The Birch reduction of 3-substituted pyrroles

Tetrahedron Letters

Volumn 39, Issue 19, 1998, Pages 3075-3078

  Donohoe, Timothy J ^a   Guyo, Paul M ^a   Harji, Rakesh R ^a   Helliwell, Madeleine ^a   Cousins, Rick P C ^b  

^a UNIVERSITY OF MANCHESTER   (United Kingdom)

^b GLAXOSMITHKLINE   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

AMIDE; AMMONIA; ESTER; METAL; PROLINE DERIVATIVE; PYRROLE DERIVATIVE; SODIUM;

ALKYLATION; ARTICLE; CHEMICAL REACTION; REDUCTION; X RAY CRYSTALLOGRAPHY;

EID: 0032492974     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)00362-1     Document Type: Article

References (16)

1. 1. Donohoe, T. J.; Garg, R.; Stevenson, C. A. Tetrahedron Asymmetry, 1996, 7, 317; Donohoe, T. J.; Helliwell, M.; Stevenson, C. A.; Ladduwahetty, T. Tetrahedron Lett., 1998, 39, 3071. see also ref 3.
2. 1. Donohoe, T. J.; Garg, R.; Stevenson, C. A. Tetrahedron Asymmetry, 1996, 7, 317; Donohoe, T. J.; Helliwell, M.; Stevenson, C. A.; Ladduwahetty, T. Tetrahedron Lett., 1998, 39, 3071. see also ref 3.
3. 2. For general reviews of the Birch reduction see: Mander, L. N. In Comprehensive Organic Synthesis; Ed. Trost, B. M.; Fleming, I.; Pergamon; New York; 1991, vol 8; Rabideau, P. W.; Marcinow, Z. Organic Reactions, 1992, 42, 1; Rabideau, P. W. Tetrahedron, 1989, 45, 1579.
4. 2. For general reviews of the Birch reduction see: Mander, L. N. In Comprehensive Organic Synthesis; Ed. Trost, B. M.; Fleming, I.; Pergamon; New York; 1991, vol 8; Rabideau, P. W.; Marcinow, Z. Organic Reactions, 1992, 42, 1; Rabideau, P. W. Tetrahedron, 1989, 45, 1579.
5. 2. For general reviews of the Birch reduction see: Mander, L. N. In Comprehensive Organic Synthesis; Ed. Trost, B. M.; Fleming, I.; Pergamon; New York; 1991, vol 8; Rabideau, P. W.; Marcinow, Z. Organic Reactions, 1992, 42, 1; Rabideau, P. W. Tetrahedron, 1989, 45, 1579.
6. 3. Donohoe, T. J.; Guyo, P. M. J. Org. Chem., 1996, 61, 7664; Donohoe, T. J.; Guyo, P. M.; Beddoes, R. L.; Helliwell, M. J. Chem. Soc., Perkin Trans. 1, 1998, in the press.
7. 3. Donohoe, T. J.; Guyo, P. M. J. Org. Chem., 1996, 61, 7664; Donohoe, T. J.; Guyo, P. M.; Beddoes, R. L.; Helliwell, M. J. Chem. Soc., Perkin Trans. 1, 1998, in the press.
8. 4. van Leusen, A. M.; Siderius, H.; Hoogenboom, B. E.; van Leusen, D. Tetrahedron Lett., 1972, 5337.
9. 5. Kinoshita, T.; Miwa, T. Carbohydrate Res., 1973, 28, 175; Kinoshita, T.; Miyano, K.; Miwa, T. Bull. Chem. Soc. Japan, 1975, 48, 1865; Kinoshita, T.; Miwa, T. Bull. Chem. Soc. Japan, 1978, 57, 225; Beddoes, R. L.; Lewis, M. L.; Gilbert, P.; Quayle, P.; Thompson, S. P.; Wang, S.; Mills, K. Tetrahedron Lett., 1996, 37, 9119; Kinoshita, T.; Ichinari, D.; Sinya, J. J. Het. Chem., 1996, 33, 1313.
10. 5. Kinoshita, T.; Miwa, T. Carbohydrate Res., 1973, 28, 175; Kinoshita, T.; Miyano, K.; Miwa, T. Bull. Chem. Soc. Japan, 1975, 48, 1865; Kinoshita, T.; Miwa, T. Bull. Chem. Soc. Japan, 1978, 57, 225; Beddoes, R. L.; Lewis, M. L.; Gilbert, P.; Quayle, P.; Thompson, S. P.; Wang, S.; Mills, K. Tetrahedron Lett., 1996, 37, 9119; Kinoshita, T.; Ichinari, D.; Sinya, J. J. Het. Chem., 1996, 33, 1313.
11. 5. Kinoshita, T.; Miwa, T. Carbohydrate Res., 1973, 28, 175; Kinoshita, T.; Miyano, K.; Miwa, T. Bull. Chem. Soc. Japan, 1975, 48, 1865; Kinoshita, T.; Miwa, T. Bull. Chem. Soc. Japan, 1978, 57, 225; Beddoes, R. L.; Lewis, M. L.; Gilbert, P.; Quayle, P.; Thompson, S. P.; Wang, S.; Mills, K. Tetrahedron Lett., 1996, 37, 9119; Kinoshita, T.; Ichinari, D.; Sinya, J. J. Het. Chem., 1996, 33, 1313.
12. 5. Kinoshita, T.; Miwa, T. Carbohydrate Res., 1973, 28, 175; Kinoshita, T.; Miyano, K.; Miwa, T. Bull. Chem. Soc. Japan, 1975, 48, 1865; Kinoshita, T.; Miwa, T. Bull. Chem. Soc. Japan, 1978, 57, 225; Beddoes, R. L.; Lewis, M. L.; Gilbert, P.; Quayle, P.; Thompson, S. P.; Wang, S.; Mills, K. Tetrahedron Lett., 1996, 37, 9119; Kinoshita, T.; Ichinari, D.; Sinya, J. J. Het. Chem., 1996, 33, 1313.
13. 5. Kinoshita, T.; Miwa, T. Carbohydrate Res., 1973, 28, 175; Kinoshita, T.; Miyano, K.; Miwa, T. Bull. Chem. Soc. Japan, 1975, 48, 1865; Kinoshita, T.; Miwa, T. Bull. Chem. Soc. Japan, 1978, 57, 225; Beddoes, R. L.; Lewis, M. L.; Gilbert, P.; Quayle, P.; Thompson, S. P.; Wang, S.; Mills, K. Tetrahedron Lett., 1996, 37, 9119; Kinoshita, T.; Ichinari, D.; Sinya, J. J. Het. Chem., 1996, 33, 1313.
14. 13C nmr, mass spec, IR and elemental analysis or HRMS).
15. 7. Extended enolates usually display a penchant for reaction at the α-centre rather than the γ-centre: for example see, Fleming, I. Frontier Orbitals and Organic Chemical Reactions; Wiley; New York; 1976; Caine, D. In Comprehensive Organic Synthesis; Ed. Trost, B. M; Fleming, I; Pergamon; New York; 1991, vol 2.
16. 7. Extended enolates usually display a penchant for reaction at the α-centre rather than the γ-centre: for example see, Fleming, I. Frontier Orbitals and Organic Chemical Reactions; Wiley; New York; 1976; Caine, D. In Comprehensive Organic Synthesis; Ed. Trost, B. M; Fleming, I; Pergamon; New York; 1991, vol 2.