Reductive and base-induced cleavage reactions of oxabicyclic compounds

Tetrahedron Letters

Volumn 37, Issue 11, 1996, Pages 1727-1730

  Lautens, Mark ^a   Ma, Shihong ^a  

^a UNIVERSITY OF TORONTO   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

CYCLOALKANE; CYCLOHEPTANE DERIVATIVE; CYCLOHEXANONE DERIVATIVE;

ARTICLE; CHIRALITY; DRUG SYNTHESIS; NONHUMAN; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0029969242     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)00120-7     Document Type: Article

References (35)

1. a) Vogel, P.; Fattori, D.; Gasparini, F.; Le Drian, C. Synlett 1990, 173.
2. b) Ager, D.J.; East, M.B. Tetrahedron 1993, 26, 5683.
3. c) Shipman, M. Contemporary Org. Synth. 1995, 2(1), 1.
4. d) Hoffmann, H.M.R. Angew. Chem. Int. Ed. Engl. 1984, 23, 1.
5. e) Mann, J. Tetrahedron 1986, 42, 4611.
6. f) Noyori, R. Accts. Chem. Res. 1979, 12, 61.
7. For some recent reviews: a) Lautens, M. Synlett 1993, 177.
8. b) Lautens, M. Pure & Appl. Chem. 1992, 64, 1873.
9. c) Vogel, P. Bull. Soc. Chim. Belg. 1990, 99, 395.
10. Arjona, O.; Conde, S.; Plumet, J.; Viso, A. Tetrahedron Lett. 1995, 36, 6157.
11. a) Vieira, E.; Vogel, P. Helv. Chim. Acta. 1983, 66, 1865.
12. b) Warm, A.; Vogel, P. Helv. Chim. Acta. 1987, 70, 690.
13. c) Black, K.A.; Vogel, P. Helv. Chim. Acta. 1984, 67, 1612.
14. Corey, E.J.; Loh, T.-P. Tetrahedron Lett. 1993, 34, 3979.
15. 2BH was synthesized according to Brown, H.C.; Singaram, B. J. Org. Chem. 1984, 49, 945. For the hydroboration of oxabicyclic systems using achiral borane regents, see:
16. a) Brown, H.C.; Vara Prasad, J.V.N. J. Org. Chem. 1985, 50, 3002.
17. b) Rama Rao, A.V.; Yadav, J.S.; Vidyasagar, V. J. Chem. Soc. Chem. Commun. 1985, 55.
18. Following completion of our work, several improvements in asymmetric hydrometallation have been reported. Hayashi described a very efficient route to compounds closely related to 8 in 90-95% ee using a Pd-MOP catalyzed enantioselective hydrosilylation-oxidation sequence, see: Uozumi, Y.; Hayashi, T. Tetrahedron Lett. 1993, 34, 2335. Catalytic asymmetric hydroboration has also been reported, see: Schnyder, A.; Hintermann, L.; Togni, A. Angew. Chem. Int. Ed. Engl. 1995, 34, 931 and references therein.
19. Following completion of our work, several improvements in asymmetric hydrometallation have been reported. Hayashi described a very efficient route to compounds closely related to 8 in 90-95% ee using a Pd-MOP catalyzed enantioselective hydrosilylation-oxidation sequence, see: Uozumi, Y.; Hayashi, T. Tetrahedron Lett. 1993, 34, 2335. Catalytic asymmetric hydroboration has also been reported, see: Schnyder, A.; Hintermann, L.; Togni, A. Angew. Chem. Int. Ed. Engl. 1995, 34, 931 and references therein.
20. Dale, J.A.; Mosher, H.S. J. Am. Chem. Soc. 1973, 95, 512.
21. Corey, E.J.; Mehrotra, M.M. Tetrahedron Lett. 1986, 27, 5173.
22. 2 deprotonate 7-oxabicyclo[2.2.]heptane-2-carboxylates or 7-oxabicyclo[2.2.1]hept-2-yl alkyl ketones and give ring opening products,
23. a) Brion, F. Tetrahedron Lett. 1982, 23, 5299.
24. b) Campbell, M.M.; Kaye, A.D.; Sainsbury, M. Tetrahedron Lett. 1983, 24, 4745.
25. c) Van Royen, L.A.; Mijngheer, R.; De Clercq, P.J. Tetrahedron Lett. 1983, 24, 3145.
26. d) Rajapaksa, D.; Keay, B.A.; Rodrigo, R. Can. J. Chem. 1984, 62, 826.
27. e) Campbell, M.M.; Kaye, A.D.; Sainsbury, M.; Yavarzadeh, R. Tetrahedron Lett. 1984, 25, 1629.
28. 3): δ 6.08 (1H, ddm, J = 11.7, 3.0 Hz), 5.34 (1H, dm, J = 11.7 Hz), 5.21 (1H, s), 5.04 (1H, s), 4.01 (1H, m), 3.57 (1H, ddm, J = 10.4, 4.4 Hz), 3.06 (1H, m), 2.10 (1H, qdd, J = 7.3, 4.4, 3.0 Hz), 1.89 (1H, br s), 1.59 (1H, d, J = 10.4 Hz), 1.18 (3H, d, J = 7.5 Hz), 1.05 (3H, d, J = 7.3 Hz).
29. 3): δ 6.08 (1H, ddm, J = 11.7, 3.0 Hz), 5.34 (1H, dm, J = 11.7 Hz), 5.21 (1H, s), 5.04 (1H, s), 4.01 (1H, m), 3.57 (1H, ddm, J = 10.4, 4.4 Hz), 3.06 (1H, m), 2.10 (1H, qdd, J = 7.3, 4.4, 3.0 Hz), 1.89 (1H, br s), 1.59 (1H, d, J = 10.4 Hz), 1.18 (3H, d, J = 7.5 Hz), 1.05 (3H, d, J = 7.3 Hz).
30. N2 ring openings of oxabicyclic systems using alkyllithiums, see a) Arjona, O.; Fernandez de la Pradilla, R.; Garcia, E.; Martin-Domenech, A.; Plumet, J. Tetrahedron Lett. 1989, 30, 6437.
31. b) Lautens, M.; Abd-El-Aziz, A.S.; Lough, A. J. Org. Chem. 1990, 55, 5305.
32. c) Arjona, O.; Fernandez de la Pradilla, R.; Mallo, A.; Plumet, J.; Viso, A. Tetrahedron Lett. 1990, 31, 1475.
33. a) De Schrijver, J.; De Clercq, P.J. Tetrahedron Lett. 1993, 34, 4369.
34. b) For a related transformation using photolytic cleavage, see: Cossy, J.; Ranaivosata, J.-L.; Bellosta, V.; Ancerewicz, J.; Ferritto, R.; Vogel, P. J. Org. Chem. 1995, 60, and earlier references therein.
35. The reaction is messy, and the only isolated product was the endo oxabicyclic alcohol from the reduction of the carbonyl group.