Stereoselective reductive alkylation of 2,5-disubstituted pyrroles: A role for naphthalene in the partial reduction of heterocycles

Tetrahedron Letters

Volumn 41, Issue 9, 2000, Pages 1327-1330

  Donohoe, Timothy J ^a   Harji, Rakesh R ^a   Cousins, Rick P C ^b  

^a UNIVERSITY OF MANCHESTER   (United Kingdom)

^b GLAXOSMITHKLINE   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

AMMONIA; HETEROCYCLIC COMPOUND; LITHIUM; NAPHTHALENE; PYRROLE DERIVATIVE;

ALKYLATION; ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; CONTROLLED STUDY; REACTION ANALYSIS; REDUCTION; STEREOCHEMISTRY; STRUCTURE ANALYSIS;

EID: 0034716517     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)02314-X     Document Type: Article

References (11)

1. 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, 667; Donohoe, T. J.; Guyo, P. M.; Harji, R. R.; Cousins, R. P. C. Tetrahedron Lett. 1998, 39, 3075.
2. 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, 667; Donohoe, T. J.; Guyo, P. M.; Harji, R. R.; Cousins, R. P. C. Tetrahedron Lett. 1998, 39, 3075.
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, 667; Donohoe, T. J.; Guyo, P. M.; Harji, R. R.; Cousins, R. P. C. Tetrahedron Lett. 1998, 39, 3075.
4. Donohoe,T. J.; Guyo, P. M.; Helliwell, M. Tetrahedron Lett. 1999, 40, 435; Schäfer, A.; Schäfer, B. Tetrahedron 1999, 55, 12309.
5. Donohoe,T. J.; Guyo, P. M.; Helliwell, M. Tetrahedron Lett. 1999, 40, 435; Schäfer, A.; Schäfer, B. Tetrahedron 1999, 55, 12309.
6. Donohoe,T. J.; Helliwell, M.; Stevenson, C. A.; Ladduwahetty, T. Tetrahedron Lett. 1998, 39, 3071.
7. Donohoe,T. J.; Harji, R. R.; Cousins, R. P. Chem. Commun. 1999, 141.
8. Martina, S.; Volker, E.; Wegner, G.; Schluter, A. D. Synthesis 1991, 613.
9. 13C NMR, mass spectra, IR and HRMS or microanalysis).
10. For leading references on the use of lithium naphthalenide in organic synthesis, see: Handbook of Reagents for Organic Synthesis: Oxidising and Reducing Agents; Burke, S. D.; Danheiser, R. L., Eds.; John Wiley: New York, 1999.
11. For a recent example of reductive lithiation using catalytic naphthalene, see: Huerta, F. F.; Gómez, C.; Yus, M. Tetrahedron 1999, 55, 4043.