The stereoselective Birch reduction of pyrroles

Tetrahedron Letters

Volumn 40, Issue 3, 1999, Pages 435-438

  Donohoe, Timothy J ^a   Guyo, Paul M ^a   Helliwell, Madeleine ^a  

^a UNIVERSITY OF MANCHESTER   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

PROLINE DERIVATIVE; PYRROLE DERIVATIVE;

ARTICLE; CHEMICAL MODIFICATION; CHEMICAL REACTION; CHIRALITY; PURIFICATION; STEREOCHEMISTRY;

EID: 0033555698     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)02395-8     Document Type: Article

References (15)

1. For reviews of the Birch reduction see: Rabideau, P. W.; Marcinow, Z. Organic Reactions 1992, 42; 1; Mander, L. N. in Comprehensive Organic Synthesis; Ed. Trost, B. M.; Fleming, I.; Pergamon; New York; 1991, Vol 8.
2. For reviews of the Birch reduction see: Rabideau, P. W.; Marcinow, Z. Organic Reactions 1992, 42; 1; Mander, L. N. in Comprehensive Organic Synthesis; Ed. Trost, B. M.; Fleming, I.; Pergamon; New York; 1991, Vol 8.
3. For a review of the stereoselective reduction of hetreocycles see: Donohoe, T. J.; Garg, R.; Stevenson, C. A. Tetrahedron Asymmetry 1996, 7, 317.
4. Donohoe, T. J.; Guyo, P. M. J. Org. Chem. 1996, 61, 7664.
5. Donohoe, T. J.; Guyo, P. M.; Beddoes, R. L.; Helliwell, M. J. Chem. Soc. Perkin Transactions 1 1998, 667.
6. Donohoe, T. J.; Guyo, P. M.; Harji, R. R.; Cousins, R. P. C. Tetrahedron Lett. 1998, 39, 3075.
7. For a recent example see, Schultz, A. G.; Pettus, L. Tetrahedron Lett. 1997, 38, 5433. For a review see Schultz, A. G. Acc. Chem. Res. 1990, 23, 207.
8. For a recent example see, Schultz, A. G.; Pettus, L. Tetrahedron Lett. 1997, 38, 5433. For a review see Schultz, A. G. Acc. Chem. Res. 1990, 23, 207.
9. Donohoe, T. J.; Helliwell, M.; Stevenson, C. A.; Ladduwahetty, T. Tetrahedron Lett. 1998, 39, 3071.
10. See: Whitesell, J. K. Acc. Chem. Res. 1985, 18, 280; Whitesell, J. K. Chem. Rev. 1992, 92, 953; Ihara, M.; Takahashi, M.; Taniguchi, N.; Yasui, K.; Niitsuma, H.; Fukumoto, K. J. Chem. Soc., Perkin Trans. 1 1991, 525.
11. See: Whitesell, J. K. Acc. Chem. Res. 1985, 18, 280; Whitesell, J. K. Chem. Rev. 1992, 92, 953; Ihara, M.; Takahashi, M.; Taniguchi, N.; Yasui, K.; Niitsuma, H.; Fukumoto, K. J. Chem. Soc., Perkin Trans. 1 1991, 525.
12. See: Whitesell, J. K. Acc. Chem. Res. 1985, 18, 280; Whitesell, J. K. Chem. Rev. 1992, 92, 953; Ihara, M.; Takahashi, M.; Taniguchi, N.; Yasui, K.; Niitsuma, H.; Fukumoto, K. J. Chem. Soc., Perkin Trans. 1 1991, 525.
13. 13C-NMR, mass spec, IR and HRMS or microanalysis).
14. Whitesell, J. K.; Bhattacharaya, A.; Henke, K. J. Chem. Soc., Chem. Commun. 1982, 988. For a convenient preparation of (+)- or (-)- TCC see: Comins, D. L.; Salvador, J. M. Tetrahedron Lett. 1993, 34, 801.
15. Whitesell, J. K.; Bhattacharaya, A.; Henke, K. J. Chem. Soc., Chem. Commun. 1982, 988. For a convenient preparation of (+)- or (-)- TCC see: Comins, D. L.; Salvador, J. M. Tetrahedron Lett. 1993, 34, 801.