Synthesis of enantiomerically pure anti-aldols: A highly stereoselective ester-derived titanium enolate aldol reaction

Journal of the American Chemical Society

Volumn 118, Issue 10, 1996, Pages 2527-2528

  Ghosh, Arun K ^a   Onishi, Masanobu ^a  

^a UNIVERSITY OF ILLINOIS AT CHICAGO   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

HYDROXYACID;

ARTICLE; DRUG SYNTHESIS; ENANTIOMER; NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS;

EID: 0029879374     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja9539148     Document Type: Article

References (41)

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33. For formation of other titanium enolates from N-propionyloxazolidinones, see: (a) Evans, D. A.; Urpi, F.; Somers, T. C.; Clark, J. S.; Bilodeau, M. T. J. Am. Chem. Soc. 1990, 112, 8215. (b) Evans, D. A.; Rieger, D. L.; Bilodeau, M. T.; Urpi, F. J. Am. Chem. Soc. 1991, 113, 1047. (c) Bonner, M. P.; Thornton, E. R. J. Am. Chem. Soc. 1991, 113, 1299. (d) Siegel, C.; Thornton, E. R. J. Am. Chem. Soc. 1989, 111, 5722. (e) Siegel, C.; Thornton, E. R. Tezrahedron Lett. 1986, 27, 457.
34. For formation of other titanium enolates from N-propionyloxazolidinones, see: (a) Evans, D. A.; Urpi, F.; Somers, T. C.; Clark, J. S.; Bilodeau, M. T. J. Am. Chem. Soc. 1990, 112, 8215. (b) Evans, D. A.; Rieger, D. L.; Bilodeau, M. T.; Urpi, F. J. Am. Chem. Soc. 1991, 113, 1047. (c) Bonner, M. P.; Thornton, E. R. J. Am. Chem. Soc. 1991, 113, 1299. (d) Siegel, C.; Thornton, E. R. J. Am. Chem. Soc. 1989, 111, 5722. (e) Siegel, C.; Thornton, E. R. Tezrahedron Lett. 1986, 27, 457.
35. For formation of other titanium enolates from N-propionyloxazolidinones, see: (a) Evans, D. A.; Urpi, F.; Somers, T. C.; Clark, J. S.; Bilodeau, M. T. J. Am. Chem. Soc. 1990, 112, 8215. (b) Evans, D. A.; Rieger, D. L.; Bilodeau, M. T.; Urpi, F. J. Am. Chem. Soc. 1991, 113, 1047. (c) Bonner, M. P.; Thornton, E. R. J. Am. Chem. Soc. 1991, 113, 1299. (d) Siegel, C.; Thornton, E. R. J. Am. Chem. Soc. 1989, 111, 5722. (e) Siegel, C.; Thornton, E. R. Tezrahedron Lett. 1986, 27, 457.
36. For formation of other titanium enolates from N-propionyloxazolidinones, see: (a) Evans, D. A.; Urpi, F.; Somers, T. C.; Clark, J. S.; Bilodeau, M. T. J. Am. Chem. Soc. 1990, 112, 8215. (b) Evans, D. A.; Rieger, D. L.; Bilodeau, M. T.; Urpi, F. J. Am. Chem. Soc. 1991, 113, 1047. (c) Bonner, M. P.; Thornton, E. R. J. Am. Chem. Soc. 1991, 113, 1299. (d) Siegel, C.; Thornton, E. R. J. Am. Chem. Soc. 1989, 111, 5722. (e) Siegel, C.; Thornton, E. R. Tezrahedron Lett. 1986, 27, 457.
37. 3, 400 MHz): δ 7.78 (d, 2 H, J = 8.3 Hz), 7.16-7.35 (m, 6 H), 5.55 (d, 1 H, J = 5.7 Hz), 4.67 (q, 1 H, J = 7 Hz), 4.28 (m, 1 H), 3.05-3.14 (m, 2 H), 2.50 (s, 3 H), 1.51 (d, 3 H, J = 7.0 Hz).
38. 1H-NMR of crude products revealed the presence of a 65:35 ratio of anti/syn-diastereomers of benzaldehyde and a single anti-isomer of isovaleraldehyde as seen in entry 5.
39. All new compounds gave satisfactory spectroscopic and analytical results.
40. A), 1.72 (dd, 3 H, J = 1.3, 6.5 Hz), 1.66 (m, 1 H, He), 1.47 (s, 3 H), 1.41 (s, 3 H), 0.7 (d, 3 H, J = 6.8 Hz).
41. Zimmerman, H. E.; Traxler, M. D. J. Am. Chem. Soc. 1957, 79, 1920.