Stereospecific Synthesis of trans-1,3-Disubstituted-1,2,3,4-tetrahydro-β-carbolines

Journal of Organic Chemistry

Volumn 46, Issue 1, 1981, Pages 164-168

  Ungemach, F ^a   DiPierro, M ^a   Weber, R ^a   Cook, J M ^a  

^a UNIVERSITY OF WISCONSIN MILWAUKEE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000801022     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo00314a035     Document Type: Article

References (24)

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4. Fox, J. L. Chem. Eng. News 1980, Feb 4th, 24 and work described therein.
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15. Glyoxal diethyl acetal was prepared conveniently by the method of Grohman [Grohman, K.; Noire, P. 172nd National Meeting of the American Chemical Socieity, San Francisco, CA, Aug 30-Sept 3, 1976; abstract no. 236].
16. In the initial series of condensations a 47-mol excess of propionaldehyde was employed. It is believed (NMR, mass spectra) the two byproducts i and ii were produced in this sequence although a rigorous proof of structure has not been completed. The two bases i and ii were not produced when the condensation was run with a slight excess of 2d.
17. Johnson, F. Chem. Rev. 1968, 68, 375.
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19. For a review on the spiroindolenine intermediate, see: Ungemach, F.; Cook, J. M. Heterocycles 1978, 9, 1089.
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23. This sequence parallels the work of Deslongchamps in that attack of the nucleophile on the iminium ion 5a occurs in an antiperiplanar fashion which involves the developing lone pair of electrons on the nitrogen. This is a four-electron process and therefore only anti addition is allowed (Gilchrist, T.; Storr, R. In “Organic Reactions and Orbital Symmetry”, Cambridge University Press: London, 1972). The approach has been employed by Stevens (Stevens, R. V.; Lee, A. W. M. J. Am. Chem. Soc. 1979,101, 7032) and by Wenkert (Wenkert, E.; Chang, C.-J.; Chanta, H. P. S.; Cochran, D. W.; Hagaman, E. W.; King, J. C.; Orito, K. J. Am. Chem. Soc. 1976, 98, 3645) during the stereospecific synthesis of alkaloids.
24. Yamada, S. Y.; Tomioka, K.; Koga, K. Tetrahedron Lett. 1976, 61. Akimoto, H.; Yamada, S., et al. Chem. Pharm. Bull. 1974, 22, 2614.