An Improved Method for the One-Carbon Homologation of Ketones with Acidic α-Hydrogens

Synlett

Volumn 1996, Issue 9, 1996, Pages 875-876

  Mink, Daniel ^a   Deslongchamps, Ghislain ^a  

^a UNIVERSITY OF NEW BRUNSWICK   (Canada)

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[No Author keywords available]

Indexed keywords

EID: 0002861646     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1996-5616     Document Type: Article

References (26)

1. For example, see: Baigrie, L. M.; Seiklay, H. R.; Tidwell, T. T., J. Am. Chem. Soc. 1985, 107, 5391. Sreekumar, C.; Darst, K. P.; Still, W. C., J. Org. Chem. 1980, 45, 4260. Traas, P. C.; Boelens, H.; Takken, H. J., Tetrahedron Lett. 1976, 26, 2287. Matteson, D. S.; Moody, R. J.; Jesthi, P. K., J. Am. Chem. Soc. 1975, 97, 5608. Oldenziel, O. H.; van Leusen, A. M., Tetrahedron Lett. 1973, 16, 1357.
2. For example, see: Baigrie, L. M.; Seiklay, H. R.; Tidwell, T. T., J. Am. Chem. Soc. 1985, 107, 5391. Sreekumar, C.; Darst, K. P.; Still, W. C., J. Org. Chem. 1980, 45, 4260. Traas, P. C.; Boelens, H.; Takken, H. J., Tetrahedron Lett. 1976, 26, 2287. Matteson, D. S.; Moody, R. J.; Jesthi, P. K., J. Am. Chem. Soc. 1975, 97, 5608. Oldenziel, O. H.; van Leusen, A. M., Tetrahedron Lett. 1973, 16, 1357.
3. For example, see: Baigrie, L. M.; Seiklay, H. R.; Tidwell, T. T., J. Am. Chem. Soc. 1985, 107, 5391. Sreekumar, C.; Darst, K. P.; Still, W. C., J. Org. Chem. 1980, 45, 4260. Traas, P. C.; Boelens, H.; Takken, H. J., Tetrahedron Lett. 1976, 26, 2287. Matteson, D. S.; Moody, R. J.; Jesthi, P. K., J. Am. Chem. Soc. 1975, 97, 5608. Oldenziel, O. H.; van Leusen, A. M., Tetrahedron Lett. 1973, 16, 1357.
4. For example, see: Baigrie, L. M.; Seiklay, H. R.; Tidwell, T. T., J. Am. Chem. Soc. 1985, 107, 5391. Sreekumar, C.; Darst, K. P.; Still, W. C., J. Org. Chem. 1980, 45, 4260. Traas, P. C.; Boelens, H.; Takken, H. J., Tetrahedron Lett. 1976, 26, 2287. Matteson, D. S.; Moody, R. J.; Jesthi, P. K., J. Am. Chem. Soc. 1975, 97, 5608. Oldenziel, O. H.; van Leusen, A. M., Tetrahedron Lett. 1973, 16, 1357.
5. For example, see: Baigrie, L. M.; Seiklay, H. R.; Tidwell, T. T., J. Am. Chem. Soc. 1985, 107, 5391. Sreekumar, C.; Darst, K. P.; Still, W. C., J. Org. Chem. 1980, 45, 4260. Traas, P. C.; Boelens, H.; Takken, H. J., Tetrahedron Lett. 1976, 26, 2287. Matteson, D. S.; Moody, R. J.; Jesthi, P. K., J. Am. Chem. Soc. 1975, 97, 5608. Oldenziel, O. H.; van Leusen, A. M., Tetrahedron Lett. 1973, 16, 1357.
6. Kolb, M. Synthesis 1990, 171. Carey, F. A.; Neergaard, J. R. J. Org. Chem. 1971, 36, 2731. Corey, E. J.; Seebach, D. Angew. Chem. 1965, 77, 1134; Angew. Chem., Int. Ed. Engl. 1965, 4, 1075. Corey, E. J.; Seebach, D. Angew. Chem. 1965, 77, 1135; Angew. Chem., Int. Ed. Engl. 1965, 4, 1077.
7. Kolb, M. Synthesis 1990, 171. Carey, F. A.; Neergaard, J. R. J. Org. Chem. 1971, 36, 2731. Corey, E. J.; Seebach, D. Angew. Chem. 1965, 77, 1134; Angew. Chem., Int. Ed. Engl. 1965, 4, 1075. Corey, E. J.; Seebach, D. Angew. Chem. 1965, 77, 1135; Angew. Chem., Int. Ed. Engl. 1965, 4, 1077.
8. Kolb, M. Synthesis 1990, 171. Carey, F. A.; Neergaard, J. R. J. Org. Chem. 1971, 36, 2731. Corey, E. J.; Seebach, D. Angew. Chem. 1965, 77, 1134; Angew. Chem., Int. Ed. Engl. 1965, 4, 1075. Corey, E. J.; Seebach, D. Angew. Chem. 1965, 77, 1135; Angew. Chem., Int. Ed. Engl. 1965, 4, 1077.
9. Kolb, M. Synthesis 1990, 171. Carey, F. A.; Neergaard, J. R. J. Org. Chem. 1971, 36, 2731. Corey, E. J.; Seebach, D. Angew. Chem. 1965, 77, 1134; Angew. Chem., Int. Ed. Engl. 1965, 4, 1075. Corey, E. J.; Seebach, D. Angew. Chem. 1965, 77, 1135; Angew. Chem., Int. Ed. Engl. 1965, 4, 1077.
10. Kolb, M. Synthesis 1990, 171. Carey, F. A.; Neergaard, J. R. J. Org. Chem. 1971, 36, 2731. Corey, E. J.; Seebach, D. Angew. Chem. 1965, 77, 1134; Angew. Chem., Int. Ed. Engl. 1965, 4, 1075. Corey, E. J.; Seebach, D. Angew. Chem. 1965, 77, 1135; Angew. Chem., Int. Ed. Engl. 1965, 4, 1077.
11. Kolb, M. Synthesis 1990, 171. Carey, F. A.; Neergaard, J. R. J. Org. Chem. 1971, 36, 2731. Corey, E. J.; Seebach, D. Angew. Chem. 1965, 77, 1134; Angew. Chem., Int. Ed. Engl. 1965, 4, 1075. Corey, E. J.; Seebach, D. Angew. Chem. 1965, 77, 1135; Angew. Chem., Int. Ed. Engl. 1965, 4, 1077.
12. Carey, F. A.; Court, A. S. J. Org. Chem. 1972, 37, 1926. Corey, E. J.; Erickson, B. W. J. Org. Chem. 1971, 36, 3553. El-Wassimy, M. T. M.; Jørgensen, K. A.; Lawesson, S.-O. J. Chem. Soc. Perkin Trans. 1 1983, 2201. Stork, G.; Zhao, K., Tetrahedron Lett. 1989, 30, 287.
13. Carey, F. A.; Court, A. S. J. Org. Chem. 1972, 37, 1926. Corey, E. J.; Erickson, B. W. J. Org. Chem. 1971, 36, 3553. El-Wassimy, M. T. M.; Jørgensen, K. A.; Lawesson, S.-O. J. Chem. Soc. Perkin Trans. 1 1983, 2201. Stork, G.; Zhao, K., Tetrahedron Lett. 1989, 30, 287.
14. Carey, F. A.; Court, A. S. J. Org. Chem. 1972, 37, 1926. Corey, E. J.; Erickson, B. W. J. Org. Chem. 1971, 36, 3553. El-Wassimy, M. T. M.; Jørgensen, K. A.; Lawesson, S.-O. J. Chem. Soc. Perkin Trans. 1 1983, 2201. Stork, G.; Zhao, K., Tetrahedron Lett. 1989, 30, 287.
15. Carey, F. A.; Court, A. S. J. Org. Chem. 1972, 37, 1926. Corey, E. J.; Erickson, B. W. J. Org. Chem. 1971, 36, 3553. El-Wassimy, M. T. M.; Jørgensen, K. A.; Lawesson, S.-O. J. Chem. Soc. Perkin Trans. 1 1983, 2201. Stork, G.; Zhao, K., Tetrahedron Lett. 1989, 30, 287.
16. Corey, E. J.; Beames, D. J. J. Am. Chem. Soc. 1973, 95, 5829. Marshall, J. A.; Belletire, J. L. Tetrahedron Lett. 1971, 13, 871.
17. Corey, E. J.; Beames, D. J. J. Am. Chem. Soc. 1973, 95, 5829. Marshall, J. A.; Belletire, J. L. Tetrahedron Lett. 1971, 13, 871.
18. Moss, W. O.; Jones, A. C.; Wisedale, R.; Mahon, M. F.; Molloy, K. C.; Bradbury, R. H.; Hales, N. J.; Gallagher, T. J. Chem. Soc. Perkin Trans. 1 1992, 2615.
19. Mikolajczyk, M.; Balczewski, P. Tetrahedron 1992, 40, 8697.
20. Mikolajczyk, M.; Grzejszczak, S.; Zatorski, A.; Mlotkowska, B. Tetrahedron Lett. 1976, 31, 2731.
21. Kruse, C. G.; Broekhof, N. L. J. M.; Wijsman, A.; van der Gen, A. Tetrahedron Lett. 1977, 10, 885.
22. Mikolajczyk, M.; Grzejszczak, S.; Zatorski, A.; Mlotkowska, B.; Gross, H; Costisella, B. Tetrahedron 1978, 34, 3081.
23. Mikolajczyk, M.; Graczyk, P. P.; Wieczorek, M. W. J. Org. Chem. 1994, 59, 1672.
24. Still, W. C.; Gennari, C. Tetrahedron Lett. 1983, 24, 4405.
25. -1.
26. 3): δ 9.62, 9.59, 9.55 (d, 2H, J =1.4, 1.6, 1.3 Hz, mixture of 2 aldehyde isomers), 7.25-7.31 (m, 2H), 6.81-6.86 (m, 2H), 4.58, 4.51 (s, 2H, mixture of 2 aldehyde isomers), 3.79 (s, 3H), 3.2-1.8 (m, 10H); IR (KBr): 2920, 1770, 1680, 1450.