Synthesis of all Three Regioisomers of Pyridylalanine

Synlett

Volumn 1997, Issue 2, 1997, Pages 169-170

  Walker, Michael A ^a   Kaplita, Khane Pham ^a   Chen, Ti ^a   King, H Dalton ^a  

^a BRISTOL MYERS SQUIBB   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0039267611     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1997-742     Document Type: Article

References (15)

1. Previous syntheses: a) Bozell, J. J.; Bogt, C. E.; Gozum, J.; J. Org. Chem. 1991, 56, 2584. b) Hoes, C.; Raap, J.; Bloemhoff, W.: Kerling, K. E. J.; Rec. Trav. Chim. 1980, 99. c) Hsieh, K.; Jorgensen, E. C.; Lee, T. C. J. Med. Chem. 1979, 22, 1199.
2. Previous syntheses: a) Bozell, J. J.; Bogt, C. E.; Gozum, J.; J. Org. Chem. 1991, 56, 2584. b) Hoes, C.; Raap, J.; Bloemhoff, W.: Kerling, K. E. J.; Rec. Trav. Chim. 1980, 99. c) Hsieh, K.; Jorgensen, E. C.; Lee, T. C. J. Med. Chem. 1979, 22, 1199.
3. Previous syntheses: a) Bozell, J. J.; Bogt, C. E.; Gozum, J.; J. Org. Chem. 1991, 56, 2584. b) Hoes, C.; Raap, J.; Bloemhoff, W.: Kerling, K. E. J.; Rec. Trav. Chim. 1980, 99. c) Hsieh, K.; Jorgensen, E. C.; Lee, T. C. J. Med. Chem. 1979, 22, 1199.
4. For a recent review on the synthesis of α-amino acids see: Duthaler, R. O. Tetrahedron 1994, 50, 1539.
5. Jackson, R. F. W, James, K., Wythes, M. J., Wood, A. J. Chem. Soc. Chem. Comm. 1989, 644.
6. Jackson, R. F. W., Wythes, M. J., Wood, A. Tetrahedron Lett. 1989, 30, 5941.
7. Tamura, Y.; Ochiai, H.; Nakamura, T.; Tsubaki, K.; Yoshida, Z. Tetrahedron Lett. 1985, 26, 5559.
8. AchyuthaRao, S.; Knochel, P. J. Org. Chem. 1991, 56, 4591.
9. 4: C, 59.99; H, 7.19; N, 9.99. Found: C, 60.12; H, 7.10; N, 9.79.
10. Dunn, M. J.; Jackson, R. F. W.; Pietruszka, J.; Turner, D. J. Org. Chem. 1995, 60, 2210.
11. 4: C, 59.99; H, 7.19; N, 9.99. Found: C, 59.97; H, 7.16; N, 9.72.
12. 4: C, 59.99; H, 7.19; N, 9.99. Found: C, 59.72,; H, 7.07; N, 9.58.
13. 2 (0.25 g) and 4-bromopyridine (1.32 g, 6.79 mmol) prepared according to the above procedure. The reaction was stirred for 5 hrs at 60°C and worked-up in the usual manner.
14. Rieke Metals, Inc., Lincoln Nebraska.
15. The putative zinc complex A might have a stronger field or inductive effect than the 2- or 3-pyridyl regioisomers due to resonance structure B and thus activate the α-postion towards deprotonation. (Equation Presented)