge, M. G.; Wallbridge, M. G. H. Dalton Trans. 2004, 1846-1851.
25. For recent noteworthy examples of structural studies in solution of catalytically active titanium complexes with alkoxy or aryloxy ligands, see: (a) Finn, M. G.; Sharpless, K. B. J. Am. Chem. Soc. 1991, 113, 113-126. (b) Sasaki, C.; Nakajima, K.; Kojima, M.; Junnosuke, F. Bull. Chem. Soc. Jpn. 1991, 64, 1318-1324. Seebach, D.; Plattner, D. A.; Beck, A. K. Wang, Y. M.; Hunziker, D. Helv. Chim. Acta 1992, 75, 2171-2209. Hayashi, M.; Miyamoto, Y.; Inoue, T.; Oguni, N. J. Org. Chem. 1993, 58, 1515-1522. (e) Tonchio, M.; Licini, G.; Modena, G.; Bortolini, G.; Moro, S.; Nugent, W. A. J. Am. Chem. Soc. 1999, 121, 6258-6268. (f) Potvin, P. G.; Fieldhouse, B. G. Tetrahedron: Asymmetry 1999, 10, 1661-1672. (g) You, J.-S.; Shao, M.-Y.; Gau, H.-M. Organometallics 2000, 19, 3368-3373. (h) Flores-Lopéz, L. Z.; Parra-Hake, M.; Somanathan, R.; Walsh, P. J. Organometallics 2000, 19, 2153-2160. Sarvay, I.; Almqvist, F.; Frejd, T. Chem. Eur. J. 2001, 7, 2158-2166. (j) Hintermann, L.; Broggini, D.; Togni, A. Helv. Chim. Acta 2002, 85, 1597-1612. (k) Wu, K.-H.; Gau, H.-M. Organometallics 2003, 22, 5193-5200. Pérez, Y.; del Hierro, I.; Fajardo, M.; Otero, A. J. Organomet. Chem. 2003, 679, 220-228. Wu, K.-H.; Gau, H.-M. Organometallics 2004, 23, 580-588. (n) Ladipo, F. T.; Sarveswaran, V.; Kingston, J. V.; Huyck, R. A.; Bylikin, S. Y.; Carr, S. D.; Watts, R.; Parkin, S. J. Organomet. Chem. 2004, 689, 502-514. (o) Takashima, Y.; Nakayama, Y.; Hirao, T. ; Yasuda, H.; Harada, A. J. Organomet. Chem. 2004, 689, 612-619. (p) Corden, J. P.; Errington, W.; Moore, P.; Partridge, M. G.; Wallbridge, M. G. H. Dalton Trans. 2004, 1846-1851.
26. For recent noteworthy examples of structural studies in solution of catalytically active titanium complexes with alkoxy or aryloxy ligands, see: (a) Finn, M. G.; Sharpless, K. B. J. Am. Chem. Soc. 1991, 113, 113-126. (b) Sasaki, C.; Nakajima, K.; Kojima, M.; Junnosuke, F. Bull. Chem. Soc. Jpn. 1991, 64, 1318-1324. Seebach, D.; Plattner, D. A.; Beck, A. K. Wang, Y. M.; Hunziker, D. Helv. Chim. Acta 1992, 75, 2171-2209. Hayashi, M.; Miyamoto, Y.; Inoue, T.; Oguni, N. J. Org. Chem. 1993, 58, 1515-1522. (e) Tonchio, M.; Licini, G.; Modena, G.; Bortolini, G.; Moro, S.; Nugent, W. A. J. Am. Chem. Soc. 1999, 121, 6258-6268. (f) Potvin, P. G.; Fieldhouse, B. G. Tetrahedron: Asymmetry 1999, 10, 1661-1672. (g) You, J.-S.; Shao, M.-Y.; Gau, H.-M. Organometallics 2000, 19, 3368-3373. (h) Flores-Lopéz, L. Z.; Parra-Hake, M.; Somanathan, R.; Walsh, P. J. Organometallics 2000, 19, 2153-2160. Sarvay, I.; Almqvist, F.; Frejd, T. Chem. Eur. J. 2001, 7, 2158-2166. (j) Hintermann, L.; Broggini, D.; Togni, A. Helv. Chim. Acta 2002, 85, 1597-1612. (k) Wu, K.-H.; Gau, H.-M. Organometallics 2003, 22, 5193-5200. Pérez, Y.; del Hierro, I.; Fajardo, M.; Otero, A. J. Organomet. Chem. 2003, 679, 220-228. Wu, K.-H.; Gau, H.-M. Organometallics 2004, 23, 580-588. (n) Ladipo, F. T.; Sarveswaran, V.; Kingston, J. V.; Huyck, R. A.; Bylikin, S. Y.; Carr, S. D.; Watts, R.; Parkin, S. J. Organomet. Chem. 2004, 689, 502-514. (o) Takashima, Y.; Nakayama, Y.; Hirao, T. ; Yasuda, H.; Harada, A. J. Organomet. Chem. 2004, 689, 612-619. (p) Corden, J. P.; Errington, W.; Moore, P.; Partridge, M. G.; Wallbridge, M. G. H. Dalton Trans. 2004, 1846-1851.
27. For recent noteworthy examples of structural studies in solution of catalytically active titanium complexes with alkoxy or aryloxy ligands, see: (a) Finn, M. G.; Sharpless, K. B. J. Am. Chem. Soc. 1991, 113, 113-126. (b) Sasaki, C.; Nakajima, K.; Kojima, M.; Junnosuke, F. Bull. Chem. Soc. Jpn. 1991, 64, 1318-1324. Seebach, D.; Plattner, D. A.; Beck, A. K. Wang, Y. M.; Hunziker, D. Helv. Chim. Acta 1992, 75, 2171-2209. Hayashi, M.; Miyamoto, Y.; Inoue, T.; Oguni, N. J. Org. Chem. 1993, 58, 1515-1522. (e) Tonchio, M.; Licini, G.; Modena, G.; Bortolini, G.; Moro, S.; Nugent, W. A. J. Am. Chem. Soc. 1999, 121, 6258-6268. (f) Potvin, P. G.; Fieldhouse, B. G. Tetrahedron: Asymmetry 1999, 10, 1661-1672. (g) You, J.-S.; Shao, M.-Y.; Gau, H.-M. Organometallics 2000, 19, 3368-3373. (h) Flores-Lopéz, L. Z.; Parra-Hake, M.; Somanathan, R.; Walsh, P. J. Organometallics 2000, 19, 2153-2160. Sarvay, I.; Almqvist, F.; Frejd, T. Chem. Eur. J. 2001, 7, 2158-2166. (j) Hintermann, L.; Broggini, D.; Togni, A. Helv. Chim. Acta 2002, 85, 1597-1612. (k) Wu, K.-H.; Gau, H.-M. Organometallics 2003, 22, 5193-5200. Pérez, Y.; del Hierro, I.; Fajardo, M.; Otero, A. J. Organomet. Chem. 2003, 679, 220-228. Wu, K.-H.; Gau, H.-M. Organometallics 2004, 23, 580-588. (n) Ladipo, F. T.; Sarveswaran, V.; Kingston, J. V.; Huyck, R. A.; Bylikin, S. Y.; Carr, S. D.; Watts, R.; Parkin, S. J. Organomet. Chem. 2004, 689, 502-514. (o) Takashima, Y.; Nakayama, Y.; Hirao, T. ; Yasuda, H.; Harada, A. J. Organomet. Chem. 2004, 689, 612-619. (p) Corden, J. P.; Errington, W.; Moore, P.; Partridge, M. G.; Wallbridge, M. G. H. Dalton Trans. 2004, 1846-1851.
28. For recent noteworthy examples of structural studies in solution of catalytically active titanium complexes with alkoxy or aryloxy ligands, see: (a) Finn, M. G.; Sharpless, K. B. J. Am. Chem. Soc. 1991, 113, 113-126. (b) Sasaki, C.; Nakajima, K.; Kojima, M.; Junnosuke, F. Bull. Chem. Soc. Jpn. 1991, 64, 1318-1324. Seebach, D.; Plattner, D. A.; Beck, A. K. Wang, Y. M.; Hunziker, D. Helv. Chim. Acta 1992, 75, 2171-2209. Hayashi, M.; Miyamoto, Y.; Inoue, T.; Oguni, N. J. Org. Chem. 1993, 58, 1515-1522. (e) Tonchio, M.; Licini, G.; Modena, G.; Bortolini, G.; Moro, S.; Nugent, W. A. J. Am. Chem. Soc. 1999, 121, 6258-6268. (f) Potvin, P. G.; Fieldhouse, B. G. Tetrahedron: Asymmetry 1999, 10, 1661-1672. (g) You, J.-S.; Shao, M.-Y.; Gau, H.-M. Organometallics 2000, 19, 3368-3373. (h) Flores-Lopéz, L. Z.; Parra-Hake, M.; Somanathan, R.; Walsh, P. J. Organometallics 2000, 19, 2153-2160. Sarvay, I.; Almqvist, F.; Frejd, T. Chem. Eur. J. 2001, 7, 2158-2166. (j) Hintermann, L.; Broggini, D.; Togni, A. Helv. Chim. Acta 2002, 85, 1597-1612. (k) Wu, K.-H.; Gau, H.-M. Organometallics 2003, 22, 5193-5200. Pérez, Y.; del Hierro, I.; Fajardo, M.; Otero, A. J. Organomet. Chem. 2003, 679, 220-228. Wu, K.-H.; Gau, H.-M. Organometallics 2004, 23, 580-588. (n) Ladipo, F. T.; Sarveswaran, V.; Kingston, J. V.; Huyck, R. A.; Bylikin, S. Y.; Carr, S. D.; Watts, R.; Parkin, S. J. Organomet. Chem. 2004, 689, 502-514. (o) Takashima, Y.; Nakayama, Y.; Hirao, T. ; Yasuda, H.; Harada, A. J. Organomet. Chem. 2004, 689, 612-619. (p) Corden, J. P.; Errington, W.; Moore, P.; Partridge, M. G.; Wallbridge, M. G. H. Dalton Trans. 2004, 1846-1851.
29. For recent noteworthy examples of structural studies in solution of catalytically active titanium complexes with alkoxy or aryloxy ligands, see: (a) Finn, M. G.; Sharpless, K. B. J. Am. Chem. Soc. 1991, 113, 113-126. (b) Sasaki, C.; Nakajima, K.; Kojima, M.; Junnosuke, F. Bull. Chem. Soc. Jpn. 1991, 64, 1318-1324. Seebach, D.; Plattner, D. A.; Beck, A. K. Wang, Y. M.; Hunziker, D. Helv. Chim. Acta 1992, 75, 2171-2209. Hayashi, M.; Miyamoto, Y.; Inoue, T.; Oguni, N. J. Org. Chem. 1993, 58, 1515-1522. (e) Tonchio, M.; Licini, G.; Modena, G.; Bortolini, G.; Moro, S.; Nugent, W. A. J. Am. Chem. Soc. 1999, 121, 6258-6268. (f) Potvin, P. G.; Fieldhouse, B. G. Tetrahedron: Asymmetry 1999, 10, 1661-1672. (g) You, J.-S.; Shao, M.-Y.; Gau, H.-M. Organometallics 2000, 19, 3368-3373. (h) Flores-Lopéz, L. Z.; Parra-Hake, M.; Somanathan, R.; Walsh, P. J. Organometallics 2000, 19, 2153-2160. Sarvay, I.; Almqvist, F.; Frejd, T. Chem. Eur. J. 2001, 7, 2158-2166. (j) Hintermann, L.; Broggini, D.; Togni, A. Helv. Chim. Acta 2002, 85, 1597-1612. (k) Wu, K.-H.; Gau, H.-M. Organometallics 2003, 22, 5193-5200. Pérez, Y.; del Hierro, I.; Fajardo, M.; Otero, A. J. Organomet. Chem. 2003, 679, 220-228. Wu, K.-H.; Gau, H.-M. Organometallics 2004, 23, 580-588. (n) Ladipo, F. T.; Sarveswaran, V.; Kingston, J. V.; Huyck, R. A.; Bylikin, S. Y.; Carr, S. D.; Watts, R.; Parkin, S. J. Organomet. Chem. 2004, 689, 502-514. (o) Takashima, Y.; Nakayama, Y.; Hirao, T. ; Yasuda, H.; Harada, A. J. Organomet. Chem. 2004, 689, 612-619. (p) Corden, J. P.; Errington, W.; Moore, P.; Partridge, M. G.; Wallbridge, M. G. H. Dalton Trans. 2004, 1846-1851.
30. For recent noteworthy examples of structural studies in solution of catalytically active titanium complexes with alkoxy or aryloxy ligands, see: (a) Finn, M. G.; Sharpless, K. B. J. Am. Chem. Soc. 1991, 113, 113-126. (b) Sasaki, C.; Nakajima, K.; Kojima, M.; Junnosuke, F. Bull. Chem. Soc. Jpn. 1991, 64, 1318-1324. Seebach, D.; Plattner, D. A.; Beck, A. K. Wang, Y. M.; Hunziker, D. Helv. Chim. Acta 1992, 75, 2171-2209. Hayashi, M.; Miyamoto, Y.; Inoue, T.; Oguni, N. J. Org. Chem. 1993, 58, 1515-1522. (e) Tonchio, M.; Licini, G.; Modena, G.; Bortolini, G.; Moro, S.; Nugent, W. A. J. Am. Chem. Soc. 1999, 121, 6258-6268. (f) Potvin, P. G.; Fieldhouse, B. G. Tetrahedron: Asymmetry 1999, 10, 1661-1672. (g) You, J.-S.; Shao, M.-Y.; Gau, H.-M. Organometallics 2000, 19, 3368-3373. (h) Flores-Lopéz, L. Z.; Parra-Hake, M.; Somanathan, R.; Walsh, P. J. Organometallics 2000, 19, 2153-2160. Sarvay, I.; Almqvist, F.; Frejd, T. Chem. Eur. J. 2001, 7, 2158-2166. (j) Hintermann, L.; Broggini, D.; Togni, A. Helv. Chim. Acta 2002, 85, 1597-1612. (k) Wu, K.-H.; Gau, H.-M. Organometallics 2003, 22, 5193-5200. Pérez, Y.; del Hierro, I.; Fajardo, M.; Otero, A. J. Organomet. Chem. 2003, 679, 220-228. Wu, K.-H.; Gau, H.-M. Organometallics 2004, 23, 580-588. (n) Ladipo, F. T.; Sarveswaran, V.; Kingston, J. V.; Huyck, R. A.; Bylikin, S. Y.; Carr, S. D.; Watts, R.; Parkin, S. J. Organomet. Chem. 2004, 689, 502-514. (o) Takashima, Y.; Nakayama, Y.; Hirao, T. ; Yasuda, H.; Harada, A. J. Organomet. Chem. 2004, 689, 612-619. (p) Corden, J. P.; Errington, W.; Moore, P.; Partridge, M. G.; Wallbridge, M. G. H. Dalton Trans. 2004, 1846-1851.
31. For recent noteworthy examples of structural studies in solution of catalytically active titanium complexes with alkoxy or aryloxy ligands, see: (a) Finn, M. G.; Sharpless, K. B. J. Am. Chem. Soc. 1991, 113, 113-126. (b) Sasaki, C.; Nakajima, K.; Kojima, M.; Junnosuke, F. Bull. Chem. Soc. Jpn. 1991, 64, 1318-1324. Seebach, D.; Plattner, D. A.; Beck, A. K. Wang, Y. M.; Hunziker, D. Helv. Chim. Acta 1992, 75, 2171-2209. Hayashi, M.; Miyamoto, Y.; Inoue, T.; Oguni, N. J. Org. Chem. 1993, 58, 1515-1522. (e) Tonchio, M.; Licini, G.; Modena, G.; Bortolini, G.; Moro, S.; Nugent, W. A. J. Am. Chem. Soc. 1999, 121, 6258-6268. (f) Potvin, P. G.; Fieldhouse, B. G. Tetrahedron: Asymmetry 1999, 10, 1661-1672. (g) You, J.-S.; Shao, M.-Y.; Gau, H.-M. Organometallics 2000, 19, 3368-3373. (h) Flores-Lopéz, L. Z.; Parra-Hake, M.; Somanathan, R.; Walsh, P. J. Organometallics 2000, 19, 2153-2160. Sarvay, I.; Almqvist, F.; Frejd, T. Chem. Eur. J. 2001, 7, 2158-2166. (j) Hintermann, L.; Broggini, D.; Togni, A. Helv. Chim. Acta 2002, 85, 1597-1612. (k) Wu, K.-H.; Gau, H.-M. Organometallics 2003, 22, 5193-5200. Pérez, Y.; del Hierro, I.; Fajardo, M.; Otero, A. J. Organomet. Chem. 2003, 679, 220-228. Wu, K.-H.; Gau, H.-M. Organometallics 2004, 23, 580-588. (n) Ladipo, F. T.; Sarveswaran, V.; Kingston, J. V.; Huyck, R. A.; Bylikin, S. Y.; Carr, S. D.; Watts, R.; Parkin, S. J. Organomet. Chem. 2004, 689, 502-514. (o) Takashima, Y.; Nakayama, Y.; Hirao, T. ; Yasuda, H.; Harada, A. J. Organomet. Chem. 2004, 689, 612-619. (p) Corden, J. P.; Errington, W.; Moore, P.; Partridge, M. G.; Wallbridge, M. G. H. Dalton Trans. 2004, 1846-1851.
32. For recent noteworthy examples of structural studies in solution of catalytically active titanium complexes with alkoxy or aryloxy ligands, see: (a) Finn, M. G.; Sharpless, K. B. J. Am. Chem. Soc. 1991, 113, 113-126. (b) Sasaki, C.; Nakajima, K.; Kojima, M.; Junnosuke, F. Bull. Chem. Soc. Jpn. 1991, 64, 1318-1324. Seebach, D.; Plattner, D. A.; Beck, A. K. Wang, Y. M.; Hunziker, D. Helv. Chim. Acta 1992, 75, 2171-2209. Hayashi, M.; Miyamoto, Y.; Inoue, T.; Oguni, N. J. Org. Chem. 1993, 58, 1515-1522. (e) Tonchio, M.; Licini, G.; Modena, G.; Bortolini, G.; Moro, S.; Nugent, W. A. J. Am. Chem. Soc. 1999, 121, 6258-6268. (f) Potvin, P. G.; Fieldhouse, B. G. Tetrahedron: Asymmetry 1999, 10, 1661-1672. (g) You, J.-S.; Shao, M.-Y.; Gau, H.-M. Organometallics 2000, 19, 3368-3373. (h) Flores-Lopéz, L. Z.; Parra-Hake, M.; Somanathan, R.; Walsh, P. J. Organometallics 2000, 19, 2153-2160. Sarvay, I.; Almqvist, F.; Frejd, T. Chem. Eur. J. 2001, 7, 2158-2166. (j) Hintermann, L.; Broggini, D.; Togni, A. Helv. Chim. Acta 2002, 85, 1597-1612. (k) Wu, K.-H.; Gau, H.-M. Organometallics 2003, 22, 5193-5200. Pérez, Y.; del Hierro, I.; Fajardo, M.; Otero, A. J. Organomet. Chem. 2003, 679, 220-228. Wu, K.-H.; Gau, H.-M. Organometallics 2004, 23, 580-588. (n) Ladipo, F. T.; Sarveswaran, V.; Kingston, J. V.; Huyck, R. A.; Bylikin, S. Y.; Carr, S. D.; Watts, R.; Parkin, S. J. Organomet. Chem. 2004, 689, 502-514. (o) Takashima, Y.; Nakayama, Y.; Hirao, T. ; Yasuda, H.; Harada, A. J. Organomet. Chem. 2004, 689, 612-619. (p) Corden, J. P.; Errington, W.; Moore, P.; Partridge, M. G.; Wallbridge, M. G. H. Dalton Trans. 2004, 1846-1851.
33. For recent noteworthy examples of structural studies in solution of catalytically active titanium complexes with alkoxy or aryloxy ligands, see: (a) Finn, M. G.; Sharpless, K. B. J. Am. Chem. Soc. 1991, 113, 113-126. (b) Sasaki, C.; Nakajima, K.; Kojima, M.; Junnosuke, F. Bull. Chem. Soc. Jpn. 1991, 64, 1318-1324. Seebach, D.; Plattner, D. A.; Beck, A. K. Wang, Y. M.; Hunziker, D. Helv. Chim. Acta 1992, 75, 2171-2209. Hayashi, M.; Miyamoto, Y.; Inoue, T.; Oguni, N. J. Org. Chem. 1993, 58, 1515-1522. (e) Tonchio, M.; Licini, G.; Modena, G.; Bortolini, G.; Moro, S.; Nugent, W. A. J. Am. Chem. Soc. 1999, 121, 6258-6268. (f) Potvin, P. G.; Fieldhouse, B. G. Tetrahedron: Asymmetry 1999, 10, 1661-1672. (g) You, J.-S.; Shao, M.-Y.; Gau, H.-M. Organometallics 2000, 19, 3368-3373. (h) Flores-Lopéz, L. Z.; Parra-Hake, M.; Somanathan, R.; Walsh, P. J. Organometallics 2000, 19, 2153-2160. Sarvay, I.; Almqvist, F.; Frejd, T. Chem. Eur. J. 2001, 7, 2158-2166. (j) Hintermann, L.; Broggini, D.; Togni, A. Helv. Chim. Acta 2002, 85, 1597-1612. (k) Wu, K.-H.; Gau, H.-M. Organometallics 2003, 22, 5193-5200. Pérez, Y.; del Hierro, I.; Fajardo, M.; Otero, A. J. Organomet. Chem. 2003, 679, 220-228. Wu, K.-H.; Gau, H.-M. Organometallics 2004, 23, 580-588. (n) Ladipo, F. T.; Sarveswaran, V.; Kingston, J. V.; Huyck, R. A.; Bylikin, S. Y.; Carr, S. D.; Watts, R.; Parkin, S. J. Organomet. Chem. 2004, 689, 502-514. (o) Takashima, Y.; Nakayama, Y.; Hirao, T. ; Yasuda, H.; Harada, A. J. Organomet. Chem. 2004, 689, 612-619. (p) Corden, J. P.; Errington, W.; Moore, P.; Partridge, M. G.; Wallbridge, M. G. H. Dalton Trans. 2004, 1846-1851.
34. For recent noteworthy examples of structural studies in solution of catalytically active titanium complexes with alkoxy or aryloxy ligands, see: (a) Finn, M. G.; Sharpless, K. B. J. Am. Chem. Soc. 1991, 113, 113-126. (b) Sasaki, C.; Nakajima, K.; Kojima, M.; Junnosuke, F. Bull. Chem. Soc. Jpn. 1991, 64, 1318-1324. Seebach, D.; Plattner, D. A.; Beck, A. K. Wang, Y. M.; Hunziker, D. Helv. Chim. Acta 1992, 75, 2171-2209. Hayashi, M.; Miyamoto, Y.; Inoue, T.; Oguni, N. J. Org. Chem. 1993, 58, 1515-1522. (e) Tonchio, M.; Licini, G.; Modena, G.; Bortolini, G.; Moro, S.; Nugent, W. A. J. Am. Chem. Soc. 1999, 121, 6258-6268. (f) Potvin, P. G.; Fieldhouse, B. G. Tetrahedron: Asymmetry 1999, 10, 1661-1672. (g) You, J.-S.; Shao, M.-Y.; Gau, H.-M. Organometallics 2000, 19, 3368-3373. (h) Flores-Lopéz, L. Z.; Parra-Hake, M.; Somanathan, R.; Walsh, P. J. Organometallics 2000, 19, 2153-2160. Sarvay, I.; Almqvist, F.; Frejd, T. Chem. Eur. J. 2001, 7, 2158-2166. (j) Hintermann, L.; Broggini, D.; Togni, A. Helv. Chim. Acta 2002, 85, 1597-1612. (k) Wu, K.-H.; Gau, H.-M. Organometallics 2003, 22, 5193-5200. Pérez, Y.; del Hierro, I.; Fajardo, M.; Otero, A. J. Organomet. Chem. 2003, 679, 220-228. Wu, K.-H.; Gau, H.-M. Organometallics 2004, 23, 580-588. (n) Ladipo, F. T.; Sarveswaran, V.; Kingston, J. V.; Huyck, R. A.; Bylikin, S. Y.; Carr, S. D.; Watts, R.; Parkin, S. J. Organomet. Chem. 2004, 689, 502-514. (o) Takashima, Y.; Nakayama, Y.; Hirao, T. ; Yasuda, H.; Harada, A. J. Organomet. Chem. 2004, 689, 612-619. (p) Corden, J. P.; Errington, W.; Moore, P.; Partridge, M. G.; Wallbridge, M. G. H. Dalton Trans. 2004, 1846-1851.
35. Martin, C. Ph.D. Thesis, MIT, Cambridge, 1989.
36. Other BINOL-titanium complexes, closely related to the present ones, have been investigated in the solution state: (a) Boyle, T. J.; Eilerts, N. W.; Heppert, J. A.; Takusagawa, F. Organometallics 1994, 13, 2218-2229. (b) Kitamoto, D.; Imma, H.; Nakai, T. Tetrahedron Lett. 1995, 36, 1861-1864. Terada, M.; Matsumoto, Y.; Nakamura, Y.; Mikami, K. Inorg. Chim. Acta 1999, 296, 267-272. Keck, G. E.; Krishnamurthy, D. J. Am. Chem. Soc. 1995, 117, 2363-2364. (e) Harada, T.; Hiraoka, Y.; Kusukawa, T.; Marutani, Y.; Matsui, S.; Nakatsugawa, M.; Kanda, K. Org. Lett. 2003, 5, 5059-5062.
37. Other BINOL-titanium complexes, closely related to the present ones, have been investigated in the solution state: (a) Boyle, T. J.; Eilerts, N. W.; Heppert, J. A.; Takusagawa, F. Organometallics 1994, 13, 2218-2229. (b) Kitamoto, D.; Imma, H.; Nakai, T. Tetrahedron Lett. 1995, 36, 1861-1864. Terada, M.; Matsumoto, Y.; Nakamura, Y.; Mikami, K. Inorg. Chim. Acta 1999, 296, 267-272. Keck, G. E.; Krishnamurthy, D. J. Am. Chem. Soc. 1995, 117, 2363-2364. (e) Harada, T.; Hiraoka, Y.; Kusukawa, T.; Marutani, Y.; Matsui, S.; Nakatsugawa, M.; Kanda, K. Org. Lett. 2003, 5, 5059-5062.
38. Other BINOL-titanium complexes, closely related to the present ones, have been investigated in the solution state: (a) Boyle, T. J.; Eilerts, N. W.; Heppert, J. A.; Takusagawa, F. Organometallics 1994, 13, 2218-2229. (b) Kitamoto, D.; Imma, H.; Nakai, T. Tetrahedron Lett. 1995, 36, 1861-1864. Terada, M.; Matsumoto, Y.; Nakamura, Y.; Mikami, K. Inorg. Chim. Acta 1999, 296, 267-272. Keck, G. E.; Krishnamurthy, D. J. Am. Chem. Soc. 1995, 117, 2363-2364. (e) Harada, T.; Hiraoka, Y.; Kusukawa, T.; Marutani, Y.; Matsui, S.; Nakatsugawa, M.; Kanda, K. Org. Lett. 2003, 5, 5059-5062.
39. Other BINOL-titanium complexes, closely related to the present ones, have been investigated in the solution state: (a) Boyle, T. J.; Eilerts, N. W.; Heppert, J. A.; Takusagawa, F. Organometallics 1994, 13, 2218-2229. (b) Kitamoto, D.; Imma, H.; Nakai, T. Tetrahedron Lett. 1995, 36, 1861-1864. Terada, M.; Matsumoto, Y.; Nakamura, Y.; Mikami, K. Inorg. Chim. Acta 1999, 296, 267-272. Keck, G. E.; Krishnamurthy, D. J. Am. Chem. Soc. 1995, 117, 2363-2364. (e) Harada, T.; Hiraoka, Y.; Kusukawa, T.; Marutani, Y.; Matsui, S.; Nakatsugawa, M.; Kanda, K. Org. Lett. 2003, 5, 5059-5062.
40. Other BINOL-titanium complexes, closely related to the present ones, have been investigated in the solution state: (a) Boyle, T. J.; Eilerts, N. W.; Heppert, J. A.; Takusagawa, F. Organometallics 1994, 13, 2218-2229. (b) Kitamoto, D.; Imma, H.; Nakai, T. Tetrahedron Lett. 1995, 36, 1861-1864. Terada, M.; Matsumoto, Y.; Nakamura, Y.; Mikami, K. Inorg. Chim. Acta 1999, 296, 267-272. Keck, G. E.; Krishnamurthy, D. J. Am. Chem. Soc. 1995, 117, 2363-2364. (e) Harada, T.; Hiraoka, Y.; Kusukawa, T.; Marutani, Y.; Matsui, S.; Nakatsugawa, M.; Kanda, K. Org. Lett. 2003, 5, 5059-5062.
41. 4,7,8,11
42. Di Bari, L.; Pesoitelli, G.; Pizzanelli, S.; Rosini, C.; Salvadori, P. Stereochemical study of 1,1′-binaphthyl derivatives by means of UVI CD and NMR spectroscopies; Abstracts, 10th International Symposium on Chiral Discrimination-ISCD'98; 1998, Aug 30-Sep 3; Vienna, Austria.
43. (a) Girard, C.; Kagan, H. B. Angew. Chem., Int. Ed. 1998, 37, 2922-2959.
44. (b) Blackmond, D. G. Acc. Chem. Res. 2000, 33, 402-411.
45. -1. Experimental NOEs varied between 2 and 2.7 (±0.2) for species I and 2.0-2.4 (±0.2) for species II, with a similar average value of 2.3 (see Supporting Information, Table S1).
46. -1. Apart from a systematic overestimation due to the approximations used, it is clear that the two last values for each set (I.dim and II) are in good agreement, relatively speaking, with the experimental ones for species I and II (see text).
47. 4 protons are positioned in a region subjected to strong diamagnetic aniaotropy (shielding effect).
48. 4 concentration was calculated as the difference from the total quantity, since titanium-containing species other than I and II are negligible.
49. (a) Mason, S. F.; Seal, R. H.; Roberts, D. R. Tetrahedron 1974, 30, 1671-1682.
50. (b) Di Bari, L.; Pescitelli, G.; Salvadori, P. J. Am. Chem. Soc. 1999, 121, 7998-8004.
51. (c) Di Bari, L.; Pescitelli, G.; Marchetti, F.; Salvadori, P. J. Am. Chem. Soc. 2000, 122, 6395-6398.
52. (d) Rosini, C.; Superchi, S.; Peerlings, H. W. I.; Meijer, E. W. Eur. J. Org. Chem. 2000, 61-71.
53. (e) Di Bari, L.; Pescitelli, G.; Reginato, G.; Salvadori, P. Chirality 2001, 13, 348-555.
54. (f) Di Bari, L.; Lelli, M.; Pintacuda, G.; Pescitelli, G.; Marchetti, F. ; Salvadori, P. J. Am. Chem. Soc. 2003, 125, 5549-5558.
55. Hanazaki, I.; Akimoto, H. J. Am. Chem. Soc. 1972, 94, 4102-4106.
56. The different concentration and solvent used must be kept in mind when comparing NMR and CD spectra.
57. b bands, passing from BINOL to its titanium complexes, should have a mainly electronic origin, since a similar feature is obtained by dissolving BINOL in a 0.1 M NaOH water solution.
58. 20b It was extracted by deconvoluting experimental spectra by means of the Fourier self-deconvolution (FSD) method (Kauppinen, J. K.; Moffatt, D. J.; Mantsch, H. H.; Cameron, D. G. Appl. Spectrosc. 1981, 35, 271-276), checking self-consistency upon varying the estimated bandwidth. The FSD routine is integrated in Jasco Spectra Analysis Software, v. 1.51.
59. 20e,f
60. Johnson, C. S., Jr. Prog. Nucl. Magn. Reson. Spectrosc. 1999, 34, 203-256.