Lithium ephedrate-mediated addition of a lithium acetylide to a ketone: Solution structures and relative reactivities of mixed aggregates underlying the high enantioselectivities

Journal of the American Chemical Society

Volumn 120, Issue 9, 1998, Pages 2028-2038

  Thompson, Andrew ^a   Corley, Edward G ^a   Huntington, Martha F ^a   Grabowski, Edward J J ^a   Remenar, Julius F ^b   Collum, David B ^b  

^a MERCK RESEARCH LABORATORIES   (United States)

^b Department of Molecular Biology and Genetics   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

6 CHLORO 4 CYCLOPROPYL 3,4 DIHYDRO 4 [(2 PYRIDYL)ETHYNYL] 2(1H) QUINAZOLINONE; DMP 299; EFAVIRENZ; KETONE; LITHIUM ACETYLIDE; LITHIUM EPHEDRATE; ORGANOLITHIUM COMPOUND; RNA DIRECTED DNA POLYMERASE INHIBITOR; UNCLASSIFIED DRUG;

ACQUIRED IMMUNE DEFICIENCY SYNDROME; ARTICLE; CHEMICAL STRUCTURE; ENANTIOMER; LOW TEMPERATURE; NUCLEAR MAGNETIC RESONANCE; ORGANIC CHEMISTRY; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0032507282     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja9713791     Document Type: Article

References (144)

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40. Attempts to correlate organolithium structure with reaction stereochemistry have been described. Hilmersson, G.; Davidsson, O. J. Organomet. Chem. 1995, 489, 175. Boche, G. Angew. Chem., Int. Ed. Engl. 1989, 28, 277. Hilmersson, G.; Ahlberg, P.; Davidsson, O. J. Am. Chem. Soc. 1996, 118, 3539. Gallagher, D. J.; Kerrick, S. T.; Beak, P. J. Am. Chem. Soc. 1992, 114, 5872. Byrne, L. T.; Engelhardt, L. M.; Jacobsen, G. E.; Leung, W.-P.; Papasergio, R. I.; Raston, C. L.; Skelton, B. W.; Twiss, P.; White, A. H. J. Chem. Soc., Dalton Trans. 1989, 105, Gais, H.-J.; Dingerdissen, U.; Krüger, C.; Angermund, K. J. Am. Chem. Soc. 1987, 109, 3775. Zaegel, F.; Gallucci, J. C.; Meunier, P.; Gautheron, B.; Sivik, M. R.; Paquette, L. A. J. Am. Chem. Soc. 1994, 116, 6466. Cramer, C. J.; Denmark, S. E.; Miller, P. C.; Dorow, R. L.; Swiss, K. A.; Wilson, S. R. J. Am. Chem. Soc. 1994, 116, 2437. Williard, P. G.; Tata, J. R.; Schlessinger, R. H.; Adams, A. D.; Iwanowicz, E. J. J. Am. Chem. Soc. 1988, 110, 7901. Kahne, D.; Gut, S.; DePue, R.; Mohamadi, F.; Wanat, R. A.; Collum, D. B.; Clardy, J.; Van Duyne, G. J. Am. Chem. Soc. 1984, 106, 4685. Wanat, R. A.; Collum, D. B. J. Am. Chem. Soc. 1985, 107, 2078. Galiano-Roth, A. S.; Collum, D. B. J. Am. Chem. Soc. 1988, 110, 3546. Seebach, D.; Bauer, W.; Hansen, J.; Laube, T.; Schweizer, W. B.; Dunitz, J. D. J. Chem. Soc., Chem. Commun. 1984, 853. Enders, D.; Bachstädter, G.; Kremer, K. A. M.; Marsch, M.; Harms, K.; Boche, G. Angew. Chem., Int. Ed. Engl. 1988, 27, 1522. Williard, P. G.; Liu, Q.-Y. J. Am. Chem. Soc. 1993, 115, 3380. Marsch, M.; Harms, K.; Zschage, O.; Hoppe, D.; Boche, G. Angew. Chem., Int. Ed. Engl. 1991, 30, 321. Ahlbrecht, H.; Boche, G.; Harms, K.; Marsch, M.; Sommer, H. Chem. Ber. 1990, 123, 1853. Hoppe, I.; Marsch, M.; Harms, K.; Boche, G.; Hoppe, D. Angew. Chem., Int. Ed. Engl. 1996, 34, 2158. Gawley, R. E.; Zhang, P. J. Org. Chem. 1996, 61, 8103. Hilmersson, G.; Arvidsson, P. I.; Davidsson, Ö.; Håkansson, M. Organometallics 1997, 16, 3352.
41. Attempts to correlate organolithium structure with reaction stereochemistry have been described. Hilmersson, G.; Davidsson, O. J. Organomet. Chem. 1995, 489, 175. Boche, G. Angew. Chem., Int. Ed. Engl. 1989, 28, 277. Hilmersson, G.; Ahlberg, P.; Davidsson, O. J. Am. Chem. Soc. 1996, 118, 3539. Gallagher, D. J.; Kerrick, S. T.; Beak, P. J. Am. Chem. Soc. 1992, 114, 5872. Byrne, L. T.; Engelhardt, L. M.; Jacobsen, G. E.; Leung, W.-P.; Papasergio, R. I.; Raston, C. L.; Skelton, B. W.; Twiss, P.; White, A. H. J. Chem. Soc., Dalton Trans. 1989, 105, Gais, H.-J.; Dingerdissen, U.; Krüger, C.; Angermund, K. J. Am. Chem. Soc. 1987, 109, 3775. Zaegel, F.; Gallucci, J. C.; Meunier, P.; Gautheron, B.; Sivik, M. R.; Paquette, L. A. J. Am. Chem. Soc. 1994, 116, 6466. Cramer, C. J.; Denmark, S. E.; Miller, P. C.; Dorow, R. L.; Swiss, K. A.; Wilson, S. R. J. Am. Chem. Soc. 1994, 116, 2437. Williard, P. G.; Tata, J. R.; Schlessinger, R. H.; Adams, A. D.; Iwanowicz, E. J. J. Am. Chem. Soc. 1988, 110, 7901. Kahne, D.; Gut, S.; DePue, R.; Mohamadi, F.; Wanat, R. A.; Collum, D. B.; Clardy, J.; Van Duyne, G. J. Am. Chem. Soc. 1984, 106, 4685. Wanat, R. A.; Collum, D. B. J. Am. Chem. Soc. 1985, 107, 2078. Galiano-Roth, A. S.; Collum, D. B. J. Am. Chem. Soc. 1988, 110, 3546. Seebach, D.; Bauer, W.; Hansen, J.; Laube, T.; Schweizer, W. B.; Dunitz, J. D. J. Chem. Soc., Chem. Commun. 1984, 853. Enders, D.; Bachstädter, G.; Kremer, K. A. M.; Marsch, M.; Harms, K.; Boche, G. Angew. Chem., Int. Ed. Engl. 1988, 27, 1522. Williard, P. G.; Liu, Q.-Y. J. Am. Chem. Soc. 1993, 115, 3380. Marsch, M.; Harms, K.; Zschage, O.; Hoppe, D.; Boche, G. Angew. Chem., Int. Ed. Engl. 1991, 30, 321. Ahlbrecht, H.; Boche, G.; Harms, K.; Marsch, M.; Sommer, H. Chem. Ber. 1990, 123, 1853. Hoppe, I.; Marsch, M.; Harms, K.; Boche, G.; Hoppe, D. Angew. Chem., Int. Ed. Engl. 1996, 34, 2158. Gawley, R. E.; Zhang, P. J. Org. Chem. 1996, 61, 8103. Hilmersson, G.; Arvidsson, P. I.; Davidsson, Ö.; Håkansson, M. Organometallics 1997, 16, 3352.
42. Attempts to correlate organolithium structure with reaction stereochemistry have been described. Hilmersson, G.; Davidsson, O. J. Organomet. Chem. 1995, 489, 175. Boche, G. Angew. Chem., Int. Ed. Engl. 1989, 28, 277. Hilmersson, G.; Ahlberg, P.; Davidsson, O. J. Am. Chem. Soc. 1996, 118, 3539. Gallagher, D. J.; Kerrick, S. T.; Beak, P. J. Am. Chem. Soc. 1992, 114, 5872. Byrne, L. T.; Engelhardt, L. M.; Jacobsen, G. E.; Leung, W.-P.; Papasergio, R. I.; Raston, C. L.; Skelton, B. W.; Twiss, P.; White, A. H. J. Chem. Soc., Dalton Trans. 1989, 105, Gais, H.-J.; Dingerdissen, U.; Krüger, C.; Angermund, K. J. Am. Chem. Soc. 1987, 109, 3775. Zaegel, F.; Gallucci, J. C.; Meunier, P.; Gautheron, B.; Sivik, M. R.; Paquette, L. A. J. Am. Chem. Soc. 1994, 116, 6466. Cramer, C. J.; Denmark, S. E.; Miller, P. C.; Dorow, R. L.; Swiss, K. A.; Wilson, S. R. J. Am. Chem. Soc. 1994, 116, 2437. Williard, P. G.; Tata, J. R.; Schlessinger, R. H.; Adams, A. D.; Iwanowicz, E. J. J. Am. Chem. Soc. 1988, 110, 7901. Kahne, D.; Gut, S.; DePue, R.; Mohamadi, F.; Wanat, R. A.; Collum, D. B.; Clardy, J.; Van Duyne, G. J. Am. Chem. Soc. 1984, 106, 4685. Wanat, R. A.; Collum, D. B. J. Am. Chem. Soc. 1985, 107, 2078. Galiano-Roth, A. S.; Collum, D. B. J. Am. Chem. Soc. 1988, 110, 3546. Seebach, D.; Bauer, W.; Hansen, J.; Laube, T.; Schweizer, W. B.; Dunitz, J. D. J. Chem. Soc., Chem. Commun. 1984, 853. Enders, D.; Bachstädter, G.; Kremer, K. A. M.; Marsch, M.; Harms, K.; Boche, G. Angew. Chem., Int. Ed. Engl. 1988, 27, 1522. Williard, P. G.; Liu, Q.-Y. J. Am. Chem. Soc. 1993, 115, 3380. Marsch, M.; Harms, K.; Zschage, O.; Hoppe, D.; Boche, G. Angew. Chem., Int. Ed. Engl. 1991, 30, 321. Ahlbrecht, H.; Boche, G.; Harms, K.; Marsch, M.; Sommer, H. Chem. Ber. 1990, 123, 1853. Hoppe, I.; Marsch, M.; Harms, K.; Boche, G.; Hoppe, D. Angew. Chem., Int. Ed. Engl. 1996, 34, 2158. Gawley, R. E.; Zhang, P. J. Org. Chem. 1996, 61, 8103. Hilmersson, G.; Arvidsson, P. I.; Davidsson, Ö.; Håkansson, M. Organometallics 1997, 16, 3352.
43. Attempts to correlate organolithium structure with reaction stereochemistry have been described. Hilmersson, G.; Davidsson, O. J. Organomet. Chem. 1995, 489, 175. Boche, G. Angew. Chem., Int. Ed. Engl. 1989, 28, 277. Hilmersson, G.; Ahlberg, P.; Davidsson, O. J. Am. Chem. Soc. 1996, 118, 3539. Gallagher, D. J.; Kerrick, S. T.; Beak, P. J. Am. Chem. Soc. 1992, 114, 5872. Byrne, L. T.; Engelhardt, L. M.; Jacobsen, G. E.; Leung, W.-P.; Papasergio, R. I.; Raston, C. L.; Skelton, B. W.; Twiss, P.; White, A. H. J. Chem. Soc., Dalton Trans. 1989, 105, Gais, H.-J.; Dingerdissen, U.; Krüger, C.; Angermund, K. J. Am. Chem. Soc. 1987, 109, 3775. Zaegel, F.; Gallucci, J. C.; Meunier, P.; Gautheron, B.; Sivik, M. R.; Paquette, L. A. J. Am. Chem. Soc. 1994, 116, 6466. Cramer, C. J.; Denmark, S. E.; Miller, P. C.; Dorow, R. L.; Swiss, K. A.; Wilson, S. R. J. Am. Chem. Soc. 1994, 116, 2437. Williard, P. G.; Tata, J. R.; Schlessinger, R. H.; Adams, A. D.; Iwanowicz, E. J. J. Am. Chem. Soc. 1988, 110, 7901. Kahne, D.; Gut, S.; DePue, R.; Mohamadi, F.; Wanat, R. A.; Collum, D. B.; Clardy, J.; Van Duyne, G. J. Am. Chem. Soc. 1984, 106, 4685. Wanat, R. A.; Collum, D. B. J. Am. Chem. Soc. 1985, 107, 2078. Galiano-Roth, A. S.; Collum, D. B. J. Am. Chem. Soc. 1988, 110, 3546. Seebach, D.; Bauer, W.; Hansen, J.; Laube, T.; Schweizer, W. B.; Dunitz, J. D. J. Chem. Soc., Chem. Commun. 1984, 853. Enders, D.; Bachstädter, G.; Kremer, K. A. M.; Marsch, M.; Harms, K.; Boche, G. Angew. Chem., Int. Ed. Engl. 1988, 27, 1522. Williard, P. G.; Liu, Q.-Y. J. Am. Chem. Soc. 1993, 115, 3380. Marsch, M.; Harms, K.; Zschage, O.; Hoppe, D.; Boche, G. Angew. Chem., Int. Ed. Engl. 1991, 30, 321. Ahlbrecht, H.; Boche, G.; Harms, K.; Marsch, M.; Sommer, H. Chem. Ber. 1990, 123, 1853. Hoppe, I.; Marsch, M.; Harms, K.; Boche, G.; Hoppe, D. Angew. Chem., Int. Ed. Engl. 1996, 34, 2158. Gawley, R. E.; Zhang, P. J. Org. Chem. 1996, 61, 8103. Hilmersson, G.; Arvidsson, P. I.; Davidsson, Ö.; Håkansson, M. Organometallics 1997, 16, 3352.
44. Attempts to correlate organolithium structure with reaction stereochemistry have been described. Hilmersson, G.; Davidsson, O. J. Organomet. Chem. 1995, 489, 175. Boche, G. Angew. Chem., Int. Ed. Engl. 1989, 28, 277. Hilmersson, G.; Ahlberg, P.; Davidsson, O. J. Am. Chem. Soc. 1996, 118, 3539. Gallagher, D. J.; Kerrick, S. T.; Beak, P. J. Am. Chem. Soc. 1992, 114, 5872. Byrne, L. T.; Engelhardt, L. M.; Jacobsen, G. E.; Leung, W.-P.; Papasergio, R. I.; Raston, C. L.; Skelton, B. W.; Twiss, P.; White, A. H. J. Chem. Soc., Dalton Trans. 1989, 105, Gais, H.-J.; Dingerdissen, U.; Krüger, C.; Angermund, K. J. Am. Chem. Soc. 1987, 109, 3775. Zaegel, F.; Gallucci, J. C.; Meunier, P.; Gautheron, B.; Sivik, M. R.; Paquette, L. A. J. Am. Chem. Soc. 1994, 116, 6466. Cramer, C. J.; Denmark, S. E.; Miller, P. C.; Dorow, R. L.; Swiss, K. A.; Wilson, S. R. J. Am. Chem. Soc. 1994, 116, 2437. Williard, P. G.; Tata, J. R.; Schlessinger, R. H.; Adams, A. D.; Iwanowicz, E. J. J. Am. Chem. Soc. 1988, 110, 7901. Kahne, D.; Gut, S.; DePue, R.; Mohamadi, F.; Wanat, R. A.; Collum, D. B.; Clardy, J.; Van Duyne, G. J. Am. Chem. Soc. 1984, 106, 4685. Wanat, R. A.; Collum, D. B. J. Am. Chem. Soc. 1985, 107, 2078. Galiano-Roth, A. S.; Collum, D. B. J. Am. Chem. Soc. 1988, 110, 3546. Seebach, D.; Bauer, W.; Hansen, J.; Laube, T.; Schweizer, W. B.; Dunitz, J. D. J. Chem. Soc., Chem. Commun. 1984, 853. Enders, D.; Bachstädter, G.; Kremer, K. A. M.; Marsch, M.; Harms, K.; Boche, G. Angew. Chem., Int. Ed. Engl. 1988, 27, 1522. Williard, P. G.; Liu, Q.-Y. J. Am. Chem. Soc. 1993, 115, 3380. Marsch, M.; Harms, K.; Zschage, O.; Hoppe, D.; Boche, G. Angew. Chem., Int. Ed. Engl. 1991, 30, 321. Ahlbrecht, H.; Boche, G.; Harms, K.; Marsch, M.; Sommer, H. Chem. Ber. 1990, 123, 1853. Hoppe, I.; Marsch, M.; Harms, K.; Boche, G.; Hoppe, D. Angew. Chem., Int. Ed. Engl. 1996, 34, 2158. Gawley, R. E.; Zhang, P. J. Org. Chem. 1996, 61, 8103. Hilmersson, G.; Arvidsson, P. I.; Davidsson, Ö.; Håkansson, M. Organometallics 1997, 16, 3352.
45. Attempts to correlate organolithium structure with reaction stereochemistry have been described. Hilmersson, G.; Davidsson, O. J. Organomet. Chem. 1995, 489, 175. Boche, G. Angew. Chem., Int. Ed. Engl. 1989, 28, 277. Hilmersson, G.; Ahlberg, P.; Davidsson, O. J. Am. Chem. Soc. 1996, 118, 3539. Gallagher, D. J.; Kerrick, S. T.; Beak, P. J. Am. Chem. Soc. 1992, 114, 5872. Byrne, L. T.; Engelhardt, L. M.; Jacobsen, G. E.; Leung, W.-P.; Papasergio, R. I.; Raston, C. L.; Skelton, B. W.; Twiss, P.; White, A. H. J. Chem. Soc., Dalton Trans. 1989, 105, Gais, H.-J.; Dingerdissen, U.; Krüger, C.; Angermund, K. J. Am. Chem. Soc. 1987, 109, 3775. Zaegel, F.; Gallucci, J. C.; Meunier, P.; Gautheron, B.; Sivik, M. R.; Paquette, L. A. J. Am. Chem. Soc. 1994, 116, 6466. Cramer, C. J.; Denmark, S. E.; Miller, P. C.; Dorow, R. L.; Swiss, K. A.; Wilson, S. R. J. Am. Chem. Soc. 1994, 116, 2437. Williard, P. G.; Tata, J. R.; Schlessinger, R. H.; Adams, A. D.; Iwanowicz, E. J. J. Am. Chem. Soc. 1988, 110, 7901. Kahne, D.; Gut, S.; DePue, R.; Mohamadi, F.; Wanat, R. A.; Collum, D. B.; Clardy, J.; Van Duyne, G. J. Am. Chem. Soc. 1984, 106, 4685. Wanat, R. A.; Collum, D. B. J. Am. Chem. Soc. 1985, 107, 2078. Galiano-Roth, A. S.; Collum, D. B. J. Am. Chem. Soc. 1988, 110, 3546. Seebach, D.; Bauer, W.; Hansen, J.; Laube, T.; Schweizer, W. B.; Dunitz, J. D. J. Chem. Soc., Chem. Commun. 1984, 853. Enders, D.; Bachstädter, G.; Kremer, K. A. M.; Marsch, M.; Harms, K.; Boche, G. Angew. Chem., Int. Ed. Engl. 1988, 27, 1522. Williard, P. G.; Liu, Q.-Y. J. Am. Chem. Soc. 1993, 115, 3380. Marsch, M.; Harms, K.; Zschage, O.; Hoppe, D.; Boche, G. Angew. Chem., Int. Ed. Engl. 1991, 30, 321. Ahlbrecht, H.; Boche, G.; Harms, K.; Marsch, M.; Sommer, H. Chem. Ber. 1990, 123, 1853. Hoppe, I.; Marsch, M.; Harms, K.; Boche, G.; Hoppe, D. Angew. Chem., Int. Ed. Engl. 1996, 34, 2158. Gawley, R. E.; Zhang, P. J. Org. Chem. 1996, 61, 8103. Hilmersson, G.; Arvidsson, P. I.; Davidsson, Ö.; Håkansson, M. Organometallics 1997, 16, 3352.
46. Attempts to correlate organolithium structure with reaction stereochemistry have been described. Hilmersson, G.; Davidsson, O. J. Organomet. Chem. 1995, 489, 175. Boche, G. Angew. Chem., Int. Ed. Engl. 1989, 28, 277. Hilmersson, G.; Ahlberg, P.; Davidsson, O. J. Am. Chem. Soc. 1996, 118, 3539. Gallagher, D. J.; Kerrick, S. T.; Beak, P. J. Am. Chem. Soc. 1992, 114, 5872. Byrne, L. T.; Engelhardt, L. M.; Jacobsen, G. E.; Leung, W.-P.; Papasergio, R. I.; Raston, C. L.; Skelton, B. W.; Twiss, P.; White, A. H. J. Chem. Soc., Dalton Trans. 1989, 105, Gais, H.-J.; Dingerdissen, U.; Krüger, C.; Angermund, K. J. Am. Chem. Soc. 1987, 109, 3775. Zaegel, F.; Gallucci, J. C.; Meunier, P.; Gautheron, B.; Sivik, M. R.; Paquette, L. A. J. Am. Chem. Soc. 1994, 116, 6466. Cramer, C. J.; Denmark, S. E.; Miller, P. C.; Dorow, R. L.; Swiss, K. A.; Wilson, S. R. J. Am. Chem. Soc. 1994, 116, 2437. Williard, P. G.; Tata, J. R.; Schlessinger, R. H.; Adams, A. D.; Iwanowicz, E. J. J. Am. Chem. Soc. 1988, 110, 7901. Kahne, D.; Gut, S.; DePue, R.; Mohamadi, F.; Wanat, R. A.; Collum, D. B.; Clardy, J.; Van Duyne, G. J. Am. Chem. Soc. 1984, 106, 4685. Wanat, R. A.; Collum, D. B. J. Am. Chem. Soc. 1985, 107, 2078. Galiano-Roth, A. S.; Collum, D. B. J. Am. Chem. Soc. 1988, 110, 3546. Seebach, D.; Bauer, W.; Hansen, J.; Laube, T.; Schweizer, W. B.; Dunitz, J. D. J. Chem. Soc., Chem. Commun. 1984, 853. Enders, D.; Bachstädter, G.; Kremer, K. A. M.; Marsch, M.; Harms, K.; Boche, G. Angew. Chem., Int. Ed. Engl. 1988, 27, 1522. Williard, P. G.; Liu, Q.-Y. J. Am. Chem. Soc. 1993, 115, 3380. Marsch, M.; Harms, K.; Zschage, O.; Hoppe, D.; Boche, G. Angew. Chem., Int. Ed. Engl. 1991, 30, 321. Ahlbrecht, H.; Boche, G.; Harms, K.; Marsch, M.; Sommer, H. Chem. Ber. 1990, 123, 1853. Hoppe, I.; Marsch, M.; Harms, K.; Boche, G.; Hoppe, D. Angew. Chem., Int. Ed. Engl. 1996, 34, 2158. Gawley, R. E.; Zhang, P. J. Org. Chem. 1996, 61, 8103. Hilmersson, G.; Arvidsson, P. I.; Davidsson, Ö.; Håkansson, M. Organometallics 1997, 16, 3352.
47. Attempts to correlate organolithium structure with reaction stereochemistry have been described. Hilmersson, G.; Davidsson, O. J. Organomet. Chem. 1995, 489, 175. Boche, G. Angew. Chem., Int. Ed. Engl. 1989, 28, 277. Hilmersson, G.; Ahlberg, P.; Davidsson, O. J. Am. Chem. Soc. 1996, 118, 3539. Gallagher, D. J.; Kerrick, S. T.; Beak, P. J. Am. Chem. Soc. 1992, 114, 5872. Byrne, L. T.; Engelhardt, L. M.; Jacobsen, G. E.; Leung, W.-P.; Papasergio, R. I.; Raston, C. L.; Skelton, B. W.; Twiss, P.; White, A. H. J. Chem. Soc., Dalton Trans. 1989, 105, Gais, H.-J.; Dingerdissen, U.; Krüger, C.; Angermund, K. J. Am. Chem. Soc. 1987, 109, 3775. Zaegel, F.; Gallucci, J. C.; Meunier, P.; Gautheron, B.; Sivik, M. R.; Paquette, L. A. J. Am. Chem. Soc. 1994, 116, 6466. Cramer, C. J.; Denmark, S. E.; Miller, P. C.; Dorow, R. L.; Swiss, K. A.; Wilson, S. R. J. Am. Chem. Soc. 1994, 116, 2437. Williard, P. G.; Tata, J. R.; Schlessinger, R. H.; Adams, A. D.; Iwanowicz, E. J. J. Am. Chem. Soc. 1988, 110, 7901. Kahne, D.; Gut, S.; DePue, R.; Mohamadi, F.; Wanat, R. A.; Collum, D. B.; Clardy, J.; Van Duyne, G. J. Am. Chem. Soc. 1984, 106, 4685. Wanat, R. A.; Collum, D. B. J. Am. Chem. Soc. 1985, 107, 2078. Galiano-Roth, A. S.; Collum, D. B. J. Am. Chem. Soc. 1988, 110, 3546. Seebach, D.; Bauer, W.; Hansen, J.; Laube, T.; Schweizer, W. B.; Dunitz, J. D. J. Chem. Soc., Chem. Commun. 1984, 853. Enders, D.; Bachstädter, G.; Kremer, K. A. M.; Marsch, M.; Harms, K.; Boche, G. Angew. Chem., Int. Ed. Engl. 1988, 27, 1522. Williard, P. G.; Liu, Q.-Y. J. Am. Chem. Soc. 1993, 115, 3380. Marsch, M.; Harms, K.; Zschage, O.; Hoppe, D.; Boche, G. Angew. Chem., Int. Ed. Engl. 1991, 30, 321. Ahlbrecht, H.; Boche, G.; Harms, K.; Marsch, M.; Sommer, H. Chem. Ber. 1990, 123, 1853. Hoppe, I.; Marsch, M.; Harms, K.; Boche, G.; Hoppe, D. Angew. Chem., Int. Ed. Engl. 1996, 34, 2158. Gawley, R. E.; Zhang, P. J. Org. Chem. 1996, 61, 8103. Hilmersson, G.; Arvidsson, P. I.; Davidsson, Ö.; Håkansson, M. Organometallics 1997, 16, 3352.
48. Attempts to correlate organolithium structure with reaction stereochemistry have been described. Hilmersson, G.; Davidsson, O. J. Organomet. Chem. 1995, 489, 175. Boche, G. Angew. Chem., Int. Ed. Engl. 1989, 28, 277. Hilmersson, G.; Ahlberg, P.; Davidsson, O. J. Am. Chem. Soc. 1996, 118, 3539. Gallagher, D. J.; Kerrick, S. T.; Beak, P. J. Am. Chem. Soc. 1992, 114, 5872. Byrne, L. T.; Engelhardt, L. M.; Jacobsen, G. E.; Leung, W.-P.; Papasergio, R. I.; Raston, C. L.; Skelton, B. W.; Twiss, P.; White, A. H. J. Chem. Soc., Dalton Trans. 1989, 105, Gais, H.-J.; Dingerdissen, U.; Krüger, C.; Angermund, K. J. Am. Chem. Soc. 1987, 109, 3775. Zaegel, F.; Gallucci, J. C.; Meunier, P.; Gautheron, B.; Sivik, M. R.; Paquette, L. A. J. Am. Chem. Soc. 1994, 116, 6466. Cramer, C. J.; Denmark, S. E.; Miller, P. C.; Dorow, R. L.; Swiss, K. A.; Wilson, S. R. J. Am. Chem. Soc. 1994, 116, 2437. Williard, P. G.; Tata, J. R.; Schlessinger, R. H.; Adams, A. D.; Iwanowicz, E. J. J. Am. Chem. Soc. 1988, 110, 7901. Kahne, D.; Gut, S.; DePue, R.; Mohamadi, F.; Wanat, R. A.; Collum, D. B.; Clardy, J.; Van Duyne, G. J. Am. Chem. Soc. 1984, 106, 4685. Wanat, R. A.; Collum, D. B. J. Am. Chem. Soc. 1985, 107, 2078. Galiano-Roth, A. S.; Collum, D. B. J. Am. Chem. Soc. 1988, 110, 3546. Seebach, D.; Bauer, W.; Hansen, J.; Laube, T.; Schweizer, W. B.; Dunitz, J. D. J. Chem. Soc., Chem. Commun. 1984, 853. Enders, D.; Bachstädter, G.; Kremer, K. A. M.; Marsch, M.; Harms, K.; Boche, G. Angew. Chem., Int. Ed. Engl. 1988, 27, 1522. Williard, P. G.; Liu, Q.-Y. J. Am. Chem. Soc. 1993, 115, 3380. Marsch, M.; Harms, K.; Zschage, O.; Hoppe, D.; Boche, G. Angew. Chem., Int. Ed. Engl. 1991, 30, 321. Ahlbrecht, H.; Boche, G.; Harms, K.; Marsch, M.; Sommer, H. Chem. Ber. 1990, 123, 1853. Hoppe, I.; Marsch, M.; Harms, K.; Boche, G.; Hoppe, D. Angew. Chem., Int. Ed. Engl. 1996, 34, 2158. Gawley, R. E.; Zhang, P. J. Org. Chem. 1996, 61, 8103. Hilmersson, G.; Arvidsson, P. I.; Davidsson, Ö.; Håkansson, M. Organometallics 1997, 16, 3352.
49. Attempts to correlate organolithium structure with reaction stereochemistry have been described. Hilmersson, G.; Davidsson, O. J. Organomet. Chem. 1995, 489, 175. Boche, G. Angew. Chem., Int. Ed. Engl. 1989, 28, 277. Hilmersson, G.; Ahlberg, P.; Davidsson, O. J. Am. Chem. Soc. 1996, 118, 3539. Gallagher, D. J.; Kerrick, S. T.; Beak, P. J. Am. Chem. Soc. 1992, 114, 5872. Byrne, L. T.; Engelhardt, L. M.; Jacobsen, G. E.; Leung, W.-P.; Papasergio, R. I.; Raston, C. L.; Skelton, B. W.; Twiss, P.; White, A. H. J. Chem. Soc., Dalton Trans. 1989, 105, Gais, H.-J.; Dingerdissen, U.; Krüger, C.; Angermund, K. J. Am. Chem. Soc. 1987, 109, 3775. Zaegel, F.; Gallucci, J. C.; Meunier, P.; Gautheron, B.; Sivik, M. R.; Paquette, L. A. J. Am. Chem. Soc. 1994, 116, 6466. Cramer, C. J.; Denmark, S. E.; Miller, P. C.; Dorow, R. L.; Swiss, K. A.; Wilson, S. R. J. Am. Chem. Soc. 1994, 116, 2437. Williard, P. G.; Tata, J. R.; Schlessinger, R. H.; Adams, A. D.; Iwanowicz, E. J. J. Am. Chem. Soc. 1988, 110, 7901. Kahne, D.; Gut, S.; DePue, R.; Mohamadi, F.; Wanat, R. A.; Collum, D. B.; Clardy, J.; Van Duyne, G. J. Am. Chem. Soc. 1984, 106, 4685. Wanat, R. A.; Collum, D. B. J. Am. Chem. Soc. 1985, 107, 2078. Galiano-Roth, A. S.; Collum, D. B. J. Am. Chem. Soc. 1988, 110, 3546. Seebach, D.; Bauer, W.; Hansen, J.; Laube, T.; Schweizer, W. B.; Dunitz, J. D. J. Chem. Soc., Chem. Commun. 1984, 853. Enders, D.; Bachstädter, G.; Kremer, K. A. M.; Marsch, M.; Harms, K.; Boche, G. Angew. Chem., Int. Ed. Engl. 1988, 27, 1522. Williard, P. G.; Liu, Q.-Y. J. Am. Chem. Soc. 1993, 115, 3380. Marsch, M.; Harms, K.; Zschage, O.; Hoppe, D.; Boche, G. Angew. Chem., Int. Ed. Engl. 1991, 30, 321. Ahlbrecht, H.; Boche, G.; Harms, K.; Marsch, M.; Sommer, H. Chem. Ber. 1990, 123, 1853. Hoppe, I.; Marsch, M.; Harms, K.; Boche, G.; Hoppe, D. Angew. Chem., Int. Ed. Engl. 1996, 34, 2158. Gawley, R. E.; Zhang, P. J. Org. Chem. 1996, 61, 8103. Hilmersson, G.; Arvidsson, P. I.; Davidsson, Ö.; Håkansson, M. Organometallics 1997, 16, 3352.
50. Attempts to correlate organolithium structure with reaction stereochemistry have been described. Hilmersson, G.; Davidsson, O. J. Organomet. Chem. 1995, 489, 175. Boche, G. Angew. Chem., Int. Ed. Engl. 1989, 28, 277. Hilmersson, G.; Ahlberg, P.; Davidsson, O. J. Am. Chem. Soc. 1996, 118, 3539. Gallagher, D. J.; Kerrick, S. T.; Beak, P. J. Am. Chem. Soc. 1992, 114, 5872. Byrne, L. T.; Engelhardt, L. M.; Jacobsen, G. E.; Leung, W.-P.; Papasergio, R. I.; Raston, C. L.; Skelton, B. W.; Twiss, P.; White, A. H. J. Chem. Soc., Dalton Trans. 1989, 105, Gais, H.-J.; Dingerdissen, U.; Krüger, C.; Angermund, K. J. Am. Chem. Soc. 1987, 109, 3775. Zaegel, F.; Gallucci, J. C.; Meunier, P.; Gautheron, B.; Sivik, M. R.; Paquette, L. A. J. Am. Chem. Soc. 1994, 116, 6466. Cramer, C. J.; Denmark, S. E.; Miller, P. C.; Dorow, R. L.; Swiss, K. A.; Wilson, S. R. J. Am. Chem. Soc. 1994, 116, 2437. Williard, P. G.; Tata, J. R.; Schlessinger, R. H.; Adams, A. D.; Iwanowicz, E. J. J. Am. Chem. Soc. 1988, 110, 7901. Kahne, D.; Gut, S.; DePue, R.; Mohamadi, F.; Wanat, R. A.; Collum, D. B.; Clardy, J.; Van Duyne, G. J. Am. Chem. Soc. 1984, 106, 4685. Wanat, R. A.; Collum, D. B. J. Am. Chem. Soc. 1985, 107, 2078. Galiano-Roth, A. S.; Collum, D. B. J. Am. Chem. Soc. 1988, 110, 3546. Seebach, D.; Bauer, W.; Hansen, J.; Laube, T.; Schweizer, W. B.; Dunitz, J. D. J. Chem. Soc., Chem. Commun. 1984, 853. Enders, D.; Bachstädter, G.; Kremer, K. A. M.; Marsch, M.; Harms, K.; Boche, G. Angew. Chem., Int. Ed. Engl. 1988, 27, 1522. Williard, P. G.; Liu, Q.-Y. J. Am. Chem. Soc. 1993, 115, 3380. Marsch, M.; Harms, K.; Zschage, O.; Hoppe, D.; Boche, G. Angew. Chem., Int. Ed. Engl. 1991, 30, 321. Ahlbrecht, H.; Boche, G.; Harms, K.; Marsch, M.; Sommer, H. Chem. Ber. 1990, 123, 1853. Hoppe, I.; Marsch, M.; Harms, K.; Boche, G.; Hoppe, D. Angew. Chem., Int. Ed. Engl. 1996, 34, 2158. Gawley, R. E.; Zhang, P. J. Org. Chem. 1996, 61, 8103. Hilmersson, G.; Arvidsson, P. I.; Davidsson, Ö.; Håkansson, M. Organometallics 1997, 16, 3352.
51. Attempts to correlate organolithium structure with reaction stereochemistry have been described. Hilmersson, G.; Davidsson, O. J. Organomet. Chem. 1995, 489, 175. Boche, G. Angew. Chem., Int. Ed. Engl. 1989, 28, 277. Hilmersson, G.; Ahlberg, P.; Davidsson, O. J. Am. Chem. Soc. 1996, 118, 3539. Gallagher, D. J.; Kerrick, S. T.; Beak, P. J. Am. Chem. Soc. 1992, 114, 5872. Byrne, L. T.; Engelhardt, L. M.; Jacobsen, G. E.; Leung, W.-P.; Papasergio, R. I.; Raston, C. L.; Skelton, B. W.; Twiss, P.; White, A. H. J. Chem. Soc., Dalton Trans. 1989, 105, Gais, H.-J.; Dingerdissen, U.; Krüger, C.; Angermund, K. J. Am. Chem. Soc. 1987, 109, 3775. Zaegel, F.; Gallucci, J. C.; Meunier, P.; Gautheron, B.; Sivik, M. R.; Paquette, L. A. J. Am. Chem. Soc. 1994, 116, 6466. Cramer, C. J.; Denmark, S. E.; Miller, P. C.; Dorow, R. L.; Swiss, K. A.; Wilson, S. R. J. Am. Chem. Soc. 1994, 116, 2437. Williard, P. G.; Tata, J. R.; Schlessinger, R. H.; Adams, A. D.; Iwanowicz, E. J. J. Am. Chem. Soc. 1988, 110, 7901. Kahne, D.; Gut, S.; DePue, R.; Mohamadi, F.; Wanat, R. A.; Collum, D. B.; Clardy, J.; Van Duyne, G. J. Am. Chem. Soc. 1984, 106, 4685. Wanat, R. A.; Collum, D. B. J. Am. Chem. Soc. 1985, 107, 2078. Galiano-Roth, A. S.; Collum, D. B. J. Am. Chem. Soc. 1988, 110, 3546. Seebach, D.; Bauer, W.; Hansen, J.; Laube, T.; Schweizer, W. B.; Dunitz, J. D. J. Chem. Soc., Chem. Commun. 1984, 853. Enders, D.; Bachstädter, G.; Kremer, K. A. M.; Marsch, M.; Harms, K.; Boche, G. Angew. Chem., Int. Ed. Engl. 1988, 27, 1522. Williard, P. G.; Liu, Q.-Y. J. Am. Chem. Soc. 1993, 115, 3380. Marsch, M.; Harms, K.; Zschage, O.; Hoppe, D.; Boche, G. Angew. Chem., Int. Ed. Engl. 1991, 30, 321. Ahlbrecht, H.; Boche, G.; Harms, K.; Marsch, M.; Sommer, H. Chem. Ber. 1990, 123, 1853. Hoppe, I.; Marsch, M.; Harms, K.; Boche, G.; Hoppe, D. Angew. Chem., Int. Ed. Engl. 1996, 34, 2158. Gawley, R. E.; Zhang, P. J. Org. Chem. 1996, 61, 8103. Hilmersson, G.; Arvidsson, P. I.; Davidsson, Ö.; Håkansson, M. Organometallics 1997, 16, 3352.
52. Attempts to correlate organolithium structure with reaction stereochemistry have been described. Hilmersson, G.; Davidsson, O. J. Organomet. Chem. 1995, 489, 175. Boche, G. Angew. Chem., Int. Ed. Engl. 1989, 28, 277. Hilmersson, G.; Ahlberg, P.; Davidsson, O. J. Am. Chem. Soc. 1996, 118, 3539. Gallagher, D. J.; Kerrick, S. T.; Beak, P. J. Am. Chem. Soc. 1992, 114, 5872. Byrne, L. T.; Engelhardt, L. M.; Jacobsen, G. E.; Leung, W.-P.; Papasergio, R. I.; Raston, C. L.; Skelton, B. W.; Twiss, P.; White, A. H. J. Chem. Soc., Dalton Trans. 1989, 105, Gais, H.-J.; Dingerdissen, U.; Krüger, C.; Angermund, K. J. Am. Chem. Soc. 1987, 109, 3775. Zaegel, F.; Gallucci, J. C.; Meunier, P.; Gautheron, B.; Sivik, M. R.; Paquette, L. A. J. Am. Chem. Soc. 1994, 116, 6466. Cramer, C. J.; Denmark, S. E.; Miller, P. C.; Dorow, R. L.; Swiss, K. A.; Wilson, S. R. J. Am. Chem. Soc. 1994, 116, 2437. Williard, P. G.; Tata, J. R.; Schlessinger, R. H.; Adams, A. D.; Iwanowicz, E. J. J. Am. Chem. Soc. 1988, 110, 7901. Kahne, D.; Gut, S.; DePue, R.; Mohamadi, F.; Wanat, R. A.; Collum, D. B.; Clardy, J.; Van Duyne, G. J. Am. Chem. Soc. 1984, 106, 4685. Wanat, R. A.; Collum, D. B. J. Am. Chem. Soc. 1985, 107, 2078. Galiano-Roth, A. S.; Collum, D. B. J. Am. Chem. Soc. 1988, 110, 3546. Seebach, D.; Bauer, W.; Hansen, J.; Laube, T.; Schweizer, W. B.; Dunitz, J. D. J. Chem. Soc., Chem. Commun. 1984, 853. Enders, D.; Bachstädter, G.; Kremer, K. A. M.; Marsch, M.; Harms, K.; Boche, G. Angew. Chem., Int. Ed. Engl. 1988, 27, 1522. Williard, P. G.; Liu, Q.-Y. J. Am. Chem. Soc. 1993, 115, 3380. Marsch, M.; Harms, K.; Zschage, O.; Hoppe, D.; Boche, G. Angew. Chem., Int. Ed. Engl. 1991, 30, 321. Ahlbrecht, H.; Boche, G.; Harms, K.; Marsch, M.; Sommer, H. Chem. Ber. 1990, 123, 1853. Hoppe, I.; Marsch, M.; Harms, K.; Boche, G.; Hoppe, D. Angew. Chem., Int. Ed. Engl. 1996, 34, 2158. Gawley, R. E.; Zhang, P. J. Org. Chem. 1996, 61, 8103. Hilmersson, G.; Arvidsson, P. I.; Davidsson, Ö.; Håkansson, M. Organometallics 1997, 16, 3352.
53. Attempts to correlate organolithium structure with reaction stereochemistry have been described. Hilmersson, G.; Davidsson, O. J. Organomet. Chem. 1995, 489, 175. Boche, G. Angew. Chem., Int. Ed. Engl. 1989, 28, 277. Hilmersson, G.; Ahlberg, P.; Davidsson, O. J. Am. Chem. Soc. 1996, 118, 3539. Gallagher, D. J.; Kerrick, S. T.; Beak, P. J. Am. Chem. Soc. 1992, 114, 5872. Byrne, L. T.; Engelhardt, L. M.; Jacobsen, G. E.; Leung, W.-P.; Papasergio, R. I.; Raston, C. L.; Skelton, B. W.; Twiss, P.; White, A. H. J. Chem. Soc., Dalton Trans. 1989, 105, Gais, H.-J.; Dingerdissen, U.; Krüger, C.; Angermund, K. J. Am. Chem. Soc. 1987, 109, 3775. Zaegel, F.; Gallucci, J. C.; Meunier, P.; Gautheron, B.; Sivik, M. R.; Paquette, L. A. J. Am. Chem. Soc. 1994, 116, 6466. Cramer, C. J.; Denmark, S. E.; Miller, P. C.; Dorow, R. L.; Swiss, K. A.; Wilson, S. R. J. Am. Chem. Soc. 1994, 116, 2437. Williard, P. G.; Tata, J. R.; Schlessinger, R. H.; Adams, A. D.; Iwanowicz, E. J. J. Am. Chem. Soc. 1988, 110, 7901. Kahne, D.; Gut, S.; DePue, R.; Mohamadi, F.; Wanat, R. A.; Collum, D. B.; Clardy, J.; Van Duyne, G. J. Am. Chem. Soc. 1984, 106, 4685. Wanat, R. A.; Collum, D. B. J. Am. Chem. Soc. 1985, 107, 2078. Galiano-Roth, A. S.; Collum, D. B. J. Am. Chem. Soc. 1988, 110, 3546. Seebach, D.; Bauer, W.; Hansen, J.; Laube, T.; Schweizer, W. B.; Dunitz, J. D. J. Chem. Soc., Chem. Commun. 1984, 853. Enders, D.; Bachstädter, G.; Kremer, K. A. M.; Marsch, M.; Harms, K.; Boche, G. Angew. Chem., Int. Ed. Engl. 1988, 27, 1522. Williard, P. G.; Liu, Q.-Y. J. Am. Chem. Soc. 1993, 115, 3380. Marsch, M.; Harms, K.; Zschage, O.; Hoppe, D.; Boche, G. Angew. Chem., Int. Ed. Engl. 1991, 30, 321. Ahlbrecht, H.; Boche, G.; Harms, K.; Marsch, M.; Sommer, H. Chem. Ber. 1990, 123, 1853. Hoppe, I.; Marsch, M.; Harms, K.; Boche, G.; Hoppe, D. Angew. Chem., Int. Ed. Engl. 1996, 34, 2158. Gawley, R. E.; Zhang, P. J. Org. Chem. 1996, 61, 8103. Hilmersson, G.; Arvidsson, P. I.; Davidsson, Ö.; Håkansson, M. Organometallics 1997, 16, 3352.
54. Attempts to correlate organolithium structure with reaction stereochemistry have been described. Hilmersson, G.; Davidsson, O. J. Organomet. Chem. 1995, 489, 175. Boche, G. Angew. Chem., Int. Ed. Engl. 1989, 28, 277. Hilmersson, G.; Ahlberg, P.; Davidsson, O. J. Am. Chem. Soc. 1996, 118, 3539. Gallagher, D. J.; Kerrick, S. T.; Beak, P. J. Am. Chem. Soc. 1992, 114, 5872. Byrne, L. T.; Engelhardt, L. M.; Jacobsen, G. E.; Leung, W.-P.; Papasergio, R. I.; Raston, C. L.; Skelton, B. W.; Twiss, P.; White, A. H. J. Chem. Soc., Dalton Trans. 1989, 105, Gais, H.-J.; Dingerdissen, U.; Krüger, C.; Angermund, K. J. Am. Chem. Soc. 1987, 109, 3775. Zaegel, F.; Gallucci, J. C.; Meunier, P.; Gautheron, B.; Sivik, M. R.; Paquette, L. A. J. Am. Chem. Soc. 1994, 116, 6466. Cramer, C. J.; Denmark, S. E.; Miller, P. C.; Dorow, R. L.; Swiss, K. A.; Wilson, S. R. J. Am. Chem. Soc. 1994, 116, 2437. Williard, P. G.; Tata, J. R.; Schlessinger, R. H.; Adams, A. D.; Iwanowicz, E. J. J. Am. Chem. Soc. 1988, 110, 7901. Kahne, D.; Gut, S.; DePue, R.; Mohamadi, F.; Wanat, R. A.; Collum, D. B.; Clardy, J.; Van Duyne, G. J. Am. Chem. Soc. 1984, 106, 4685. Wanat, R. A.; Collum, D. B. J. Am. Chem. Soc. 1985, 107, 2078. Galiano-Roth, A. S.; Collum, D. B. J. Am. Chem. Soc. 1988, 110, 3546. Seebach, D.; Bauer, W.; Hansen, J.; Laube, T.; Schweizer, W. B.; Dunitz, J. D. J. Chem. Soc., Chem. Commun. 1984, 853. Enders, D.; Bachstädter, G.; Kremer, K. A. M.; Marsch, M.; Harms, K.; Boche, G. Angew. Chem., Int. Ed. Engl. 1988, 27, 1522. Williard, P. G.; Liu, Q.-Y. J. Am. Chem. Soc. 1993, 115, 3380. Marsch, M.; Harms, K.; Zschage, O.; Hoppe, D.; Boche, G. Angew. Chem., Int. Ed. Engl. 1991, 30, 321. Ahlbrecht, H.; Boche, G.; Harms, K.; Marsch, M.; Sommer, H. Chem. Ber. 1990, 123, 1853. Hoppe, I.; Marsch, M.; Harms, K.; Boche, G.; Hoppe, D. Angew. Chem., Int. Ed. Engl. 1996, 34, 2158. Gawley, R. E.; Zhang, P. J. Org. Chem. 1996, 61, 8103. Hilmersson, G.; Arvidsson, P. I.; Davidsson, Ö.; Håkansson, M. Organometallics 1997, 16, 3352.
55. Attempts to correlate organolithium structure with reaction stereochemistry have been described. Hilmersson, G.; Davidsson, O. J. Organomet. Chem. 1995, 489, 175. Boche, G. Angew. Chem., Int. Ed. Engl. 1989, 28, 277. Hilmersson, G.; Ahlberg, P.; Davidsson, O. J. Am. Chem. Soc. 1996, 118, 3539. Gallagher, D. J.; Kerrick, S. T.; Beak, P. J. Am. Chem. Soc. 1992, 114, 5872. Byrne, L. T.; Engelhardt, L. M.; Jacobsen, G. E.; Leung, W.-P.; Papasergio, R. I.; Raston, C. L.; Skelton, B. W.; Twiss, P.; White, A. H. J. Chem. Soc., Dalton Trans. 1989, 105, Gais, H.-J.; Dingerdissen, U.; Krüger, C.; Angermund, K. J. Am. Chem. Soc. 1987, 109, 3775. Zaegel, F.; Gallucci, J. C.; Meunier, P.; Gautheron, B.; Sivik, M. R.; Paquette, L. A. J. Am. Chem. Soc. 1994, 116, 6466. Cramer, C. J.; Denmark, S. E.; Miller, P. C.; Dorow, R. L.; Swiss, K. A.; Wilson, S. R. J. Am. Chem. Soc. 1994, 116, 2437. Williard, P. G.; Tata, J. R.; Schlessinger, R. H.; Adams, A. D.; Iwanowicz, E. J. J. Am. Chem. Soc. 1988, 110, 7901. Kahne, D.; Gut, S.; DePue, R.; Mohamadi, F.; Wanat, R. A.; Collum, D. B.; Clardy, J.; Van Duyne, G. J. Am. Chem. Soc. 1984, 106, 4685. Wanat, R. A.; Collum, D. B. J. Am. Chem. Soc. 1985, 107, 2078. Galiano-Roth, A. S.; Collum, D. B. J. Am. Chem. Soc. 1988, 110, 3546. Seebach, D.; Bauer, W.; Hansen, J.; Laube, T.; Schweizer, W. B.; Dunitz, J. D. J. Chem. Soc., Chem. Commun. 1984, 853. Enders, D.; Bachstädter, G.; Kremer, K. A. M.; Marsch, M.; Harms, K.; Boche, G. Angew. Chem., Int. Ed. Engl. 1988, 27, 1522. Williard, P. G.; Liu, Q.-Y. J. Am. Chem. Soc. 1993, 115, 3380. Marsch, M.; Harms, K.; Zschage, O.; Hoppe, D.; Boche, G. Angew. Chem., Int. Ed. Engl. 1991, 30, 321. Ahlbrecht, H.; Boche, G.; Harms, K.; Marsch, M.; Sommer, H. Chem. Ber. 1990, 123, 1853. Hoppe, I.; Marsch, M.; Harms, K.; Boche, G.; Hoppe, D. Angew. Chem., Int. Ed. Engl. 1996, 34, 2158. Gawley, R. E.; Zhang, P. J. Org. Chem. 1996, 61, 8103. Hilmersson, G.; Arvidsson, P. I.; Davidsson, Ö.; Håkansson, M. Organometallics 1997, 16, 3352.
56. Attempts to correlate organolithium structure with reaction stereochemistry have been described. Hilmersson, G.; Davidsson, O. J. Organomet. Chem. 1995, 489, 175. Boche, G. Angew. Chem., Int. Ed. Engl. 1989, 28, 277. Hilmersson, G.; Ahlberg, P.; Davidsson, O. J. Am. Chem. Soc. 1996, 118, 3539. Gallagher, D. J.; Kerrick, S. T.; Beak, P. J. Am. Chem. Soc. 1992, 114, 5872. Byrne, L. T.; Engelhardt, L. M.; Jacobsen, G. E.; Leung, W.-P.; Papasergio, R. I.; Raston, C. L.; Skelton, B. W.; Twiss, P.; White, A. H. J. Chem. Soc., Dalton Trans. 1989, 105, Gais, H.-J.; Dingerdissen, U.; Krüger, C.; Angermund, K. J. Am. Chem. Soc. 1987, 109, 3775. Zaegel, F.; Gallucci, J. C.; Meunier, P.; Gautheron, B.; Sivik, M. R.; Paquette, L. A. J. Am. Chem. Soc. 1994, 116, 6466. Cramer, C. J.; Denmark, S. E.; Miller, P. C.; Dorow, R. L.; Swiss, K. A.; Wilson, S. R. J. Am. Chem. Soc. 1994, 116, 2437. Williard, P. G.; Tata, J. R.; Schlessinger, R. H.; Adams, A. D.; Iwanowicz, E. J. J. Am. Chem. Soc. 1988, 110, 7901. Kahne, D.; Gut, S.; DePue, R.; Mohamadi, F.; Wanat, R. A.; Collum, D. B.; Clardy, J.; Van Duyne, G. J. Am. Chem. Soc. 1984, 106, 4685. Wanat, R. A.; Collum, D. B. J. Am. Chem. Soc. 1985, 107, 2078. Galiano-Roth, A. S.; Collum, D. B. J. Am. Chem. Soc. 1988, 110, 3546. Seebach, D.; Bauer, W.; Hansen, J.; Laube, T.; Schweizer, W. B.; Dunitz, J. D. J. Chem. Soc., Chem. Commun. 1984, 853. Enders, D.; Bachstädter, G.; Kremer, K. A. M.; Marsch, M.; Harms, K.; Boche, G. Angew. Chem., Int. Ed. Engl. 1988, 27, 1522. Williard, P. G.; Liu, Q.-Y. J. Am. Chem. Soc. 1993, 115, 3380. Marsch, M.; Harms, K.; Zschage, O.; Hoppe, D.; Boche, G. Angew. Chem., Int. Ed. Engl. 1991, 30, 321. Ahlbrecht, H.; Boche, G.; Harms, K.; Marsch, M.; Sommer, H. Chem. Ber. 1990, 123, 1853. Hoppe, I.; Marsch, M.; Harms, K.; Boche, G.; Hoppe, D. Angew. Chem., Int. Ed. Engl. 1996, 34, 2158. Gawley, R. E.; Zhang, P. J. Org. Chem. 1996, 61, 8103. Hilmersson, G.; Arvidsson, P. I.; Davidsson, Ö.; Håkansson, M. Organometallics 1997, 16, 3352.
57. Attempts to correlate organolithium structure with reaction stereochemistry have been described. Hilmersson, G.; Davidsson, O. J. Organomet. Chem. 1995, 489, 175. Boche, G. Angew. Chem., Int. Ed. Engl. 1989, 28, 277. Hilmersson, G.; Ahlberg, P.; Davidsson, O. J. Am. Chem. Soc. 1996, 118, 3539. Gallagher, D. J.; Kerrick, S. T.; Beak, P. J. Am. Chem. Soc. 1992, 114, 5872. Byrne, L. T.; Engelhardt, L. M.; Jacobsen, G. E.; Leung, W.-P.; Papasergio, R. I.; Raston, C. L.; Skelton, B. W.; Twiss, P.; White, A. H. J. Chem. Soc., Dalton Trans. 1989, 105, Gais, H.-J.; Dingerdissen, U.; Krüger, C.; Angermund, K. J. Am. Chem. Soc. 1987, 109, 3775. Zaegel, F.; Gallucci, J. C.; Meunier, P.; Gautheron, B.; Sivik, M. R.; Paquette, L. A. J. Am. Chem. Soc. 1994, 116, 6466. Cramer, C. J.; Denmark, S. E.; Miller, P. C.; Dorow, R. L.; Swiss, K. A.; Wilson, S. R. J. Am. Chem. Soc. 1994, 116, 2437. Williard, P. G.; Tata, J. R.; Schlessinger, R. H.; Adams, A. D.; Iwanowicz, E. J. J. Am. Chem. Soc. 1988, 110, 7901. Kahne, D.; Gut, S.; DePue, R.; Mohamadi, F.; Wanat, R. A.; Collum, D. B.; Clardy, J.; Van Duyne, G. J. Am. Chem. Soc. 1984, 106, 4685. Wanat, R. A.; Collum, D. B. J. Am. Chem. Soc. 1985, 107, 2078. Galiano-Roth, A. S.; Collum, D. B. J. Am. Chem. Soc. 1988, 110, 3546. Seebach, D.; Bauer, W.; Hansen, J.; Laube, T.; Schweizer, W. B.; Dunitz, J. D. J. Chem. Soc., Chem. Commun. 1984, 853. Enders, D.; Bachstädter, G.; Kremer, K. A. M.; Marsch, M.; Harms, K.; Boche, G. Angew. Chem., Int. Ed. Engl. 1988, 27, 1522. Williard, P. G.; Liu, Q.-Y. J. Am. Chem. Soc. 1993, 115, 3380. Marsch, M.; Harms, K.; Zschage, O.; Hoppe, D.; Boche, G. Angew. Chem., Int. Ed. Engl. 1991, 30, 321. Ahlbrecht, H.; Boche, G.; Harms, K.; Marsch, M.; Sommer, H. Chem. Ber. 1990, 123, 1853. Hoppe, I.; Marsch, M.; Harms, K.; Boche, G.; Hoppe, D. Angew. Chem., Int. Ed. Engl. 1996, 34, 2158. Gawley, R. E.; Zhang, P. J. Org. Chem. 1996, 61, 8103. Hilmersson, G.; Arvidsson, P. I.; Davidsson, Ö.; Håkansson, M. Organometallics 1997, 16, 3352.
58. Attempts to correlate organolithium structure with reaction stereochemistry have been described. Hilmersson, G.; Davidsson, O. J. Organomet. Chem. 1995, 489, 175. Boche, G. Angew. Chem., Int. Ed. Engl. 1989, 28, 277. Hilmersson, G.; Ahlberg, P.; Davidsson, O. J. Am. Chem. Soc. 1996, 118, 3539. Gallagher, D. J.; Kerrick, S. T.; Beak, P. J. Am. Chem. Soc. 1992, 114, 5872. Byrne, L. T.; Engelhardt, L. M.; Jacobsen, G. E.; Leung, W.-P.; Papasergio, R. I.; Raston, C. L.; Skelton, B. W.; Twiss, P.; White, A. H. J. Chem. Soc., Dalton Trans. 1989, 105, Gais, H.-J.; Dingerdissen, U.; Krüger, C.; Angermund, K. J. Am. Chem. Soc. 1987, 109, 3775. Zaegel, F.; Gallucci, J. C.; Meunier, P.; Gautheron, B.; Sivik, M. R.; Paquette, L. A. J. Am. Chem. Soc. 1994, 116, 6466. Cramer, C. J.; Denmark, S. E.; Miller, P. C.; Dorow, R. L.; Swiss, K. A.; Wilson, S. R. J. Am. Chem. Soc. 1994, 116, 2437. Williard, P. G.; Tata, J. R.; Schlessinger, R. H.; Adams, A. D.; Iwanowicz, E. J. J. Am. Chem. Soc. 1988, 110, 7901. Kahne, D.; Gut, S.; DePue, R.; Mohamadi, F.; Wanat, R. A.; Collum, D. B.; Clardy, J.; Van Duyne, G. J. Am. Chem. Soc. 1984, 106, 4685. Wanat, R. A.; Collum, D. B. J. Am. Chem. Soc. 1985, 107, 2078. Galiano-Roth, A. S.; Collum, D. B. J. Am. Chem. Soc. 1988, 110, 3546. Seebach, D.; Bauer, W.; Hansen, J.; Laube, T.; Schweizer, W. B.; Dunitz, J. D. J. Chem. Soc., Chem. Commun. 1984, 853. Enders, D.; Bachstädter, G.; Kremer, K. A. M.; Marsch, M.; Harms, K.; Boche, G. Angew. Chem., Int. Ed. Engl. 1988, 27, 1522. Williard, P. G.; Liu, Q.-Y. J. Am. Chem. Soc. 1993, 115, 3380. Marsch, M.; Harms, K.; Zschage, O.; Hoppe, D.; Boche, G. Angew. Chem., Int. Ed. Engl. 1991, 30, 321. Ahlbrecht, H.; Boche, G.; Harms, K.; Marsch, M.; Sommer, H. Chem. Ber. 1990, 123, 1853. Hoppe, I.; Marsch, M.; Harms, K.; Boche, G.; Hoppe, D. Angew. Chem., Int. Ed. Engl. 1996, 34, 2158. Gawley, R. E.; Zhang, P. J. Org. Chem. 1996, 61, 8103. Hilmersson, G.; Arvidsson, P. I.; Davidsson, Ö.; Håkansson, M. Organometallics 1997, 16, 3352.
59. For other applications of lithium ephedrates, see ref 22.
60. Ruck, K. Angew. Chem., Int. Ed. Engl. 1995, 34, 433. Vadecard, J.; Plaquevent, J.-C.; Duhamel, L.; Duhamel, P. J. Org. Chem. 1994, 59, 2285. Malmvik, A. C.; Obenius, U.; Henriksson, U. J. Chem. Soc., Perkin Trans. 2 1986, 1899. Boireau, G.; Abenhaim, D.; Henry-Basch, E. Tetrahedron 1979, 35, 1457. Gerlach, U.; Haubenreich, T.; Huenig, S. Chem. Ber. 1994, 127, 1969. Kumamoto, T.; Aoki, S.; Nakajima, M.; Koga, K. Tetrahedron: Asymmetry 1994, 5, 1431. Coote, S. J.; Davies, S. G.; Goodfellow, C. L.; Sutton, K. H.; Middlemiss, D.; Naylor, A. Tetrahedron: Asymmetry 1990, 1, 817. Kawasaki, M.; Terashima, S. Chem. Pharm. Bull. 1985, 33, 347. Fehr, C.; Stempf, I.; Galindo, J. Angew. Chem., Int. Ed. Engl. 1993, 32, 1042. Milne, D.; Murphy, P. J. J. Chem. Soc., Chem. Commun. 1993, 884.
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64. Ruck, K. Angew. Chem., Int. Ed. Engl. 1995, 34, 433. Vadecard, J.; Plaquevent, J.-C.; Duhamel, L.; Duhamel, P. J. Org. Chem. 1994, 59, 2285. Malmvik, A. C.; Obenius, U.; Henriksson, U. J. Chem. Soc., Perkin Trans. 2 1986, 1899. Boireau, G.; Abenhaim, D.; Henry-Basch, E. Tetrahedron 1979, 35, 1457. Gerlach, U.; Haubenreich, T.; Huenig, S. Chem. Ber. 1994, 127, 1969. Kumamoto, T.; Aoki, S.; Nakajima, M.; Koga, K. Tetrahedron: Asymmetry 1994, 5, 1431. Coote, S. J.; Davies, S. G.; Goodfellow, C. L.; Sutton, K. H.; Middlemiss, D.; Naylor, A. Tetrahedron: Asymmetry 1990, 1, 817. Kawasaki, M.; Terashima, S. Chem. Pharm. Bull. 1985, 33, 347. Fehr, C.; Stempf, I.; Galindo, J. Angew. Chem., Int. Ed. Engl. 1993, 32, 1042. Milne, D.; Murphy, P. J. J. Chem. Soc., Chem. Commun. 1993, 884.
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66. Ruck, K. Angew. Chem., Int. Ed. Engl. 1995, 34, 433. Vadecard, J.; Plaquevent, J.-C.; Duhamel, L.; Duhamel, P. J. Org. Chem. 1994, 59, 2285. Malmvik, A. C.; Obenius, U.; Henriksson, U. J. Chem. Soc., Perkin Trans. 2 1986, 1899. Boireau, G.; Abenhaim, D.; Henry-Basch, E. Tetrahedron 1979, 35, 1457. Gerlach, U.; Haubenreich, T.; Huenig, S. Chem. Ber. 1994, 127, 1969. Kumamoto, T.; Aoki, S.; Nakajima, M.; Koga, K. Tetrahedron: Asymmetry 1994, 5, 1431. Coote, S. J.; Davies, S. G.; Goodfellow, C. L.; Sutton, K. H.; Middlemiss, D.; Naylor, A. Tetrahedron: Asymmetry 1990, 1, 817. Kawasaki, M.; Terashima, S. Chem. Pharm. Bull. 1985, 33, 347. Fehr, C.; Stempf, I.; Galindo, J. Angew. Chem., Int. Ed. Engl. 1993, 32, 1042. Milne, D.; Murphy, P. J. J. Chem. Soc., Chem. Commun. 1993, 884.
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68. Ruck, K. Angew. Chem., Int. Ed. Engl. 1995, 34, 433. Vadecard, J.; Plaquevent, J.-C.; Duhamel, L.; Duhamel, P. J. Org. Chem. 1994, 59, 2285. Malmvik, A. C.; Obenius, U.; Henriksson, U. J. Chem. Soc., Perkin Trans. 2 1986, 1899. Boireau, G.; Abenhaim, D.; Henry-Basch, E. Tetrahedron 1979, 35, 1457. Gerlach, U.; Haubenreich, T.; Huenig, S. Chem. Ber. 1994, 127, 1969. Kumamoto, T.; Aoki, S.; Nakajima, M.; Koga, K. Tetrahedron: Asymmetry 1994, 5, 1431. Coote, S. J.; Davies, S. G.; Goodfellow, C. L.; Sutton, K. H.; Middlemiss, D.; Naylor, A. Tetrahedron: Asymmetry 1990, 1, 817. Kawasaki, M.; Terashima, S.
69. Ruck, K. Angew. Chem., Int. Ed. Engl. 1995, 34, 433. Vadecard, J.; Plaquevent, J.-C.; Duhamel, L.; Duhamel, P. J. Org. Chem. 1994, 59, 2285. Malmvik, A. C.; Obenius, U.; Henriksson, U. J. Chem. Soc., Perkin Trans. 2 1986, 1899. Boireau, G.; Abenhaim, D.; Henry-Basch, E. Tetrahedron 1979, 35, 1457. Gerlach, U.; Haubenreich, T.; Huenig, S. Chem. Ber. 1994, 127, 1969. Kumamoto, T.; Aoki, S.; Nakajima, M.; Koga, K. Tetrahedron: Asymmetry 1994, 5, 1431. Coote, S. J.; Davies, S. G.; Goodfellow, C. L.; Sutton, K. H.; Middlemiss, D.; Naylor, A. Tetrahedron: Asymmetry 1990, 1, 817. Kawasaki, M.; Terashima, S. Chem. Pharm. Bull. 1985, 33, 347. Fehr, C.; Stempf, I.; Galindo, J. Angew. Chem., Int. Ed. Engl. 1993, 32, 1042. Milne, D.; Murphy, P. J. J. Chem. Soc., Chem. Commun. 1993, 884.
70. For excellent discussions and leading references to mixed aggregation, see: Jackman, L. M.; Rakiewicz, E. F. J. Am. Chem. Soc. 1991, 113, 1202. Kremer, T.; Harder, S.; Junge, M.; Schleyer, P. v. R. Organometallics 1996, 15, 585. Also, see refs 15 and 26.
71. For excellent discussions and leading references to mixed aggregation, see: Jackman, L. M.; Rakiewicz, E. F. J. Am. Chem. Soc. 1991, 113, 1202. Kremer, T.; Harder, S.; Junge, M.; Schleyer, P. v. R. Organometallics 1996, 15, 585. Also, see refs 15 and 26.
72. For investigations of RLi/ROLi mixed aggregation, see: McGarrity, J. F.; Ogle, C. A. J. Am. Chem. Soc. 1985, 107, 1805. McGarrity, J. F.; Ogle, C. A. J. Am. Chem. Soc. 1985, 107, 1810. Marsch, M.; Harms, K.; Lochmann, L.; Boche, G. Angew. Chem., Int. Ed. Engl. 1990, 29, 308. Darensbourg, M. Y.; Kimura, B. Y.; Hartwell, G. E.; Brown, T. L. J. Am. Chem. Soc. 1970, 92, 1236. Seitz, L. M.; Brown, T. L. J. Am. Chem. Soc. 1966, 88, 2174. Lochmann, L.; Pospisil, J.; Vodnansky, J.; Trekoval, J.; Lim, D. Collect. Czech. Chem. Commun. 1965, 30, 2187. Saá, J. M.; Martorelli, G.; Frontera, A. J. Org. Chem. 1996, 61, 5194. Also, see refs 25 and 26.
73. For investigations of RLi/ROLi mixed aggregation, see: McGarrity, J. F.; Ogle, C. A. J. Am. Chem. Soc. 1985, 107, 1805. McGarrity, J. F.; Ogle, C. A. J. Am. Chem. Soc. 1985, 107, 1810. Marsch, M.; Harms, K.; Lochmann, L.; Boche, G. Angew. Chem., Int. Ed. Engl. 1990, 29, 308. Darensbourg, M. Y.; Kimura, B. Y.; Hartwell, G. E.; Brown, T. L. J. Am. Chem. Soc. 1970, 92, 1236. Seitz, L. M.; Brown, T. L. J. Am. Chem. Soc. 1966, 88, 2174. Lochmann, L.; Pospisil, J.; Vodnansky, J.; Trekoval, J.; Lim, D. Collect. Czech. Chem. Commun. 1965, 30, 2187. Saá, J. M.; Martorelli, G.; Frontera, A. J. Org. Chem. 1996, 61, 5194. Also, see refs 25 and 26.
74. For investigations of RLi/ROLi mixed aggregation, see: McGarrity, J. F.; Ogle, C. A. J. Am. Chem. Soc. 1985, 107, 1805. McGarrity, J. F.; Ogle, C. A. J. Am. Chem. Soc. 1985, 107, 1810. Marsch, M.; Harms, K.; Lochmann, L.; Boche, G. Angew. Chem., Int. Ed. Engl. 1990, 29, 308. Darensbourg, M. Y.; Kimura, B. Y.; Hartwell, G. E.; Brown, T. L. J. Am. Chem. Soc. 1970, 92, 1236. Seitz, L. M.; Brown, T. L. J. Am. Chem. Soc. 1966, 88, 2174. Lochmann, L.; Pospisil, J.; Vodnansky, J.; Trekoval, J.; Lim, D. Collect. Czech. Chem. Commun. 1965, 30, 2187. Saá, J. M.; Martorelli, G.; Frontera, A. J. Org. Chem. 1996, 61, 5194. Also, see refs 25 and 26.
75. For investigations of RLi/ROLi mixed aggregation, see: McGarrity, J. F.; Ogle, C. A. J. Am. Chem. Soc. 1985, 107, 1805. McGarrity, J. F.; Ogle, C. A. J. Am. Chem. Soc. 1985, 107, 1810. Marsch, M.; Harms, K.; Lochmann, L.; Boche, G. Angew. Chem., Int. Ed. Engl. 1990, 29, 308. Darensbourg, M. Y.; Kimura, B. Y.; Hartwell, G. E.; Brown, T. L. J. Am. Chem. Soc. 1970, 92, 1236. Seitz, L. M.; Brown, T. L. J. Am. Chem. Soc. 1966, 88, 2174. Lochmann, L.; Pospisil, J.; Vodnansky, J.; Trekoval, J.; Lim, D. Collect. Czech. Chem. Commun. 1965, 30, 2187. Saá, J. M.; Martorelli, G.; Frontera, A. J. Org. Chem. 1996, 61, 5194. Also, see refs 25 and 26.
76. For investigations of RLi/ROLi mixed aggregation, see: McGarrity, J. F.; Ogle, C. A. J. Am. Chem. Soc. 1985, 107, 1805. McGarrity, J. F.; Ogle, C. A. J. Am. Chem. Soc. 1985, 107, 1810. Marsch, M.; Harms, K.; Lochmann, L.; Boche, G. Angew. Chem., Int. Ed. Engl. 1990, 29, 308. Darensbourg, M. Y.; Kimura, B. Y.; Hartwell, G. E.; Brown, T. L. J. Am. Chem. Soc. 1970, 92, 1236. Seitz, L. M.; Brown, T. L. J. Am. Chem. Soc. 1966, 88, 2174. Lochmann, L.; Pospisil, J.; Vodnansky, J.; Trekoval, J.; Lim, D. Collect. Czech. Chem. Commun. 1965, 30, 2187. Saá, J. M.; Martorelli, G.; Frontera, A. J. Org. Chem. 1996, 61, 5194. Also, see refs 25 and 26.
77. For investigations of RLi/ROLi mixed aggregation, see: McGarrity, J. F.; Ogle, C. A. J. Am. Chem. Soc. 1985, 107, 1805. McGarrity, J. F.; Ogle, C. A. J. Am. Chem. Soc. 1985, 107, 1810. Marsch, M.; Harms, K.; Lochmann, L.; Boche, G. Angew. Chem., Int. Ed. Engl. 1990, 29, 308. Darensbourg, M. Y.; Kimura, B. Y.; Hartwell, G. E.; Brown, T. L. J. Am. Chem. Soc. 1970, 92, 1236. Seitz, L. M.; Brown, T. L. J. Am. Chem. Soc. 1966, 88, 2174. Lochmann, L.; Pospisil, J.; Vodnansky, J.; Trekoval, J.; Lim, D. Collect. Czech. Chem. Commun. 1965, 30, 2187. Saá, J. M.; Martorelli, G.; Frontera, A. J. Org. Chem. 1996, 61, 5194. Also, see refs 25 and 26.
78. For investigations of RLi/ROLi mixed aggregation, see: McGarrity, J. F.; Ogle, C. A. J. Am. Chem. Soc. 1985, 107, 1805. McGarrity, J. F.; Ogle, C. A. J. Am. Chem. Soc. 1985, 107, 1810. Marsch, M.; Harms, K.; Lochmann, L.; Boche, G. Angew. Chem., Int. Ed. Engl. 1990, 29, 308. Darensbourg, M. Y.; Kimura, B. Y.; Hartwell, G. E.; Brown, T. L. J. Am. Chem. Soc. 1970, 92, 1236. Seitz, L. M.; Brown, T. L. J. Am. Chem. Soc. 1966, 88, 2174. Lochmann, L.; Pospisil, J.; Vodnansky, J.; Trekoval, J.; Lim, D. Collect. Czech. Chem. Commun. 1965, 30, 2187. Saá, J. M.; Martorelli, G.; Frontera, A. J. Org. Chem. 1996, 61, 5194. Also, see refs 25 and 26.
79. Thomas, R. D.; Clarke, M. T.; Jensen, R. M.; Young, T. C. Organometallics 1986, 5, 1851. DeLong, G. T.; Pannell, D. K.; Clarke, M. T.; Thomas, R. D. J. Am. Chem. Soc. 1993, 115, 7013. Bates, T. F.; Clarke, M. T.; Thomas, R. D. J. Am. Chem. Soc. 1988, 110, 5109.
80. Thomas, R. D.; Clarke, M. T.; Jensen, R. M.; Young, T. C. Organometallics 1986, 5, 1851. DeLong, G. T.; Pannell, D. K.; Clarke, M. T.; Thomas, R. D. J. Am. Chem. Soc. 1993, 115, 7013. Bates, T. F.; Clarke, M. T.; Thomas, R. D. J. Am. Chem. Soc. 1988, 110, 5109.
81. Thomas, R. D.; Clarke, M. T.; Jensen, R. M.; Young, T. C. Organometallics 1986, 5, 1851. DeLong, G. T.; Pannell, D. K.; Clarke, M. T.; Thomas, R. D. J. Am. Chem. Soc. 1993, 115, 7013. Bates, T. F.; Clarke, M. T.; Thomas, R. D. J. Am. Chem. Soc. 1988, 110, 5109.
82. For theoretical investigations of RLi/ROLi mixed aggregates, see: Morey, J.; Costa, A.; Deyá, P. M.; Suñer, G.; Saá, J. M. J. Org. Chem. 1990, 55, 3902. Sorger, K.; Schleyer, P. v. R.; Stalke, D. J. Am. Chem. Soc. 1996, 118, 6924.
83. For theoretical investigations of RLi/ROLi mixed aggregates, see: Morey, J.; Costa, A.; Deyá, P. M.; Suñer, G.; Saá, J. M. J. Org. Chem. 1990, 55, 3902. Sorger, K.; Schleyer, P. v. R.; Stalke, D. J. Am. Chem. Soc. 1996, 118, 6924.
84. Schmitz, R. F.; Dekanter, F. J. J.; Schakel, M.; Klumpp, G. W. Tetrahedron 1994, 50, 5933.
85. (a) For an example of a LiBr/chelating alkoxide mixed aggregate, see: van der Schaaf, P. A.; Hogerheide, M. P.; Grove, D. M.; Spek, A. L.; van Koten, G. J. Chem. Soc., Chem. Commun. 1992, 1703. (b) For an example of a lithium acetylide/LiBr mixed aggregate, see: Reich, H. J.; Eisenhart, E. K.; Olson, R. E.; Kelly, M. J. J. Am. Chem. Soc. 1986, 108, 7791.
86. (a) For an example of a LiBr/chelating alkoxide mixed aggregate, see: van der Schaaf, P. A.; Hogerheide, M. P.; Grove, D. M.; Spek, A. L.; van Koten, G. J. Chem. Soc., Chem. Commun. 1992, 1703. (b) For an example of a lithium acetylide/LiBr mixed aggregate, see: Reich, H. J.; Eisenhart, E. K.; Olson, R. E.; Kelly, M. J. J. Am. Chem. Soc. 1986, 108, 7791.
87. Wijkens, P.; van Koten, E. M.; Janssen, M. D.; Jastrzebski, T. B. H.; Spek, A. L.; van Koten, G. Angew. Chem., Int. Ed. Engl. 1995, 34, 219.
88. (a) Goralski, P.; Legoff, D.; Chabanel, M. J. Organomet. Chem. 1993, 456, 1.
89. (b) Corruble, A.; Valnot, J.-Y.; Maddaluno, J.; Prigent, Y.; Davoust, D.; Duhamel, D. J. Am. Chem. Soc. 1997, 119, 10042.
90. (c) Hilmersson, G.; Ahlberg, P.; Davidsson, O. J. Am. Chem. Soc. 1996, 118, 3539.
91. 13C]cyclopropylacetylene was prepared as described in the Supporting Information.
92. 15N]3b) was prepared as described in the Supporting Information.
93. For solution structural studies of lithium acetylide, see: (a) Fraenkel, G.; Stier, M. Prepr. Am. Chem. Soc., Div. Pet. Chem. 1985, 30, 586. (b) Fraenkel G.; Pramanik, P. J. Chem. Soc., Chem. Commun. 1983, 1527. (c) Hässig, v. R.; Seebach, D. Helv. Chim. Acta 1983, 66, 2269. (d) Bauer, W.; Seebach, D. Helv. Chim. Acta 1984, 67, 1972. (e) Jackman, L. M.; Scarmoutzos, L. M.; DeBrosse, C. W. J. Am. Chem. Soc. 1987, 109, 5355. (f) Gareyev, R.; Streitwieser, A. J. Org. Chem. 1996, 61, 1742. (g) See also ref 30.
94. For solution structural studies of lithium acetylide, see: (a) Fraenkel, G.; Stier, M. Prepr. Am. Chem. Soc., Div. Pet. Chem. 1985, 30, 586. (b) Fraenkel G.; Pramanik, P. J. Chem. Soc., Chem. Commun. 1983, 1527. (c) Hässig, v. R.; Seebach, D. Helv. Chim. Acta 1983, 66, 2269. (d) Bauer, W.; Seebach, D. Helv. Chim. Acta 1984, 67, 1972. (e) Jackman, L. M.; Scarmoutzos, L. M.; DeBrosse, C. W. J. Am. Chem. Soc. 1987, 109, 5355. (f) Gareyev, R.; Streitwieser, A. J. Org. Chem. 1996, 61, 1742. (g) See also ref 30.
95. For solution structural studies of lithium acetylide, see: (a) Fraenkel, G.; Stier, M. Prepr. Am. Chem. Soc., Div. Pet. Chem. 1985, 30, 586. (b) Fraenkel G.; Pramanik, P. J. Chem. Soc., Chem. Commun. 1983, 1527. (c) Hässig, v. R.; Seebach, D. Helv. Chim. Acta 1983, 66, 2269. (d) Bauer, W.; Seebach, D. Helv. Chim. Acta 1984, 67, 1972. (e) Jackman, L. M.; Scarmoutzos, L. M.; DeBrosse, C. W. J. Am. Chem. Soc. 1987, 109, 5355. (f) Gareyev, R.; Streitwieser, A. J. Org. Chem. 1996, 61, 1742. (g) See also ref 30.
96. For solution structural studies of lithium acetylide, see: (a) Fraenkel, G.; Stier, M. Prepr. Am. Chem. Soc., Div. Pet. Chem. 1985, 30, 586. (b) Fraenkel G.; Pramanik, P. J. Chem. Soc., Chem. Commun. 1983, 1527. (c) Hässig, v. R.; Seebach, D. Helv. Chim. Acta 1983, 66, 2269. (d) Bauer, W.; Seebach, D. Helv. Chim. Acta 1984, 67, 1972. (e) Jackman, L. M.; Scarmoutzos, L. M.; DeBrosse, C. W. J. Am. Chem. Soc. 1987, 109, 5355. (f) Gareyev, R.; Streitwieser, A. J. Org. Chem. 1996, 61, 1742. (g) See also ref 30.
97. For solution structural studies of lithium acetylide, see: (a) Fraenkel, G.; Stier, M. Prepr. Am. Chem. Soc., Div. Pet. Chem. 1985, 30, 586. (b) Fraenkel G.; Pramanik, P. J. Chem. Soc., Chem. Commun. 1983, 1527. (c) Hässig, v. R.; Seebach, D. Helv. Chim. Acta 1983, 66, 2269. (d) Bauer, W.; Seebach, D. Helv. Chim. Acta 1984, 67, 1972. (e) Jackman, L. M.; Scarmoutzos, L. M.; DeBrosse, C. W. J. Am. Chem. Soc. 1987, 109, 5355. (f) Gareyev, R.; Streitwieser, A. J. Org. Chem. 1996, 61, 1742. (g) See also ref 30.
98. For solution structural studies of lithium acetylide, see: (a) Fraenkel, G.; Stier, M. Prepr. Am. Chem. Soc., Div. Pet. Chem. 1985, 30, 586. (b) Fraenkel G.; Pramanik, P. J. Chem. Soc., Chem. Commun. 1983, 1527. (c) Hässig, v. R.; Seebach, D. Helv. Chim. Acta 1983, 66, 2269. (d) Bauer, W.; Seebach, D. Helv. Chim. Acta 1984, 67, 1972. (e) Jackman, L. M.; Scarmoutzos, L. M.; DeBrosse, C. W. J. Am. Chem. Soc. 1987, 109, 5355. (f) Gareyev, R.; Streitwieser, A. J. Org. Chem. 1996, 61, 1742. (g) See also ref 30.
99. For lithium acetylide X-ray crystal structures, see: Schubert, B.; Weiss, E. Angew. Chem., Int. Ed. Engl. 1983, 22, 496. Schubert, B.; Weiss, E. Chem. Ber. 1983, 116, 3212. Seebach, D.; Hässig, v. R.; Gabriel, J. Helv. Chim. Acta 1983, 66, 308. Geissler, M.; Kopf, J.; Schubert, B.; Weiss, E.; Neugebauer, W.; Schleyer, P. v. R. Angew. Chem., Int. Ed. Engl. 1987, 26, 587.
100. For lithium acetylide X-ray crystal structures, see: Schubert, B.; Weiss, E. Angew. Chem., Int. Ed. Engl. 1983, 22, 496. Schubert, B.; Weiss, E. Chem. Ber. 1983, 116, 3212. Seebach, D.; Hässig, v. R.; Gabriel, J. Helv. Chim. Acta 1983, 66, 308. Geissler, M.; Kopf, J.; Schubert, B.; Weiss, E.; Neugebauer, W.; Schleyer, P. v. R. Angew. Chem., Int. Ed. Engl. 1987, 26, 587.
101. For lithium acetylide X-ray crystal structures, see: Schubert, B.; Weiss, E. Angew. Chem., Int. Ed. Engl. 1983, 22, 496. Schubert, B.; Weiss, E. Chem. Ber. 1983, 116, 3212. Seebach, D.; Hässig, v. R.; Gabriel, J. Helv. Chim. Acta 1983, 66, 308. Geissler, M.; Kopf, J.; Schubert, B.; Weiss, E.; Neugebauer, W.; Schleyer, P. v. R. Angew. Chem., Int. Ed. Engl. 1987, 26, 587.
102. For lithium acetylide X-ray crystal structures, see: Schubert, B.; Weiss, E. Angew. Chem., Int. Ed. Engl. 1983, 22, 496. Schubert, B.; Weiss, E. Chem. Ber. 1983, 116, 3212. Seebach, D.; Hässig, v. R.; Gabriel, J. Helv. Chim. Acta 1983, 66, 308. Geissler, M.; Kopf, J.; Schubert, B.; Weiss, E.; Neugebauer, W.; Schleyer, P. v. R. Angew. Chem., Int. Ed. Engl. 1987, 26, 587.
103. For theoretical studies of lithium acetylides, see: Bachrach, S. M.; Streitwieser, A., Jr. J. Am. Chem. Soc. 1984, 106, 2283. Bühl, M.; van Eikema Hommes, N. J. R.; Schleyer, P. v. R.; Fleischer, U.; Kutzelnigg, W. J. Am. Chem. Soc. 1991, 113, 2459. Ritchie, J. P. Tetrahedron Lett. 1982, 23, 4999. Jemmis, E. D.; Chandrasekhar, J.; Schleyer, P. v. R. J. Am. Chem. Soc. 1979, 101, 2848. Dorigo, A. E.; van Eikema Hommes, N. J. R.; Krogh-Jespersen, K.; Schleyer, P. v. R. Angew. Chem., Int. Ed. Engl. 1992, 31, 1602. Also, see refs 33f and 52.
104. For theoretical studies of lithium acetylides, see: Bachrach, S. M.; Streitwieser, A., Jr. J. Am. Chem. Soc. 1984, 106, 2283. Bühl, M.; van Eikema Hommes, N. J. R.; Schleyer, P. v. R.; Fleischer, U.; Kutzelnigg, W. J. Am. Chem. Soc. 1991, 113, 2459. Ritchie, J. P. Tetrahedron Lett. 1982, 23, 4999. Jemmis, E. D.; Chandrasekhar, J.; Schleyer, P. v. R. J. Am. Chem. Soc. 1979, 101, 2848. Dorigo, A. E.; van Eikema Hommes, N. J. R.; Krogh-Jespersen, K.; Schleyer, P. v. R. Angew. Chem., Int. Ed. Engl. 1992, 31, 1602. Also, see refs 33f and 52.
105. For theoretical studies of lithium acetylides, see: Bachrach, S. M.; Streitwieser, A., Jr. J. Am. Chem. Soc. 1984, 106, 2283. Bühl, M.; van Eikema Hommes, N. J. R.; Schleyer, P. v. R.; Fleischer, U.; Kutzelnigg, W. J. Am. Chem. Soc. 1991, 113, 2459. Ritchie, J. P. Tetrahedron Lett. 1982, 23, 4999. Jemmis, E. D.; Chandrasekhar, J.; Schleyer, P. v. R. J. Am. Chem. Soc. 1979, 101, 2848. Dorigo, A. E.; van Eikema Hommes, N. J. R.; Krogh-Jespersen, K.; Schleyer, P. v. R. Angew. Chem., Int. Ed. Engl. 1992, 31, 1602. Also, see refs 33f and 52.
106. For theoretical studies of lithium acetylides, see: Bachrach, S. M.; Streitwieser, A., Jr. J. Am. Chem. Soc. 1984, 106, 2283. Bühl, M.; van Eikema Hommes, N. J. R.; Schleyer, P. v. R.; Fleischer, U.; Kutzelnigg, W. J. Am. Chem. Soc. 1991, 113, 2459. Ritchie, J. P. Tetrahedron Lett. 1982, 23, 4999. Jemmis, E. D.; Chandrasekhar, J.; Schleyer, P. v. R. J. Am. Chem. Soc. 1979, 101, 2848. Dorigo, A. E.; van Eikema Hommes, N. J. R.; Krogh-Jespersen, K.; Schleyer, P. v. R. Angew. Chem., Int. Ed. Engl. 1992, 31, 1602. Also, see refs 33f and 52.
107. For theoretical studies of lithium acetylides, see: Bachrach, S. M.; Streitwieser, A., Jr. J. Am. Chem. Soc. 1984, 106, 2283. Bühl, M.; van Eikema Hommes, N. J. R.; Schleyer, P. v. R.; Fleischer, U.; Kutzelnigg, W. J. Am. Chem. Soc. 1991, 113, 2459. Ritchie, J. P. Tetrahedron Lett. 1982, 23, 4999. Jemmis, E. D.; Chandrasekhar, J.; Schleyer, P. v. R. J. Am. Chem. Soc. 1979, 101, 2848. Dorigo, A. E.; van Eikema Hommes, N. J. R.; Krogh-Jespersen, K.; Schleyer, P. v. R. Angew. Chem., Int. Ed. Engl. 1992, 31, 1602. Also, see refs 33f and 52.
108. For a general discussion of metal acetylides, see: Manna, J.; John, K. D.; Hopkins, M. D. Adv. Organomet. Chem. 1995, 38, 79.
109. Trisolvated dimers have been observed, but seem unlikely. For leading references, see: Depue, J. S.; Collum, D. B. J. Am. Chem. Soc. 1988, 110, 5518. Legzdins, P.; Sayers, S. F. Organometallics 1996, 15, 3907.
110. Trisolvated dimers have been observed, but seem unlikely. For leading references, see: Depue, J. S.; Collum, D. B. J. Am. Chem. Soc. 1988, 110, 5518. Legzdins, P.; Sayers, S. F. Organometallics 1996, 15, 3907.
111. Rapid infra-aggregate exchange can cause coupling to all nuclei within the aggregate. For leading references, see: Bauer, W. J. Am. Chem. Soc. 1996, 118, 5450. See also ref 25.
112. Günther, H.; Moskau, D.; Bast, P.; Schmalz, D. Angew. Chem., Int. Ed. Engl. 1987, 26, 1212.
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117. 25,41
118. Amino alcohol/amino alkoxide complexes analogous to 11 and 12 may be important in asymmetric protonations: Fehr, C. Angew. Chem., Int. Ed. Engl. 1996 35, 2567.
119. 6Li resonances will appear as multiplets, manifesting from two to eight lines.
120. For example, see: Reich, H. J.; Gudmundsson, B. Ö. J. Am. Chem. Soc. 1996, 118, 6074.
121. For leading references to detectable organolithium-substrate precomplexation, see: ref 18d. For a general discussion of ketone-lithium complexation and related ketone-Lewis acid complexation, see: Shambayati, S.; Schreiber, S. L. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: New York, 1991; Vol. 1, p 283.
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126. Glaser, R.; Streitwieser, A., Jr. THEOCHEM 1988, 163, 19. Schleyer, P. v. R. Pure Appl. Chem. 1984, 56, 151.
127. For leading references, see: Reich, H. J.; Kulicke, K. J. Am. Chem. Soc. 1996, 118, 273.
128. Sato, D.; Kawasaki, H.; Shimada, I.; Arata, Y.; Okamura, K.; Date, T.; Koga, K. J. Am. Chem. Soc. 1992, 114, 761.
129. Hilmersson, G.; Davidsson, O. Organometallics 1995, 14, 912.
130. For a superb discussion and extensive leading references to lithium acetylene π interactions, see: Goldfuss, B.; Schleyer, P. v. R.; Hampel, F. J. Am. Chem. Soc. 1997, 119, 1072. See also: Lucht, B. L.; Collum, D. B. J. Am. Chem. Soc. 1996, 118, 2217 and ref 33f.
131. For a superb discussion and extensive leading references to lithium acetylene π interactions, see: Goldfuss, B.; Schleyer, P. v. R.; Hampel, F. J. Am. Chem. Soc. 1997, 119, 1072. See also: Lucht, B. L.; Collum, D. B. J. Am. Chem. Soc. 1996, 118, 2217 and ref 33f.
132. Remenar, J. F.; Collum, D. B. J. Am. Chem. Soc. 1997, 119, 5517.
133. Bachrach, S. M.; Streitwieser, A., Jr. J. Am. Chem. Soc. 1986, 108. 3946. See also: ref 55.
134. Open dimer-based mechanisms for 1,2-additions of alkyllithiums have been investigated computationally: Kaufmann, E.; Schleyer, P. v. R.; Houk, K. N.; Wu, Y.-D. J. Am. Chem. Soc. 1985, 107, 5560. Nakamura, E.; Nakamura, M.; Koga, N.; Morokuma, K. J. Am. Chem. Soc. 1993, 115, 11016.
135. Open dimer-based mechanisms for 1,2-additions of alkyllithiums have been investigated computationally: Kaufmann, E.; Schleyer, P. v. R.; Houk, K. N.; Wu, Y.-D. J. Am. Chem. Soc. 1985, 107, 5560. Nakamura, E.; Nakamura, M.; Koga, N.; Morokuma, K. J. Am. Chem. Soc. 1993, 115, 11016.
136. For leading references to other investigations and discussions of open dimer-based mechanisms, see: Romesberg, F. E.; Collum, D. B. J. Am. Chem. Soc. 1994, 116, 9187. Henderson, K. W.; Dongo, A. E.; Liu, Q.-Y.; Williard, P. G.; Schleyer, P. v. R.; Bernstein, P. R. J. Am. Chem. Soc. 1996, 118, 1339.
137. For leading references to other investigations and discussions of open dimer-based mechanisms, see: Romesberg, F. E.; Collum, D. B. J. Am. Chem. Soc. 1994, 116, 9187. Henderson, K. W.; Dongo, A. E.; Liu, Q.-Y.; Williard, P. G.; Schleyer, P. v. R.; Bernstein, P. R. J. Am. Chem. Soc. 1996, 118, 1339.
138. 3 cause a confusing reversal in the si-re notations.
139. For a discussion and leading references to F-Li interactions, see: Barbarich, T. J.; Handy, S. T.; Miller, S. M.; Andersen, O. P.; Grieco, P. A.; Strauss, S. H. Organometallics 1996, 15, 3776.
140. Bickelhaupt, F. M.; Hoffmann, R. Unpublished results.
141. For an interesting discussion of and leading references to hydrogen bonding in organometallic complexes, see: Kapteijn, G. M.; Dervisi, A.; Grove, D. M.; Kooijman, H.; Lakin, M. T.; Spek, A. L.; van Koten, G. J. Am. Chem. Soc. 1995, 117, 10939.
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143. Whitesell, J. K. Chem. Rev. 1989, 89, 1581. Noyori, R. Asymmetric Catalysis in Organic Synthesis; John Wiley: New York, 1994.
144. For rate studies of 1,2-additions, see: Smith, S. G. J. Org. Chem. 1985, 50, 2715 and references therein.