Structural consequences of the addition of lithium halides in enolization and aldol reactions

Journal of the American Chemical Society

Volumn 118, Issue 6, 1996, Pages 1339-1347

  Henderson, Kenneth W ^a   Dorigo, Andrea E ^a   Liu, Qi Yong ^a   Williard, Paul G ^a   Schleyer, Paul Von Ragué ^b   Bernstein, Peter R ^c  

^a BROWN UNIVERSITY   (United States)

^b UNIVERSITY OF ERLANGEN NUREMBERG   (Germany)

^c ASTRAZENECA   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

ORGANOLITHIUM COMPOUND;

ARTICLE; COMPLEX FORMATION; DRUG STRUCTURE; DRUG SYNTHESIS; NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; STEREOCHEMISTRY; THEORY; X RAY DIFFRACTION;

EID: 0029966049     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja9527838     Document Type: Article

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49. max = 47°, 4843 measured reflections, 3965 independent reflections, 3965 reflections used in the refinement, R(1) = 0.0424, wR(1) = 0.0766.
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57. Li-H interactions have been noted in other structures including: (a) Chen, H.; Bartlett, R. A.; Dias, H. V. R.; Olmstead, M. M.; Power, P. P. Organometallics 1991, 30, 2487. (b) Barr, D.; Clegg, W.; Mulvey, R. E.; Snaith, R. J. Chem. Soc., Chem. Commun. 1984, 285, 287.
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64. max = 47°, 5839 measured reflections, 5561 independent reflections, 5561 reflections used in the refinement, R(1) = 0.0414, wR(1) = 0.0950.
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66. (b) Romesberg, F. E.; Collum, D. B. J. Am. Chem. Soc. 1994, 116, 9198.
67. max = 45°, 6454 measured reflections, 5236 independent reflections, 5235 reflections used in the refinement. R(1) = 0.0857, wR(1) = 0.2103.
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70. max = 45°, 4265 measured reflections, 3384 independent reflections, 3383 reflections used in the refinement. R(1) = 0.0667, wR(1) = 0.1062.
71. max = 50°. 5829 measured reflections, 4716 independent reflections, 4714 reflections used in the refinement. R(1) = 0.0515, wR(1) = 0.1173.
72. Raston, C. L.; Skelton, B. W.; Whitaker, C. R.; White, A. H. Aust. J. Chem. 1988, 41, 1925. Disorder for compound 8 led to relatively poor refinement of the structure. We crystallized compound 8 under solvent conditions different from those descibed in the above reference and were able to refine the structure to an R value of 0.0515% from a triclinic cell. The values quoted in Table 1 refer to our data.
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82. The Gaussian 92 program was used for all calculations described here: Frisch, M. J.; Trucks, G. W.; Head-Gordon, M.; Gill, P. M. W.; Wong, M. W.; Foresman, J. B.; Johnson, B. G.; Schlegel, H. B.; Robb, M. A.; Replogle, E. S.; Gomperts, R.; Andres, J. L.; Raghavachari, K.; Binkley, J. S.; Gonzalez, C.; Martin, R. L.; Fox, D. J.; DeFrees, D. J.; Baker, J.; Stewart, J. J. P.; Pople, J. A. Gaussian 92. Gaussian, Inc.: Pittsburgh, PA, 1992.
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85. -1 below III′.
86. Stewart, J. J. P. MOPAC, Version 6.0. For the PM3 parameterization of lithium, see: Anders, E.; Koch, R.; Freunscht, P. J. Comput. Chem. 1993, 14, 1301. The keyword PRECISE was used for the optimizations.
87. Stewart, J. J. P. MOPAC, Version 6.0. For the PM3 parameterization of lithium, see: Anders, E.; Koch, R.; Freunscht, P. J. Comput. Chem. 1993, 14, 1301. The keyword PRECISE was used for the optimizations.
88. 3, -176.02400: VI, -350.11979: VII, -489.785 53.
89. For comparison, the charge on Br in the homodimer II is -0.86. Natural charges were calculated by means of the NBO program (incorporated in Gaussian 92 as Link 607): (a) Glendening, E. D.; Reed, A. E.; Carpenter, J. E.; Weinhold, F. NBO Version 3.1. See also: (b) Reed, A. E.; Weinhold, F. J. Chem. Phys. 1983, 78, 4066.
90. For comparison, the charge on Br in the homodimer II is -0.86. Natural charges were calculated by means of the NBO program (incorporated in Gaussian 92 as Link 607): (a) Glendening, E. D.; Reed, A. E.; Carpenter, J. E.; Weinhold, F. NBO Version 3.1. See also: (b) Reed, A. E.; Weinhold, F. J. Chem. Phys. 1983, 78, 4066.