A direct catalytic and diastereoselective aldol route to protected α,β-dihydroxyketones

Synlett

Volumn , Issue 7, 2004, Pages 1195-1198

  Willis, Michael C ^a   Cutting, Gary A ^a   John, Matthew P ^b  

^a University of Bath Claverton Down   (United Kingdom)

^b GLAXOSMITHKLINE   (United Kingdom)

Author keywords

Aldol reactions; Lewis acids; Magnesium; Protecting groups

Indexed keywords

BIPYRIDINE DERIVATIVE; KETONE DERIVATIVE; MAGNESIUM DERIVATIVE; MORPHINE DERIVATIVE;

ARTICLE; CATALYSIS; STEREOCHEMISTRY; SUBSTITUTION REACTION;

EID: 3042624536     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2004-822921     Document Type: Article

References (25)

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4. For recent examples, see: (a) Carda, M.; Falomir, E.; Murga, J.; Castillo, E.; González, F.; Marco, J. A. Tetrahedron Lett. 1999, 40, 6845. (b) Sasaki, S.; Hamada, Y.; Shioiri, T. Tetrahedron Lett. 1999, 40, 3187. (c) Andrus, M. B.; Meredith, E. L.; Sekhar, B. V. S. Org. Lett. 2001, 3, 259. (d) Roush, W. R.; Pfeifer, L. A.; Marron, T. G. J. Org. Chem. 1998, 63, 2064. (e) Crimmins, M. T.; Choy, A. L. J. Am. Chem. Soc. 1999, 121, 5653.
5. For recent examples, see: (a) Carda, M.; Falomir, E.; Murga, J.; Castillo, E.; González, F.; Marco, J. A. Tetrahedron Lett. 1999, 40, 6845. (b) Sasaki, S.; Hamada, Y.; Shioiri, T. Tetrahedron Lett. 1999, 40, 3187. (c) Andrus, M. B.; Meredith, E. L.; Sekhar, B. V. S. Org. Lett. 2001, 3, 259. (d) Roush, W. R.; Pfeifer, L. A.; Marron, T. G. J. Org. Chem. 1998, 63, 2064. (e) Crimmins, M. T.; Choy, A. L. J. Am. Chem. Soc. 1999, 121, 5653.
6. For recent examples, see: (a) Carda, M.; Falomir, E.; Murga, J.; Castillo, E.; González, F.; Marco, J. A. Tetrahedron Lett. 1999, 40, 6845. (b) Sasaki, S.; Hamada, Y.; Shioiri, T. Tetrahedron Lett. 1999, 40, 3187. (c) Andrus, M. B.; Meredith, E. L.; Sekhar, B. V. S. Org. Lett. 2001, 3, 259. (d) Roush, W. R.; Pfeifer, L. A.; Marron, T. G. J. Org. Chem. 1998, 63, 2064. (e) Crimmins, M. T.; Choy, A. L. J. Am. Chem. Soc. 1999, 121, 5653.
7. For recent examples, see: (a) Carda, M.; Falomir, E.; Murga, J.; Castillo, E.; González, F.; Marco, J. A. Tetrahedron Lett. 1999, 40, 6845. (b) Sasaki, S.; Hamada, Y.; Shioiri, T. Tetrahedron Lett. 1999, 40, 3187. (c) Andrus, M. B.; Meredith, E. L.; Sekhar, B. V. S. Org. Lett. 2001, 3, 259. (d) Roush, W. R.; Pfeifer, L. A.; Marron, T. G. J. Org. Chem. 1998, 63, 2064. (e) Crimmins, M. T.; Choy, A. L. J. Am. Chem. Soc. 1999, 121, 5653.
8. For recent examples, see: (a) Carda, M.; Falomir, E.; Murga, J.; Castillo, E.; González, F.; Marco, J. A. Tetrahedron Lett. 1999, 40, 6845. (b) Sasaki, S.; Hamada, Y.; Shioiri, T. Tetrahedron Lett. 1999, 40, 3187. (c) Andrus, M. B.; Meredith, E. L.; Sekhar, B. V. S. Org. Lett. 2001, 3, 259. (d) Roush, W. R.; Pfeifer, L. A.; Marron, T. G. J. Org. Chem. 1998, 63, 2064. (e) Crimmins, M. T.; Choy, A. L. J. Am. Chem. Soc. 1999, 121, 5653.
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11. For examples of direct catalytic aldol reactions using α-oxygenated carbonyls, see: (a) Notz, W.; List, B. J. Am. Chem. Soc. 2000, 122, 7386. (b) Trost, B. M.; Ito, H.; Silcoff, E. R. J. Am. Chem. Soc. 2001, 123, 3367. (c) Yoshikawa, N.; Suzuki, T.; Shibasaki, M. J. Org. Chem. 2002, 67, 2556.
12. For examples of direct catalytic aldol reactions using α-oxygenated carbonyls, see: (a) Notz, W.; List, B. J. Am. Chem. Soc. 2000, 122, 7386. (b) Trost, B. M.; Ito, H.; Silcoff, E. R. J. Am. Chem. Soc. 2001, 123, 3367. (c) Yoshikawa, N.; Suzuki, T.; Shibasaki, M. J. Org. Chem. 2002, 67, 2556.
13. For examples of direct catalytic aldol reactions using α-oxygenated carbonyls, see: (a) Notz, W.; List, B. J. Am. Chem. Soc. 2000, 122, 7386. (b) Trost, B. M.; Ito, H.; Silcoff, E. R. J. Am. Chem. Soc. 2001, 123, 3367. (c) Yoshikawa, N.; Suzuki, T.; Shibasaki, M. J. Org. Chem. 2002, 67, 2556.
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16. For the use of α-carbonate substituted ketones and esters in palladium catalysed cyclopropanation, see: Ogoshi, S.; Morimoto, T.; Nishio, K.; Ohe, K.; Murai, S. J. Org. Chem. 1993, 58, 9.
17. 3 resulted in complex reaction mixtures.
18. Willis, M. C.; Piccio, V. J.-D. Synlett 2002, 1625.
19. For a recent example of a Lewis acid catalysed process in which the addition of an external ligand was needed to achieve reaction, see ref. 5a.
20. 4) and concentrated in vacuo. The crude mixture of dioxolan-2-one diastereomers was purified by flash column chromatography on silica gel (50:1).
21. (4R*,5S*)-4-Benzoyl-5-phenyl-[1,3]dioxolan-2-one is a known compound: Keshava Murthy, K. S.; Dhar, D. N. J. Heterocycl. Chem. 1984, 21, 1721.
22. 3)
23. These observations are based on the isolation of the individual diastereomeric aldol adducts and cyclic carbonates and resubjection of these components to the reaction conditions.
24. For Baeyer-Villiger reactions on similar compounds, see ref. 4c.
25. Baeyer-Villiger oxidation of the phenyl ketone produced an 8:1 mixture of regioisomers, with the desired phenyl ester predominating.