Preparation and utility of cyclic enol carbonates

Synthesis

Volumn , Issue 9, 2004, Pages 1399-1408

  Maddess, Matthew L ^a   Lautens, Mark ^a  

^a UNIVERSITY OF TORONTO   (Canada)

Author keywords

Aldol reactions; Enols; Regioselectivity; Stereoselectivity; Tandem reactions

Indexed keywords

CARBONATES; ETHERS; LOW TEMPERATURE EFFECTS; POTASSIUM; REACTION KINETICS; STEREOCHEMISTRY;

ENOL CARBONATES; MANNICH REACTION; TRANSMETALLATION;

SYNTHESIS (CHEMICAL);

CARBONIC ACID DERIVATIVE; ETHER DERIVATIVE; IODINE DERIVATIVE; POTASSIUM DERIVATIVE;

ALDOL REACTION; ARTICLE; CHEMICAL REACTION; MANNICH REACTION; SILYLATION; STEREOCHEMISTRY; SYNTHESIS; TEMPERATURE;

EID: 3042789076     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2004-822401     Document Type: Article

References (38)

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24. Additional details for the preparation of substrates including isolation and characterization data are available upon request.
25. A procedure employing BuLi was also used extensively.
26. Due to inseparable mixtures and low diastereomeric ratios, full results are not reported at this time although representative procedures are provided.
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28. 3N. Trimethylsilyl and triethylsilyl triflates gave products of low stability.
29. To the best of our knowledge neither vinyl triflates nor silyl enol ethers containing a β-tert-butyl carbonate moiety have previously been prepared. Nor have the parent ketone compounds ever been used directly in an aldol or Michael reaction. This is perhaps a reflection of their base sensitivity.
30. Prepared by modification of a literature protocol: Touleec, P.; Martin, A. C.; Gio-Batta, M.; Bruneau, C.; Dixneuf, P. H. Tetrahedron Lett. 2000, 41, 5527.
31. Prepared by modification of a literature protocol: Iritani, K.; Yanagihara, N.; Utimoto, K. J. Org. Chem. 1986, 51, 5501.
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33. From ketenes, see: (a) Haner, R.; Laube, T.; Seebach, D. J. Am. Chem. Soc. 1985, 107, 5396. (b) Baigrie, L. M.; Lenoir, D.; Seikaly, H. R.; Tidwell, T. T. J. Org. Chem. 1985, 50, 2105. (c) Baigrie, L. M.; Seikaly, H. R.; Tidwell, T. T. J. Am. Chem. Soc. 1985, 107, 5391. (d) O'Neill, P.; Hegarty, A. F. J. Org. Chem. 1987, 52, 2113.
34. From ketenes, see: (a) Haner, R.; Laube, T.; Seebach, D. J. Am. Chem. Soc. 1985, 107, 5396. (b) Baigrie, L. M.; Lenoir, D.; Seikaly, H. R.; Tidwell, T. T. J. Org. Chem. 1985, 50, 2105. (c) Baigrie, L. M.; Seikaly, H. R.; Tidwell, T. T. J. Am. Chem. Soc. 1985, 107, 5391. (d) O'Neill, P.; Hegarty, A. F. J. Org. Chem. 1987, 52, 2113.
35. From ketenes, see: (a) Haner, R.; Laube, T.; Seebach, D. J. Am. Chem. Soc. 1985, 107, 5396. (b) Baigrie, L. M.; Lenoir, D.; Seikaly, H. R.; Tidwell, T. T. J. Org. Chem. 1985, 50, 2105. (c) Baigrie, L. M.; Seikaly, H. R.; Tidwell, T. T. J. Am. Chem. Soc. 1985, 107, 5391. (d) O'Neill, P.; Hegarty, A. F. J. Org. Chem. 1987, 52, 2113.
36. From allylic alkoxides, see: Gazzard, L. J.; Motherwell, W. B.; Sandham, D. A. J. Chem. Soc., Perkin Trans, 1 1999, 8, 979.
37. From esters (cyclic), see: Fehr, C.; Galindo, J. J. Org. Chem. 1988, 53, 1830.
38. For spectral details, see for example: Cardillo, G.; Orena, M.; Porzi, G.; Sandri, S.; Tomasini, C. J. Org. Chem. 1984, 49, 701.