First Synthesis and Structural Characterization of an Enantiomerically Pure Planar-Chiral Lewis Acid Complex

Journal of Organic Chemistry

Volumn 62, Issue 24, 1997, Pages 8286-8287

  Tweddell, Jennifer ^a   Hoic, Diego A ^a   Fu, Gregory C ^a  

^a MASSACHUSETTS INSTITUTE OF TECHNOLOGY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000984665     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo971757k     Document Type: Article

References (30)

1. For early work, see: (a) Hashimoto, S.; Komeshima, N.; Koga, K. J. Chem. Soc., Chem. Commun. 1979, 437-438. (b) Bednarski, M.; Danishefsky, S. J. Am. Chem. Soc. 1983, 105, 3716-3717.
2. For early work, see: (a) Hashimoto, S.; Komeshima, N.; Koga, K. J. Chem. Soc., Chem. Commun. 1979, 437-438. (b) Bednarski, M.; Danishefsky, S. J. Am. Chem. Soc. 1983, 105, 3716-3717.
3. For recent reviews, see: (a) Ishihara, K.; Yamamoto, H. In Advances in Catalytic Processes; Doyle, M. P., Ed.; JAI: Greenwich, CT, 1995; Vol. 1, pp 29-59. (b) Deloux, L.; Srebnik, M. Chem. Rev. 1993, 93, 763-784. Narasaka, K. Synthesis 1991, 1-11.
4. For recent reviews, see: (a) Ishihara, K.; Yamamoto, H. In Advances in Catalytic Processes; Doyle, M. P., Ed.; JAI: Greenwich, CT, 1995; Vol. 1, pp 29-59. (b) Deloux, L.; Srebnik, M. Chem. Rev. 1993, 93, 763-784. Narasaka, K. Synthesis 1991, 1-11.
5. For recent reviews, see: (a) Ishihara, K.; Yamamoto, H. In Advances in Catalytic Processes; Doyle, M. P., Ed.; JAI: Greenwich, CT, 1995; Vol. 1, pp 29-59. (b) Deloux, L.; Srebnik, M. Chem. Rev. 1993, 93, 763-784. Narasaka, K. Synthesis 1991, 1-11.
6. Amendola, M. C.; Stockman, K. E.; Hoic, D. A.; Davis, W. M.; Fu, G. C. Angew. Chem., Int. Ed. Engl. 1997, 36, 267-269.
7. 3, see: Alexakis, A.; Mangeney, P.; Marek, I.; Rose-Munch, F.; Rose, E.; Semra, A.; Robert, F. J. Am. Chem. Soc. 1992, 114, 8288-8290.
8. For previous reports of the synthesis of neutral borabenzene ligand adducts, see: (a) Boese, R.; Finke, N.; Henkelmann, J.; Maier, G.; Paetzold, P.; Reisenauer, H. P.; Schmid, G. Chem. Ber. 1985, 118, 1644-1654, (b) Boese, R.; Finke, N.; Keil, T.; Paetzold, P.; Schmid, G. Z. Naturforsch., B 1985, 40, 1327-1332. Hoic, D. A.; Wolf, J. R.; Davis, W. M.; Fu, G. C. Organometallics 1996, 15, 1315-1318. Reference 3.
9. For previous reports of the synthesis of neutral borabenzene ligand adducts, see: (a) Boese, R.; Finke, N.; Henkelmann, J.; Maier, G.; Paetzold, P.; Reisenauer, H. P.; Schmid, G. Chem. Ber. 1985, 118, 1644-1654, (b) Boese, R.; Finke, N.; Keil, T.; Paetzold, P.; Schmid, G. Z. Naturforsch., B 1985, 40, 1327-1332. Hoic, D. A.; Wolf, J. R.; Davis, W. M.; Fu, G. C. Organometallics 1996, 15, 1315-1318. Reference 3.
10. For previous reports of the synthesis of neutral borabenzene ligand adducts, see: (a) Boese, R.; Finke, N.; Henkelmann, J.; Maier, G.; Paetzold, P.; Reisenauer, H. P.; Schmid, G. Chem. Ber. 1985, 118, 1644-1654, (b) Boese, R.; Finke, N.; Keil, T.; Paetzold, P.; Schmid, G. Z. Naturforsch., B 1985, 40, 1327-1332. Hoic, D. A.; Wolf, J. R.; Davis, W. M.; Fu, G. C. Organometallics 1996, 15, 1315-1318. Reference 3.
11. For previous reports of the synthesis of neutral borabenzene ligand adducts, see: (a) Boese, R.; Finke, N.; Henkelmann, J.; Maier, G.; Paetzold, P.; Reisenauer, H. P.; Schmid, G. Chem. Ber. 1985, 118, 1644-1654, (b) Boese, R.; Finke, N.; Keil, T.; Paetzold, P.; Schmid, G. Z. Naturforsch., B 1985, 40, 1327-1332. Hoic, D. A.; Wolf, J. R.; Davis, W. M.; Fu, G. C. Organometallics 1996, 15, 1315-1318. Reference 3.
12. (a) Ashe, A. J., III; Chan, W.-T.; Smith, T. W.; Taba, K. M. J. Org. Chem. 1981, 46, 881-885.
13. (b) Reference 5c.
14. For related work, see: Jutzi, P.; Baumgartner, J. J. Organomet. Chem. 1978, 148, 247-255.
15. Amendola, M. C. M. S. Thesis, Massachusetts Institute of Technology, 1995. We thank Dr. Kenneth E. Stockman for optimizing the synthesis of 4 and 5.
16. 1H NMR spectra were obtained at room temperature and at -78 °C.
17. For details regarding the X-ray crystal structure of adduct 6, see the Supporting Information.
18. We thank Prof. Bruce Tidor and Justin A. Caravella (MIT) for performing these calculations.
19. 3 to other (2-(trimethylsilyl)borabenzene)-L* adducts (L* = tertiary amines, other oxazolines).
20. Based on a search of the Cambridge Crystallographic Database.
21. Based on a search of the Cambridge Crystallographic Database, (a) 1.52 Å: Siriwardane, U.; Chu, S. S. C.; Hosmane, N. S.; Zhang, G.; Zhu, W.; Zhu, H. Acta Crystallogr., Sect. C 1989, 45, 294-297. (b) 1.63 Å: Koster, R.; Kucznierz, R.; Schussler, W.; Blaser, D.; Boese, R. Liebigs Ann. Chem. 1993, 189-200.
22. Based on a search of the Cambridge Crystallographic Database, (a) 1.52 Å: Siriwardane, U.; Chu, S. S. C.; Hosmane, N. S.; Zhang, G.; Zhu, W.; Zhu, H. Acta Crystallogr., Sect. C 1989, 45, 294-297. (b) 1.63 Å: Koster, R.; Kucznierz, R.; Schussler, W.; Blaser, D.; Boese, R. Liebigs Ann. Chem. 1993, 189-200.
23. We suspect that "free" (no 1-substituent) borabenzene derivatives will be extremely challenging to isolate. See: (a) Schulman, J. M.; Disch, R. L.; Sabio, M. I. J. Am. Chem. Soc. 1982, 104, 3785-3788. (b) Raabe, G.; Heyne, E.; Schleker, W.; Fleischhauer, J. Z. Naturforsch., A 1984, 39, 678-681. Maier, G. Pure Appl. Chem. 1986, 58, 95-104. Raabe, G.; Schleker, W.; Heyne, E.; Fleischhauer, J. Z. Naturforsch., A 1987, 42, 352-360. (e) Maier, G.; Reisenauer, H. P.; Henkelmann, J.; Kliche, C. Angew. Chem., Int. Ed. Engl. 1988, 27, 295-296. (f) Schulman, J. M.; Disch, R. L. Organometallics 1989, 8, 733-737. (g) Cioslowski, J.; Hay, P. J. J. Am. Chem. Soc. 1990, 112, 1707-1710. (h) Maier, G.; Wolf, H.-J.; Boese, R. Chem. Ber. 1990, 123, 505-511.
24. We suspect that "free" (no 1-substituent) borabenzene derivatives will be extremely challenging to isolate. See: (a) Schulman, J. M.; Disch, R. L.; Sabio, M. I. J. Am. Chem. Soc. 1982, 104, 3785-3788. (b) Raabe, G.; Heyne, E.; Schleker, W.; Fleischhauer, J. Z. Naturforsch., A 1984, 39, 678-681. Maier, G. Pure Appl. Chem. 1986, 58, 95-104. Raabe, G.; Schleker, W.; Heyne, E.; Fleischhauer, J. Z. Naturforsch., A 1987, 42, 352-360. (e) Maier, G.; Reisenauer, H. P.; Henkelmann, J.; Kliche, C. Angew. Chem., Int. Ed. Engl. 1988, 27, 295-296. (f) Schulman, J. M.; Disch, R. L. Organometallics 1989, 8, 733-737. (g) Cioslowski, J.; Hay, P. J. J. Am. Chem. Soc. 1990, 112, 1707-1710. (h) Maier, G.; Wolf, H.-J.; Boese, R. Chem. Ber. 1990, 123, 505-511.
25. We suspect that "free" (no 1-substituent) borabenzene derivatives will be extremely challenging to isolate. See: (a) Schulman, J. M.; Disch, R. L.; Sabio, M. I. J. Am. Chem. Soc. 1982, 104, 3785-3788. (b) Raabe, G.; Heyne, E.; Schleker, W.; Fleischhauer, J. Z. Naturforsch., A 1984, 39, 678-681. Maier, G. Pure Appl. Chem. 1986, 58, 95-104. Raabe, G.; Schleker, W.; Heyne, E.; Fleischhauer, J. Z. Naturforsch., A 1987, 42, 352-360. (e) Maier, G.; Reisenauer, H. P.; Henkelmann, J.; Kliche, C. Angew. Chem., Int. Ed. Engl. 1988, 27, 295-296. (f) Schulman, J. M.; Disch, R. L. Organometallics 1989, 8, 733-737. (g) Cioslowski, J.; Hay, P. J. J. Am. Chem. Soc. 1990, 112, 1707-1710. (h) Maier, G.; Wolf, H.-J.; Boese, R. Chem. Ber. 1990, 123, 505-511.
26. We suspect that "free" (no 1-substituent) borabenzene derivatives will be extremely challenging to isolate. See: (a) Schulman, J. M.; Disch, R. L.; Sabio, M. I. J. Am. Chem. Soc. 1982, 104, 3785-3788. (b) Raabe, G.; Heyne, E.; Schleker, W.; Fleischhauer, J. Z. Naturforsch., A 1984, 39, 678-681. Maier, G. Pure Appl. Chem. 1986, 58, 95-104. Raabe, G.; Schleker, W.; Heyne, E.; Fleischhauer, J. Z. Naturforsch., A 1987, 42, 352-360. (e) Maier, G.; Reisenauer, H. P.; Henkelmann, J.; Kliche, C. Angew. Chem., Int. Ed. Engl. 1988, 27, 295-296. (f) Schulman, J. M.; Disch, R. L. Organometallics 1989, 8, 733-737. (g) Cioslowski, J.; Hay, P. J. J. Am. Chem. Soc. 1990, 112, 1707-1710. (h) Maier, G.; Wolf, H.-J.; Boese, R. Chem. Ber. 1990, 123, 505-511.
27. We suspect that "free" (no 1-substituent) borabenzene derivatives will be extremely challenging to isolate. See: (a) Schulman, J. M.; Disch, R. L.; Sabio, M. I. J. Am. Chem. Soc. 1982, 104, 3785-3788. (b) Raabe, G.; Heyne, E.; Schleker, W.; Fleischhauer, J. Z. Naturforsch., A 1984, 39, 678-681. Maier, G. Pure Appl. Chem. 1986, 58, 95-104. Raabe, G.; Schleker, W.; Heyne, E.; Fleischhauer, J. Z. Naturforsch., A 1987, 42, 352-360. (e) Maier, G.; Reisenauer, H. P.; Henkelmann, J.; Kliche, C. Angew. Chem., Int. Ed. Engl. 1988, 27, 295-296. (f) Schulman, J. M.; Disch, R. L. Organometallics 1989, 8, 733-737. (g) Cioslowski, J.; Hay, P. J. J. Am. Chem. Soc. 1990, 112, 1707-1710. (h) Maier, G.; Wolf, H.-J.; Boese, R. Chem. Ber. 1990, 123, 505-511.
28. We suspect that "free" (no 1-substituent) borabenzene derivatives will be extremely challenging to isolate. See: (a) Schulman, J. M.; Disch, R. L.; Sabio, M. I. J. Am. Chem. Soc. 1982, 104, 3785-3788. (b) Raabe, G.; Heyne, E.; Schleker, W.; Fleischhauer, J. Z. Naturforsch., A 1984, 39, 678-681. Maier, G. Pure Appl. Chem. 1986, 58, 95-104. Raabe, G.; Schleker, W.; Heyne, E.; Fleischhauer, J. Z. Naturforsch., A 1987, 42, 352-360. (e) Maier, G.; Reisenauer, H. P.; Henkelmann, J.; Kliche, C. Angew. Chem., Int. Ed. Engl. 1988, 27, 295-296. (f) Schulman, J. M.; Disch, R. L. Organometallics 1989, 8, 733-737. (g) Cioslowski, J.; Hay, P. J. J. Am. Chem. Soc. 1990, 112, 1707-1710. (h) Maier, G.; Wolf, H.-J.; Boese, R. Chem. Ber. 1990, 123, 505-511.
29. We suspect that "free" (no 1-substituent) borabenzene derivatives will be extremely challenging to isolate. See: (a) Schulman, J. M.; Disch, R. L.; Sabio, M. I. J. Am. Chem. Soc. 1982, 104, 3785-3788. (b) Raabe, G.; Heyne, E.; Schleker, W.; Fleischhauer, J. Z. Naturforsch., A 1984, 39, 678-681. Maier, G. Pure Appl. Chem. 1986, 58, 95-104. Raabe, G.; Schleker, W.; Heyne, E.; Fleischhauer, J. Z. Naturforsch., A 1987, 42, 352-360. (e) Maier, G.; Reisenauer, H. P.; Henkelmann, J.; Kliche, C. Angew. Chem., Int. Ed. Engl. 1988, 27, 295-296. (f) Schulman, J. M.; Disch, R. L. Organometallics 1989, 8, 733-737. (g) Cioslowski, J.; Hay, P. J. J. Am. Chem. Soc. 1990, 112, 1707-1710. (h) Maier, G.; Wolf, H.-J.; Boese, R. Chem. Ber. 1990, 123, 505-511.
30. We suspect that "free" (no 1-substituent) borabenzene derivatives will be extremely challenging to isolate. See: (a) Schulman, J. M.; Disch, R. L.; Sabio, M. I. J. Am. Chem. Soc. 1982, 104, 3785-3788. (b) Raabe, G.; Heyne, E.; Schleker, W.; Fleischhauer, J. Z. Naturforsch., A 1984, 39, 678-681. Maier, G. Pure Appl. Chem. 1986, 58, 95-104. Raabe, G.; Schleker, W.; Heyne, E.; Fleischhauer, J. Z. Naturforsch., A 1987, 42, 352-360. (e) Maier, G.; Reisenauer, H. P.; Henkelmann, J.; Kliche, C. Angew. Chem., Int. Ed. Engl. 1988, 27, 295-296. (f) Schulman, J. M.; Disch, R. L. Organometallics 1989, 8, 733-737. (g) Cioslowski, J.; Hay, P. J. J. Am. Chem. Soc. 1990, 112, 1707-1710. (h) Maier, G.; Wolf, H.-J.; Boese, R. Chem. Ber. 1990, 123, 505-511.