Bulletin of the Korean Chemical Society

Korean Chemical Society (대한화학회)
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Synthesis of Perhydroisoquinoline Ring Systems by N-Acyliminium Cyclization$^\sharp$

  • Published : 1988.06.20
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Abstract

The stereochemistry of N-acyliminium cyclizations to form decahydropyrrolo[2,1-a]isoquinolin-3(2H)-ones was studied. Particular attention was paid to the stereocontrol by an acetoxy group present on pyrrolidone ring. Two of the three new chiral centers were formed stereospecifically, and the third was controlled by elimination-hydrogenation sequence.

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References

  1. Tetrahedron v.41 W. N. Speckamp;H. Hiemstra
  2. J. Org. Chem. v.47 D. J. Hart;Y.-M. Tsai
  3. J. Org. Chem. v.48 B. E. Maryanoff;D. F. McComsey;B. A. Duhl-Emswiler
  4. J. Am. Chem. Soc. v.105 D. J. Hart;K.-I. Kanai
  5. Tetrahedron Lett. v.21 B. P. Wijnberg;W. N. Speckamp
  6. J. Org. Chem. v.50 D. J. Hart;T.-K. Yang
  7. J. Org. Chem. v.50 A. R. Chamberlain;J. Y. L. Chung
  8. J. Am. Chem. Soc. v.102 D. J. Hart
  9. Tetrahedron v.34 H. E. Schoemaker;J. Dijkink;W. N. Speckamp
  10. Tetrahedron v.34 J. Dijkink;W. N. Speckamp
  11. Tetrahedron Lett. J. Dijkink;W. N. Speckamp
  12. Tetrahedron v.41 J.-K. Choi;D. J. Hart
  13. J. Am. Chem. Soc. v.105 A. R. Chamberlain;J. Y. L. Chung

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  1. Manganese(III) reactions in N-heterocycle synthesis: The preparation of substituted pyrrolidinones vol.39, pp.24, 1988, https://doi.org/10.1016/s0040-4039(98)00746-1