Exploring the Reactivity of Dioxacyclic Compounds as a Route to Polysubstituted Decalins and Fused Polycycles

Journal of Organic Chemistry

Volumn 63, Issue 3, 1998, Pages 647-656

  Lautens, Mark ^a   Fillion, Eric ^a  

^a UNIVERSITY OF TORONTO   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000575757     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo971567+     Document Type: Article

References (40)

1. For recent reviews on the ring-opening of oxabicyclic systems, see: (a) Chiu, P.; Lautens, M. Topics in Current Chemistry; Springer-Verlag: Berlin, 1997, Vol. 190, p 1. (b) Woo, S.; Keay, B. Synthesis 1996, 669. (c) Lautens, M. Synlett 1993, 177. (d) For the recent use of dioxacyclic compound in synthesis: Mosimann, H.; Vogel, P.; Pinkerton, A. A.; Kirschbaum, K. J. Org. Chem. 1997, 62, 3002.
2. For recent reviews on the ring-opening of oxabicyclic systems, see: (a) Chiu, P.; Lautens, M. Topics in Current Chemistry; Springer-Verlag: Berlin, 1997, Vol. 190, p 1. (b) Woo, S.; Keay, B. Synthesis 1996, 669. (c) Lautens, M. Synlett 1993, 177. (d) For the recent use of dioxacyclic compound in synthesis: Mosimann, H.; Vogel, P.; Pinkerton, A. A.; Kirschbaum, K. J. Org. Chem. 1997, 62, 3002.
3. For recent reviews on the ring-opening of oxabicyclic systems, see: (a) Chiu, P.; Lautens, M. Topics in Current Chemistry; Springer-Verlag: Berlin, 1997, Vol. 190, p 1. (b) Woo, S.; Keay, B. Synthesis 1996, 669. (c) Lautens, M. Synlett 1993, 177. (d) For the recent use of dioxacyclic compound in synthesis: Mosimann, H.; Vogel, P.; Pinkerton, A. A.; Kirschbaum, K. J. Org. Chem. 1997, 62, 3002.
4. For recent reviews on the ring-opening of oxabicyclic systems, see: (a) Chiu, P.; Lautens, M. Topics in Current Chemistry; Springer-Verlag: Berlin, 1997, Vol. 190, p 1. (b) Woo, S.; Keay, B. Synthesis 1996, 669. (c) Lautens, M. Synlett 1993, 177. (d) For the recent use of dioxacyclic compound in synthesis: Mosimann, H.; Vogel, P.; Pinkerton, A. A.; Kirschbaum, K. J. Org. Chem. 1997, 62, 3002.
5. For a recent review on aromatic heterocycles as intermediates in synthesis, see: Shipman, M. Contemp. Org. Synth. 1995, 2, 1.
6. Lautens, M.; Fillion, E. J. Org. Chem. 1997, 62, 4418.
7. Lautens, M.; Fillion, E. J. Org. Chem. 1996, 61, 7994.
8. (a) For regioselective opening: Lautens, M.; Chiu, P. Tetrahedron Lett. 1993, 34, 773.
9. (b) For intramolecular opening: Lautens, M.; Kumanovic, S. J. Am. Chem. Soc. 1995, 777, 1954.
10. Lautens, M.; Ma, S.; Chiu, P. J. Am. Chem. Soc. 1997, 779, 6478.
11. (a) Lautens, M.; Klute, W. Angew. Chem., Int. Ed. Engl. 1996, 35, 442.
12. (b) Lautens, M.; Aspiotis, R.; Colucci, J. J. Am. Chem. Soc. 1996, 118, 10930.
13. Brown, H. C.; Weissman, P. M. J. Am. Chem. Soc. 1965, 87, 5614.
14. Calvani, F.; Crotti, P.; Gardelli, C.; Pineschi, M. Tetrahedron 1994, 50, 12999.
15. MeLi induces ring-opening of unsubstituted oxabicycles when TMEDA is used as the solvent. However, bridgehead-substituted substrates are inert toward MeLi, see: Lautens, M.; Belter, R. K. Tetrahedron Lett. 1992, 33, 2617.
16. Corey, E. J.; Jones, G. B. J. Org. Chem. 1992, 57, 1028.
17. Lautens, M.; Kumanovic, S.; Meyer, C. Angew. Chem., Int. Ed. Engl. 1996, 35, 1329.
18. We have preliminary evidence that azabicyclo[3.2.1] systems also react with organolithium reagent: Lautens, M.; Goldring, W.; Johnstone, S. Unpublished results.
19. (a) Bordwell, F. G. Acc. Chem. Res 1988, 21, 456.
20. (b) March, J. Advanced Organic Chemistry 4th ed.; Wiley-Interscience, Ed.; John Wiley & Sons: New York, 1992; p 248.
21. The authors have deposited atomic coordinates for this structure with the Cambridge Crystallographic Data Centre. The coordinates can be obtained, on request, from the Director, Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge, CB2 1EZ, UK.
22. Schröder, C.; Wolff, S.; Agosta, W. C. J. Am. Chem. Soc. 1987, 109, 5491.
23. The generality of this reaction is still under investigation: Lautens, M.; Fillion, E. Unpublished results.
24. The reluctance of a trisubstituted double bond toward carbolithiation was previously reported in the literature: Krief, A.; Barbeaux, P. Tetrahedron Lett. 1991, 32, 417.
25. 3.
26. (b) The sense of induction was not determined,
27. (c) For the opening of meso oxabicyclo-[3.2.1] with n-BuLi/(-)-sparteine: Lautens, M.; Gajda, C.; Chiu, P. J. Chem. Soc., Chem. Commun. 1993, 1193.
28. (d) Gajda, C. M. Sc. Thesis, Ring-Opening Reactions of Oxabicyclic Compounds: Asymmetric Induction and Solvent Effects, University of Toronto, 1993.
29. Chiu, P. Ph.D. Thesis, Ring-Opening Reactions of Oxabicyclic Compounds: Unsymmetrical Substrates and Reduction, University of Toronto, 1994.
30. For reported deprotonation/fragmentation of "unactivated" ox- abicyclic compounds: (a) Arjona, O.; Conde, S.; Plumet, J.; Viso, A. Tetrahedron Lett. 1995, 36, 6157. (b) Lautens, M.; Ma, S. Tetrahedron Lett. 1996, 37, 1727.
31. For reported deprotonation/fragmentation of "unactivated" ox- abicyclic compounds: (a) Arjona, O.; Conde, S.; Plumet, J.; Viso, A. Tetrahedron Lett. 1995, 36, 6157. (b) Lautens, M.; Ma, S. Tetrahedron Lett. 1996, 37, 1727.
32. For a review on the synthesis of chiral compounds by bond disconnection, see: Gais, H.-J. In Methods of Organic Chemistry (Houben-Weyl), 1996; Vol. E 21a, Part C, p 589. (d) Ho, T. L. Symmetry. A basis for synthetic design; Wiley-Interscience, Ed.; John Wiley & Sons: New York 1995.
33. For a review on the synthesis of chiral compounds by bond disconnection, see: Gais, H.-J. In Methods of Organic Chemistry (Houben-Weyl), 1996; Vol. E 21a, Part C, p 589. (d) Ho, T. L. Symmetry. A basis for synthetic design; Wiley-Interscience, Ed.; John Wiley & Sons: New York 1995.
34. Majewski, M.; Lazny, R. J. Org. Chem. 1995, 60, 5825.
35. For the synthesis of a symmetrical dioxapentacycle and its enantioselective desymmetrization by enantio selective hydroboration, see: Marchionni, C.; Vogel, P.; Roversi, P. Tetrahedron Lett. 1996, 37, 4149.
36. This reaction has been recently used for the enantioselective desymmetrization of aza- and thiaoxabicyclo[3.2.1] and [3.3.1] systems for the synthesis of azepines, thiepines, and thiocines: Lautens, M.; Pillion, E.; Sampat, M. J. Org. Chem. 1997, 62, 7080.
37. Olofson, R. A.; Martz, J, T.; Senet, J.-P.; Piteau, M.; Malroof, T. J. Org, Chem, 1984, 49, 2081.
38. (a) For an excellent review on enantioselective deprotonation: Beak, P.; Basu, A.; Gallagher, D. J.; Park, Y. S.; Thayumanavan, S. Acc. Chem. Res 1996, 29, 552.
39. (b) For examples of deprotonation - elimination, see: (b) Beak, P.; Lee, W. K. J. Org. Chem. 1993,58,1109.
40. (c) Garrido, F.; Mann, A.; Wermuth, C.-G. Tetrahedron Lett. 1997,38, 63.