Stereospecific dearomatising cyclisation of tertiary α -amidoorganolithiums

Synlett

Volumn , Issue 11, 2003, Pages 1701-1703

  Clayden, Jonathan ^a   Knowles, Faye E ^a   Menet, Christel J ^a  

^a UNIVERSITY OF MANCHESTER   (United Kingdom)

Author keywords

Amide; Cyclisation; Dearomatisation; Lithiation; Stereospecificity

Indexed keywords

ALPHA METHYLBENZYLAMINE; AMIDE; BENZAMIDE DERIVATIVE; CARBON; NITROGEN; ORGANOLITHIUM COMPOUND;

AROMATIZATION; ARTICLE; CHIRALITY; CHROMATOGRAPHY; COVALENT BOND; CYCLIZATION; ENANTIOMER; LITHIATION; NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; STEREOCHEMISTRY; STRUCTURE ANALYSIS; SUBSTITUTION REACTION;

EID: 0041409652     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2003-40993     Document Type: Article

References (27)

1. Basu, A.; Thayumanavan, S. Angew. Chem. Int. Ed. 2002, 41, 716.
2. Carstens, A.; Hoppe, D. Tetrahedron 1994, 50, 6097.
3. For discussions concerning configurational stability and stereospecificity in the reactions of organolithium compounds, see: Clayden, J. Organolithiums: Selectivity for Synthesis; Pergamon: Oxford, 2002.
4. Hammerschmidt, F.; Hanninger, A. Chem. Ber. 1995, 128, 1069.
5. Faibish, N. C.; Park, Y. S.; Lee, S.; Beak, P. J. Am. Chem. Soc. 1997, 119, 11561.
6. Derwing, C.; Frank, H.; Hoppe, D. Eur. J. Org. Chem. 1999, 3519.
7. Hoppe, D.; Kaiser, K.; Stratmann, O.; Fröhlich, R.; Meyer, O.; Hoppe, D. Angew. Chem. Int. Ed. 1997, 36, 2784.
8. Hoppe, D.; Kaiser, B.; Stratmann, O.; Frohlich, R. Angew. Chem. Int. Ed. 1998, 36, 2784.
9. Stratmann, O.; Kaiser, B.; Frohlich, R.; Meyer, O.; Hoppe, D. Chem.-Eur. J. 2001, 7, 423.
10. Gawley, R. E.; Low, E.; Zhang, Q.; Harrris, R. J. Am. Chem. Soc. 2000, 122, 3344.
11. Gawley, R. E. Tetrahedron Lett. 1999, 40, 4297.
12. 20,21 and: Bragg, R. A.; Clayden, J.; Menet, C. J. Tetrahedron Lett. 2002, 43, 1955.
13. (b) The use of a chiral base: Clayden, J.; Menet, C. J.; Mansfield, D. J. Chem. Commun. 2002, 38; or by stereospecific kinetic-isotope-directed lithiation or tinlithium exchange.
14. Ahmed, A.; Clayden, J.; Yasin, S. A. Chem. Commun. 1999, 231.
15. Clayden, J.; Menet, C. J.; Mansfield, D. J. Org. Lett. 2000, 2, 4229.
16. Clayden, J.; Tchabanenko, K.; Yasin, S. A.; Turnbull, M. D. Synlett 2001, 302.
17. For an example of lithiated carbamate unstable towards a stereospecific rearrangement, see: Hara, O.; Ito, M.; Hamada, Y. Tetrahedron Lett. 1998, 39, 5537.
18. 26) allows us confidence in assigning both absolute and relative stereochemistry as shown.
19. The cyclisation can be interpreted as a nucleophilic attack by the organolithium centre on the aromatic ring or as an electrocyclic ring closure, see: Clayden, J.; Purewal, S.; Helliwell, M.; Mantell, S. J. Angew. Chem. Int. Ed. 2002, 41, 1091.
20. Clayden, J.; Menet, C. J. Tetrahedron Lett., in press.
21. Bragg, R. A.; Clayden, J. Tetrahedron Lett. 1999, 40, 8323.
22. Bragg, R. A.; Clayden, J. Tetrahedron Lett. 1999, 40, 8327.
23. Fuji, K.; Kawabata, T. Chem.-Eur. J. 1998, 373.
24. Cuyegkeng, M. A.; Mannschreck, A. Chem. Ber. 1987, 120, 803.
25. Bowles, P.; Clayden, J.; Helliwell, M.; McCarthy, C.; Tomkinson, M.; Westlund, N. J. Chem. Soc., Perkin Trans. 1 1997, 2607.
26. Ahmed, A.; Bragg, R. A.; Clayden, J.; Lai, L. W.; McCarthy, C.; Pink, J. H.; Westlund, N.; Yasin, S. A. Tetrahedron 1998, 54, 13277.
27. Clayden, J.; Knowles, F. E.; Menet, C. J. Tetrahedron Lett. 2003, 44, 3397.