Diastereoselective aldol additions of chiral β-hydroxy ethyl ketone enolates catalyzed by Lewis bases

Organic Letters

Volumn 4, Issue 20, 2002, Pages 3473-3476

  Denmark, Scott E ^a   Fujimori, Shinji ^a  

^a UNIVERSITY OF ILLINOIS AT URBANA CHAMPAIGN   (United States)

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EID: 0041758455     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol026593v     Document Type: Article

References (27)

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2. (b) Cowden, C. J.; Paterson, I. Org. React. 1997, 51, 1.
3. (c) Braun, M. In Stereoselective Synthesis, Methods of Organic Chemistry (Houben-Weyl), Workbench Edition E 21; Helmchen, G., Hoffmann, R. W., Mulzer, J., Schaumann, E., Eds.; Thieme: Stuttgart, 1996; Vol. 3, pp 1644-1655.
4. (a) Denmark, S. E.; Stavenger, R. A. Acc. Chem. Res. 2000, 33, 432.
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7. (a) Denmark, S. E.; Stavenger, R. A.; Winter, S. B. D.; Wong, K.-T.; Barsanti P. A. J. Org. Chem. 1998, 63, 9517. Addition of ester enolates:
8. (b) Denmark, S. E.; Winter, S. B. D.; Su, X.; Wong, K.-T. J. Am. Chem. Soc. 1996, 118, 7404.
9. (c) Denmark, S. E.; Fan, Y. J. Am. Chem. Soc 2002, 124, 4233. Addition of aldehyde enolates:
10. (d) Denmark, S. E.; Ghosh, S. K. Angew. Chem., Int. Ed. 2001, 40, 4059.
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13. Denmark, S. E.; Fujimori, S. Synlett 2001, 1024.
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22. Similar results were obtained for other acyclic ethyl ketone TMS enol ethers in the metal-catalyzed transsilylation process. Denmark, S. E.; Pham, S. M. Unpublished results.
23. (a) Denmark, S. E.; Fu, J. J. Am. Chem. Soc. 2001, 123, 9488.
24. (b) Denmark, S. E.; Wynn, T. J. Am. Chem. Soc. 2001, 123, 6199.
25. In this nomenclature, the first descriptor indicates relative, and the second indicates internal stereochemistry. For discussion of these terms, see: Denmark, S. E.; Almstead, N. G. In Modern Carbonyl Chemistry; Otera, J., Ed.; Wiley-VCH: Weinheim, 2000; Chapter 10.
26. 1H NMR. Denmark, S. E.; Ghosh, S. K.; Wynn, T. A. Unpublished results.
27. A similar transition state analysis was proposed by Paterson for (E)-boron enolate which takes oxygen lone pair repulsions into account. See ref 1b.