The effect of the acidifying group on the regioselectivity of the base-induced ring opening of hetero-oxabicyclic [3.2.1] and [3.3.1] systems

Tetrahedron Letters

Volumn 39, Issue 12, 1998, Pages 1501-1504

  Lautens, Mark ^a   Fillion, Eric ^a   Sampat, Michael ^a  

^a UNIVERSITY OF TORONTO   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

BASE; HETEROCYCLIC COMPOUND; OCTANE;

ARTICLE; STRUCTURE ACTIVITY RELATION;

EID: 0032546335     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)00052-5     Document Type: Article

References (16)

1. 1. Roxburgh, C. J. Tetrahedron 1993, 49, 10749.
2. 2. Evans, P. A.; Holmes, A. B. Tetrahedron 1991, 47, 9131.
3. 3. Lautens, M.; Fillion, E.; Sampat, M. J. Org. Chem. 1997, 62, 7080.
4. 4. Klein, L. L.; Shanklin, M. S. J. Org. Chem. 1988, 53, 5202.
5. 5. (a) Cope, A. C.; Anderson, B. C. J. Am. Chem. Soc. 1955, 77, 995.
6. (b) Birch, V. S. F.; Dean, R. A. Liebigs Ann. Chem. 1954, 586, 234.
7. 6. Ram, S.; Spicer, L. D. Tetrahedron Lett. 1987, 28, 515.
8. 7. For an example of a regioselective deprotonation influenced by a β-substituent, see: Corey, E. J.; Chen, R. H. K. Tetrahedron Lett. 1973, 14, 3817.
9. 8. For a review on enantioselective deprotonation, see: Beak, P.; Basu, A.; Gallagher, D. J.; Park, Y. S.; Thayumanavan, S. Acc. Chem. Res. 1996, 29, 552.
10. 9. King, J. F.; Rathore, R. J. Am. Chem. Soc. 1990, 112, 2001.
11. 10. For examples of deprotonation-elimination, see: (a) Beak, P.; Lee, W. K. J. Org. Chem. 1993, 58, 1109.
12. (b) Garrido, F.; Mann, A.; Wermuth, C.-G. Tetrahedron Lett. 1997, 38, 63.
13. 11. Review: Hodgson, D. M.; Gibbs, A. R.; Lee, G. P. Tetrahedron 1996, 52, 14361.
14. 12. Mann, J. Tetrahedron 1986, 42, 4611.
15. 13. With the advent of methods for the enantioselective synthesis of oxabicyclo[3.2.1] substrates, this sequence should be readily adapted to the preparation of enantiomerically pure thiocines, see: (a) Davies, H. M. L.; Ahmed, G.; Churchill, M. R. J. Am. Chem. Soc. 1996, 118, 10774.
16. (b) Lautens, M.; Aspiotis, R.; Colucci, J. J. Am. Chem. Soc. 1996, 118, 10930.