α-Lithiation of N-(tert-butoxycarbonyl)-N-(p-methoxyphenyl)allylamines mediated by (-)-sparteine: Enantioselective syntheses of either enantiomer of 3-substituted enecarbamates

Journal of the American Chemical Society

Volumn 118, Issue 48, 1996, Pages 12218-12219

  Weisenburger, Gerald A ^a   Beak, Peter ^a  

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

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE DERIVATIVE; AMINE;

ARTICLE; CHIRALITY; DRUG SYNTHESIS; ENANTIOMER; REACTION ANALYSIS; TECHNIQUE;

EID: 0030470857     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja962793o     Document Type: Article

References (27)

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2. Wu, S.; Lee, S.; Beak, P. J. Am. Chem. Soc. 1996, 118, 715.
3. Park, Y. S.; Boys, M. L.; Beak, P. J. Am. Chem. Soc. 1996, 118, 3757.
4. Hoppe, D.; Hintze, F.; Tebben, P.; Paetow, M.; Ahrens, H.; Schwerdtfeger, J.; Sommerfeld, P.; Haller, J.; Guarnieri, W.; Kolczewski, S.; Hense, T.; Hoppe, I. Pure Appl. Chem. 1994, 66, 1479.
5. Zschage, O.; Hoppe, D. Tetrahedron 1992, 48, 5657.
6. Paulsen, H.; Graeve, C.; Hoppe, D. Synthesis 1996, 141.
7. Klein, S.; Marek, I.; Poisson, J. F.; Normant, J. F. J. Am. Chem. Soc. 1995, 117, 8853.
8. Muci, A. R.; Campos, K. R.; Evans, D. A. J. Am. Chem. Soc. 1995, 117, 9075.
9. Tsukazaki, M.; Tinkl, M.; Roglans, A.; Chapell, B. J.; Taylor, N. J.; Snieckus, V. J. Am. Chem. Soc. 1996, 118, 685.
10. 5.6
11. 7
12. 3.
13. Thayumanavan, S.; Lee, S.; Liu, C.; Beak, P. J. Am. Chem. Soc. 1994, 116, 9755.
14. Basu, A.; Beak, P. J. Am. Chem. Soc. 1996, 118, 1575.
15. Carstens, A.; Hoppe, D. Tetrahedron 1994, 50, 6097.
16. Pirkle, W. H.; Pochapsky, T. C.; Mahler, G. S.; Corey, D. E.; Reno, D. S.; Alessi, D. M. J. Org. Chem. 1986, 51, 4991.
17. 14,15,25
18. Zschage, O.; Schwark, J.-R.; Krämer, T.; Hoppe, D. Tetrahedron 1992, 48, 8377.
19. 3SnCl (1 M solution in hexanes) is necessary in order to obtain consistent enantiomeric ratios.
20. The product (R)-8, derived from 12, contains ca. 20% of the E isomer.
21. The a isomer is obtained in 6% yield.
22. Ahlbrecht, H.; Enders, D.; Santowski, L.; Zimmermann, G. Chem. Ber. 1989, 122, 1995.
23. The erosion of er is attributed to the trans isomer (R)-9 present in (S)-9. The isomers can be separated by preparative HPLC but were not in this case to demonstrate that high enantioenrichment is possible without this added step.
24. Kronenthal, D. R.; Han, C. Y.; Taylor, M. K. J. Org. Chem. 1982, 47, 2765.
25. Beak, P.; Basu, A.; Gallagher, D. J.; Park, Y. S.; Thayumanavan, S. Acc. Chem. Res. 1996, 29, 0000.
26. Furthur work is under way to determine the origin of the 61:39 er observed when 5 is metalated followed by addition of (-)-sparteine and allyl bromide.
27. 3