Acyclic stereoselective boron alkylation reactions for the asymmetric synthesis of β-substituted α-amino acid derivatives

Journal of the American Chemical Society

Volumn 125, Issue 9, 2003, Pages 2370-2371

  O'Donnell, Martin J ^a,b   Cooper, Jeremy T ^a,b   Mader, Mary M ^a,b  

^a INDIANA UNIVERSITY   (United States)

^b ELI LILLY AND COMPANY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALPHA AMINO ACID; BETA AMINO ACID; BORON; ORGANOBORON DERIVATIVE; STYRENE;

ALKYLATION; ARTICLE; CHEMICAL REACTION; ENANTIOMER; ENANTIOSELECTIVITY; HYDROBORATION; STEREOCHEMISTRY; SYNTHESIS;

EID: 0037420357     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja0298794     Document Type: Article

References (25)

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5. Recent stereoselective syntheses of β-substituted α-amino acids: (a) Medina, E.; Moyano, A.; Pericàs, M. A.; Riera, A. Helv. Chim. Acta 2000, 83, 972-988. (b) Tamura, O.; Yoshida, S.; Sugita, H.; Mita, N.; Uyama, Y.; Morita, N.; Ishiguro, M.; Kawasaki, T.; Ishibashi, H.; Sakamoto, M. Synlett 2000, 1553-1556. (c) Burtin, G.; Corringer, P.-J.; Young, D. W. J. Chem. Soc., Perkin Trans. 1 2000, 3451-3459. (d) Liang, B.; Carroll, P. J.; Joullié, M. M. Org. Lett. 2000, 2, 4157-4160. (e) Soloshonok, V. A.; Tang, X.; Hruby, V. J.; Van Meervelt, L. Org. Lett. 2001, 3, 341-343. (f) Bull, S. D.; Davies, S. G.; Garner, A. C.; Mujtaba, N. Synlett 2001, 781-784. (g) Han, G.; Lewis, A.; Hruby, V. J. Tetrahedron Lett. 2001, 42, 4601-4603. (h) Acevedo, C. M.; Kogut, E. F.; Lipton, M. A. Tetrahedron 2001, 57, 6353-6359.
6. Recent stereoselective syntheses of β-substituted α-amino acids: (a) Medina, E.; Moyano, A.; Pericàs, M. A.; Riera, A. Helv. Chim. Acta 2000, 83, 972-988. (b) Tamura, O.; Yoshida, S.; Sugita, H.; Mita, N.; Uyama, Y.; Morita, N.; Ishiguro, M.; Kawasaki, T.; Ishibashi, H.; Sakamoto, M. Synlett 2000, 1553-1556. (c) Burtin, G.; Corringer, P.-J.; Young, D. W. J. Chem. Soc., Perkin Trans. 1 2000, 3451-3459. (d) Liang, B.; Carroll, P. J.; Joullié, M. M. Org. Lett. 2000, 2, 4157-4160. (e) Soloshonok, V. A.; Tang, X.; Hruby, V. J.; Van Meervelt, L. Org. Lett. 2001, 3, 341-343. (f) Bull, S. D.; Davies, S. G.; Garner, A. C.; Mujtaba, N. Synlett 2001, 781-784. (g) Han, G.; Lewis, A.; Hruby, V. J. Tetrahedron Lett. 2001, 42, 4601-4603. (h) Acevedo, C. M.; Kogut, E. F.; Lipton, M. A. Tetrahedron 2001, 57, 6353-6359.
7. Recent stereoselective syntheses of β-substituted α-amino acids: (a) Medina, E.; Moyano, A.; Pericàs, M. A.; Riera, A. Helv. Chim. Acta 2000, 83, 972-988. (b) Tamura, O.; Yoshida, S.; Sugita, H.; Mita, N.; Uyama, Y.; Morita, N.; Ishiguro, M.; Kawasaki, T.; Ishibashi, H.; Sakamoto, M. Synlett 2000, 1553-1556. (c) Burtin, G.; Corringer, P.-J.; Young, D. W. J. Chem. Soc., Perkin Trans. 1 2000, 3451-3459. (d) Liang, B.; Carroll, P. J.; Joullié, M. M. Org. Lett. 2000, 2, 4157-4160. (e) Soloshonok, V. A.; Tang, X.; Hruby, V. J.; Van Meervelt, L. Org. Lett. 2001, 3, 341-343. (f) Bull, S. D.; Davies, S. G.; Garner, A. C.; Mujtaba, N. Synlett 2001, 781-784. (g) Han, G.; Lewis, A.; Hruby, V. J. Tetrahedron Lett. 2001, 42, 4601-4603. (h) Acevedo, C. M.; Kogut, E. F.; Lipton, M. A. Tetrahedron 2001, 57, 6353-6359.
8. Recent stereoselective syntheses of β-substituted α-amino acids: (a) Medina, E.; Moyano, A.; Pericàs, M. A.; Riera, A. Helv. Chim. Acta 2000, 83, 972-988. (b) Tamura, O.; Yoshida, S.; Sugita, H.; Mita, N.; Uyama, Y.; Morita, N.; Ishiguro, M.; Kawasaki, T.; Ishibashi, H.; Sakamoto, M. Synlett 2000, 1553-1556. (c) Burtin, G.; Corringer, P.-J.; Young, D. W. J. Chem. Soc., Perkin Trans. 1 2000, 3451-3459. (d) Liang, B.; Carroll, P. J.; Joullié, M. M. Org. Lett. 2000, 2, 4157-4160. (e) Soloshonok, V. A.; Tang, X.; Hruby, V. J.; Van Meervelt, L. Org. Lett. 2001, 3, 341-343. (f) Bull, S. D.; Davies, S. G.; Garner, A. C.; Mujtaba, N. Synlett 2001, 781-784. (g) Han, G.; Lewis, A.; Hruby, V. J. Tetrahedron Lett. 2001, 42, 4601-4603. (h) Acevedo, C. M.; Kogut, E. F.; Lipton, M. A. Tetrahedron 2001, 57, 6353-6359.
9. Recent stereoselective syntheses of β-substituted α-amino acids: (a) Medina, E.; Moyano, A.; Pericàs, M. A.; Riera, A. Helv. Chim. Acta 2000, 83, 972-988. (b) Tamura, O.; Yoshida, S.; Sugita, H.; Mita, N.; Uyama, Y.; Morita, N.; Ishiguro, M.; Kawasaki, T.; Ishibashi, H.; Sakamoto, M. Synlett 2000, 1553-1556. (c) Burtin, G.; Corringer, P.-J.; Young, D. W. J. Chem. Soc., Perkin Trans. 1 2000, 3451-3459. (d) Liang, B.; Carroll, P. J.; Joullié, M. M. Org. Lett. 2000, 2, 4157-4160. (e) Soloshonok, V. A.; Tang, X.; Hruby, V. J.; Van Meervelt, L. Org. Lett. 2001, 3, 341-343. (f) Bull, S. D.; Davies, S. G.; Garner, A. C.; Mujtaba, N. Synlett 2001, 781-784. (g) Han, G.; Lewis, A.; Hruby, V. J. Tetrahedron Lett. 2001, 42, 4601-4603. (h) Acevedo, C. M.; Kogut, E. F.; Lipton, M. A. Tetrahedron 2001, 57, 6353-6359.
10. Recent stereoselective syntheses of β-substituted α-amino acids: (a) Medina, E.; Moyano, A.; Pericàs, M. A.; Riera, A. Helv. Chim. Acta 2000, 83, 972-988. (b) Tamura, O.; Yoshida, S.; Sugita, H.; Mita, N.; Uyama, Y.; Morita, N.; Ishiguro, M.; Kawasaki, T.; Ishibashi, H.; Sakamoto, M. Synlett 2000, 1553-1556. (c) Burtin, G.; Corringer, P.-J.; Young, D. W. J. Chem. Soc., Perkin Trans. 1 2000, 3451-3459. (d) Liang, B.; Carroll, P. J.; Joullié, M. M. Org. Lett. 2000, 2, 4157-4160. (e) Soloshonok, V. A.; Tang, X.; Hruby, V. J.; Van Meervelt, L. Org. Lett. 2001, 3, 341-343. (f) Bull, S. D.; Davies, S. G.; Garner, A. C.; Mujtaba, N. Synlett 2001, 781-784. (g) Han, G.; Lewis, A.; Hruby, V. J. Tetrahedron Lett. 2001, 42, 4601-4603. (h) Acevedo, C. M.; Kogut, E. F.; Lipton, M. A. Tetrahedron 2001, 57, 6353-6359.
11. Recent stereoselective syntheses of β-substituted α-amino acids: (a) Medina, E.; Moyano, A.; Pericàs, M. A.; Riera, A. Helv. Chim. Acta 2000, 83, 972-988. (b) Tamura, O.; Yoshida, S.; Sugita, H.; Mita, N.; Uyama, Y.; Morita, N.; Ishiguro, M.; Kawasaki, T.; Ishibashi, H.; Sakamoto, M. Synlett 2000, 1553-1556. (c) Burtin, G.; Corringer, P.-J.; Young, D. W. J. Chem. Soc., Perkin Trans. 1 2000, 3451-3459. (d) Liang, B.; Carroll, P. J.; Joullié, M. M. Org. Lett. 2000, 2, 4157-4160. (e) Soloshonok, V. A.; Tang, X.; Hruby, V. J.; Van Meervelt, L. Org. Lett. 2001, 3, 341-343. (f) Bull, S. D.; Davies, S. G.; Garner, A. C.; Mujtaba, N. Synlett 2001, 781-784. (g) Han, G.; Lewis, A.; Hruby, V. J. Tetrahedron Lett. 2001, 42, 4601-4603. (h) Acevedo, C. M.; Kogut, E. F.; Lipton, M. A. Tetrahedron 2001, 57, 6353-6359.
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14. See Supporting Information for full experimental details.
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24. A conformational search of the lithium enolates corresponding to (3S)-9 and (3S)-7 was conducted by the Monte Carlo method, generating over 400 initial structures using MMFF94 in Spartan v. 5.1.3. The four lowest-energy conformers spanning an energy range of 12 kJ/mol were refined independently at PM3 and MNDO, and the geometries were then optimized at B3LYP/6-31G* using Jaguar. See Supporting Information for full details.
25. The lithium enolate generated by addition of -6 to 1 was calculated, and showed the same preference for the anti conformation by the four computational treatments.