Diastereoselective manipulations of bicyclo[m.1.0]alkane derivatives. 5. α'-Alkylations of bicycle[m.1.0]alkan-2-ones

Tetrahedron

Volumn 54, Issue 12, 1998, Pages 2669-2682

  Mash, Eugene A ^a   Baron, James A ^a   Gregg, Timothy M ^a   Nimkar, Sandeep K ^a  

^a University of Arizona   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALKANE DERIVATIVE;

ALKYLATION; ARTICLE; DIASTEREOISOMER; PRIORITY JOURNAL; STEREOSPECIFICITY;

EID: 0032546294     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(98)83003-2     Document Type: Article

References (33)

1. (a) Mash, E. A.; Math, S. K.; Arterburn, J. B. J. Org. Chem. 1989, 54, 4951-4953.
2. (b) Mash, E. A.; Torok, D. S. J. Org. Chem. 1989, 54, 250-253.
3. (c) Mash, E. A.; Nelson, K. A. Tetrahedron 1987, 43, 679-692.
4. see also (d) Yeh, S.-M.; Huang, L.-H.; Luh, T.-Y. J. Org. Chem. 1996, 61, 3906-3908.
5. (a) Mash, E. A.; Gregg, T. M.; Stahl, M. T.; Walters, W. P. J. Org. Chem. 1996, 61, 2738-2742. See also
6. (b) Mash, E. A.; Gregg, T. M.; Stahl, M. T. J. Org. Chem. 1997, 62, 3715-3721.
7. (a) Mash, E. A.; Gregg, T. M.; Kaczynski, M. A. J. Org. Chem. 1996, 61, 2743-2752.
8. (b) Mash, E. A.; Gregg, T. M.; Baron, J. A. J. Org. Chem. 1997, 62, 8513-8521.
9. See also (c) Mash, E. A.; Nimkar, K. S.; Baron, J. A. Tetrahedron 1997, 53, 9043-9056.
10. (a) Nelson, K. A.; Mash, E. A. J. Org. Chem., 1986, 51, 2721-2724.
11. (b) Mash, E. A.; Fiyling, J. A. J. Org. Chem., 1987, 52, 3000-3003.
12. (c) Mash, E. A. J. Org. Chem. 1987, 52, 4142-4143.
13. (d) Mash, E. A.; Math, S. K.; Flann, C. J. Tetrahedron 1989, 45, 4945-4950.
14. (e) Kabat, M. M.; Kiegiel, J.; Cohen, N.; Toth, K.; Wovkulich, P. M.; Uskokovic M. R. J. Org. Chem. 1996, 61, 118-124.
15. (f) Cossy, J.; BouzBouz, S. Tetrahedron Lett. 1996, 37, 5091-5094.
16. For relevant α-alkylations of cyclic ketones, see (a) Eliel, E. L.; Wilen, S. H.; Mander, L. N. Stereochemistry of Organic Compounds; John Wiley & Sons: New York, 1994, pp 898-901 and references cited therein, (b) Still, W. C.; Galynker, I. Tetrahedron 1981, 37, 3981-3996. (c) Schreiber, S. L.; Smith, D. B.; Schulte, G. J. Org. Chem. 1989, 54, 5994-5996. (d) Neeland, E. G.; Sharadendu, A.; Weiler, L. Tetrahedron Lett. 1996, 37, 5069-5072.
17. For relevant α-alkylations of cyclic ketones, see (a) Eliel, E. L.; Wilen, S. H.; Mander, L. N. Stereochemistry of Organic Compounds; John Wiley & Sons: New York, 1994, pp 898-901 and references cited therein, (b) Still, W. C.; Galynker, I. Tetrahedron 1981, 37, 3981-3996. (c) Schreiber, S. L.; Smith, D. B.; Schulte, G. J. Org. Chem. 1989, 54, 5994-5996. (d) Neeland, E. G.; Sharadendu, A.; Weiler, L. Tetrahedron Lett. 1996, 37, 5069-5072.
18. For relevant α-alkylations of cyclic ketones, see (a) Eliel, E. L.; Wilen, S. H.; Mander, L. N. Stereochemistry of Organic Compounds; John Wiley & Sons: New York, 1994, pp 898-901 and references cited therein, (b) Still, W. C.; Galynker, I. Tetrahedron 1981, 37, 3981-3996. (c) Schreiber, S. L.; Smith, D. B.; Schulte, G. J. Org. Chem. 1989, 54, 5994-5996. (d) Neeland, E. G.; Sharadendu, A.; Weiler, L. Tetrahedron Lett. 1996, 37, 5069-5072.
19. For relevant α-alkylations of cyclic ketones, see (a) Eliel, E. L.; Wilen, S. H.; Mander, L. N. Stereochemistry of Organic Compounds; John Wiley & Sons: New York, 1994, pp 898-901 and references cited therein, (b) Still, W. C.; Galynker, I. Tetrahedron 1981, 37, 3981-3996. (c) Schreiber, S. L.; Smith, D. B.; Schulte, G. J. Org. Chem. 1989, 54, 5994-5996. (d) Neeland, E. G.; Sharadendu, A.; Weiler, L. Tetrahedron Lett. 1996, 37, 5069-5072.
20. Several 3-alkylbicyclo[m.1.0]alkan-2-ones have previously been prepared; see (a) Dauben, W. G.; Shaffer, G. W.; Deviny, E. J. J. Am. Chem. Soc. 1970, 92, 6273-6281. (b) Ceccherelli, P.; Curini, M.; Marcotullio, M. C.; Rosati, O. Tetrahedron 1992, 48, 9767-9774.
21. Several 3-alkylbicyclo[m.1.0]alkan-2-ones have previously been prepared; see (a) Dauben, W. G.; Shaffer, G. W.; Deviny, E. J. J. Am. Chem. Soc. 1970, 92, 6273-6281. (b) Ceccherelli, P.; Curini, M.; Marcotullio, M. C.; Rosati, O. Tetrahedron 1992, 48, 9767-9774.
22. For preparations of 2-4, see Dauben, W. G.; Berezin, G. H. J. Am. Chem. Soc. 1967, 89, 3449-3452.
23. Use of 1.3 equivalents of α-bromotoluene gave 7a in 48% yield and 8a in 85% yield from 2 and 3, respectively, after 24 hours at -22 °C.
24. 13C NMR in determining diastereomer ratios, see Hiemstra, H.; Wynberg, H. Tetrahedron Lett. 1977, 18, 2183-2186.
25. 13C NMR were in agreement with diastereomer ratios from GC/MS analyses.
26. Determined for enolates derived from bicyclic ketones by consideration of Dreiding models. The suitability of available molecular mechanics parameters to enolates derived from α,β-cyclopropyl ketones has not been established at this time.
27. It is not presently known if stereocontrol was lost in the formation of the enolate, in the alkylation, or after alkylation by equilibration.
28. From IR, NMR, and MS data, the dimer, which was repeatably obtained, consists of one or more stereoisomers of i. equation presented
29. α′ dihedral angles (also given) suggest that the α′-hydrogen would exhibit low kinetic acidity, especially at low temperatures. equation presented
30. 3 was also noted.
31. 17 found ii (related to 7a) to be more stable than iii (related to Tb) by 11 kJ/mol, 10a to be more stable than 10b by 4 kJ/mol, 14a to be more stable than 14b by 1 kJ/mol, 17a to be more stable than 17b by 2 kJ/mol, and v (related to 19b) to be more stable than iv (related to 19a) by 4 kJ/mol. equation presented
32. (a) BATCHMIN, 4.0; Columbia University: New York, 1993.
33. (b) Mohamadi, F.; Richards, N. G. J.; Guida, W. C.; Liskamp, R.; Lipton, M.; Caufield, C.; Chang, G.; Hendrickson, T.; Still, W. C. J. Comp. Chem. 1990, 11, 440-467.