Lanthanide (III) promoted aldol condensation of enones and aldehydes

Synthetic Communications

Volumn 27, Issue 7, 1997, Pages 1191-1197

  Hong, Bor Cherng ^a   Chin, Sheng Fei ^a  

^a NATIONAL CHUNG CHENG UNIVERSITY   (Taiwan)

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE DERIVATIVE; HYDROXYALDEHYDE;

ARTICLE; DRUG SYNTHESIS; IN VITRO STUDY; INFRARED SPECTROPHOTOMETRY; MASS SPECTROMETRY; NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS;

EID: 0031002033     PISSN: 00397911     EISSN: None     Source Type: Journal    
DOI: 10.1080/00397919708003356     Document Type: Article

References (24)

1. (a) Roos, G.; Haines, R.; Raab, C. Synth. Comm. 1993, 23, 1251.
2. (b) Johnson, C. R.; Adams, J. P.; Braun, M. P.; Senanayake, C. B. W. Tetrahedron Lett. 1992, 33, 919.
3. (c) Hwu, J. R., Hakimelahi, G. H., Chou, C.-T., Tetrahedron Lett. 1992, 33, 6469.
4. (d) Leonard, W. R.; Livinghouse, T. J. Org. Chem. 1985, 50, 730.
5. (a) For a review on kinetic acidities of ketones, see: d'Angelo, J. Tetrahedron, 1976, 32, 2979.
6. (b) For a recent review on the formation and aldol reactions of regio-defined enolates, see: Heathcock, C. H. in Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon Press: London, 1991, Vol 2, 181.
7. (c) Kinetically controlled deprotonation of α,β-unsaturated ketones occurs preferentially at the α′-carbon adjacent to the carbonyl group. However, the kinetically preferred site for both protonation and alkylation is the α-carbon, see: (i) Barluenga, J.; Aznar, F.; Cabal, M.; Valdés, C. Tetrahedron Lett. 1989, 30, 5923. (ii) Brown, C. A. J. Org. Chem. 1974, 39, 3913. (iii) Stork, G.; Kraus, G. A. J. Am. Chem. Soc. 1976, 98, 2351. (iv) Stork, G.; Kraus, G. A.; Garcia, G. A. J. Org. Chem. 1974, 39, 3459. (v) Stork, G.; Danheiser, R. L. J. Org. Chem. 1973, 38, 1775.
8. (c) Kinetically controlled deprotonation of α,β-unsaturated ketones occurs preferentially at the α′-carbon adjacent to the carbonyl group. However, the kinetically preferred site for both protonation and alkylation is the α-carbon, see: (i) Barluenga, J.; Aznar, F.; Cabal, M.; Valdés, C. Tetrahedron Lett. 1989, 30, 5923. (ii) Brown, C. A. J. Org. Chem. 1974, 39, 3913. (iii) Stork, G.; Kraus, G. A. J. Am. Chem. Soc. 1976, 98, 2351. (iv) Stork, G.; Kraus, G. A.; Garcia, G. A. J. Org. Chem. 1974, 39, 3459. (v) Stork, G.; Danheiser, R. L. J. Org. Chem. 1973, 38, 1775.
9. (c) Kinetically controlled deprotonation of α,β-unsaturated ketones occurs preferentially at the α′-carbon adjacent to the carbonyl group. However, the kinetically preferred site for both protonation and alkylation is the α-carbon, see: (i) Barluenga, J.; Aznar, F.; Cabal, M.; Valdés, C. Tetrahedron Lett. 1989, 30, 5923. (ii) Brown, C. A. J. Org. Chem. 1974, 39, 3913. (iii) Stork, G.; Kraus, G. A. J. Am. Chem. Soc. 1976, 98, 2351. (iv) Stork, G.; Kraus, G. A.; Garcia, G. A. J. Org. Chem. 1974, 39, 3459. (v) Stork, G.; Danheiser, R. L. J. Org. Chem. 1973, 38, 1775.
10. (c) Kinetically controlled deprotonation of α,β-unsaturated ketones occurs preferentially at the α′-carbon adjacent to the carbonyl group. However, the kinetically preferred site for both protonation and alkylation is the α-carbon, see: (i) Barluenga, J.; Aznar, F.; Cabal, M.; Valdés, C. Tetrahedron Lett. 1989, 30, 5923. (ii) Brown, C. A. J. Org. Chem. 1974, 39, 3913. (iii) Stork, G.; Kraus, G. A. J. Am. Chem. Soc. 1976, 98, 2351. (iv) Stork, G.; Kraus, G. A.; Garcia, G. A. J. Org. Chem. 1974, 39, 3459. (v) Stork, G.; Danheiser, R. L. J. Org. Chem. 1973, 38, 1775.
11. (c) Kinetically controlled deprotonation of α,β-unsaturated ketones occurs preferentially at the α′-carbon adjacent to the carbonyl group. However, the kinetically preferred site for both protonation and alkylation is the α-carbon, see: (i) Barluenga, J.; Aznar, F.; Cabal, M.; Valdés, C. Tetrahedron Lett. 1989, 30, 5923. (ii) Brown, C. A. J. Org. Chem. 1974, 39, 3913. (iii) Stork, G.; Kraus, G. A. J. Am. Chem. Soc. 1976, 98, 2351. (iv) Stork, G.; Kraus, G. A.; Garcia, G. A. J. Org. Chem. 1974, 39, 3459. (v) Stork, G.; Danheiser, R. L. J. Org. Chem. 1973, 38, 1775.
12. Lewis acid catalyzed alkylations of cross-conjugated silyl dienol ethers provided routes to α′-alkylated ketones. A short synthesis of the sesquiterpene (±)-arturmerone has been accomplished using the cross-conjugated TMS dienol ether of mesityl oxide, see: Paterson, I. Tetrahedron Lett. 1979, 1519.
13. (a) Trost, B. M.; Hanson, P. R. Tetrahedron Lett. 1994, 35, 8119.
14. (b) Matsumoto, K.; Shimagaki, M.; Nakata, T.; Oishi, T. Tetrahedron Lett. 1993, 34, 4935.
15. (c) Feldman, K. S.; Simpson, R. E. Tetrahedron Lett. 1989, 30, 6985.
16. (a) Excess MVK enolate and/or lanthanides did not improve the yield,
17. (b) Trapping of the lithium enolate of MVK by TMSCl at -78°C afforded only 65% yield, see: Jung, M. E.; McCombs, C. A. Tetrahedron Lett. 1976, 2935.
18. (a) Luche, J.-L.; Rodriguez-Hahn, L.; Crabbé, P. J.C.S. Chem. Comm. 1978, 601.
19. (b) Luche, J.-L.; Gemal, A. L. J. Am. Chem. Soc. 1979, 10, 5848.
20. (c) Narayanan, B. A.; Bunnelle, W. H. Tetrahedron Lett. 1987, 28, 6261.
21. (d) Guo, B.-S.; Doubleday, W.; Cohen, T. J. Am. Chem. Soc. 1987, 109, 4710.
22. 13C NMR, IR, MS, and HRMS). Yields refer to spectroscopically and chromatographically purified (>95%) materials.
23. This is true even in the case of aldehydes which give very low yields of 1,2-addition products in the presence of alkyl lithium or Grignard reagents, see: Imamoto, T.; Kusumoto, T.; Yokoyama, M. J.C.S. Chem. Comm. 1982, 1042.
24. 3 via the typical Kobayashi method and the reaction yielded only 25% of the desired aldol adduct. For the typical Kobayashi reaction, see: Kobayashi, S.; Hachiya, I. J. Org. Chem. 1994, 59, 3590.