Regiochemical aspects of intramolecular cycloadditions of nitrones derived from N-(2-alkenyl)-2-pyrrolecarbaldehydes. Competitive entries to pyrrolizidine and indolizidine derivatives

  • Broggini G
  • La Rosa C
  • Pilati T
 et al. 
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Abstract

Intramolecular cycloadditions of unsaturated nitrones derived from a series of N-(2-alkenyl)-2-pyrrolecarbaldehydes (2) have been systematically studied. A pronounced substituent effect has been observed as far as the competitive formation of fused- and bridged-ring regioisomers are concerned. Further elaboration of the two kinds of cycloadducts has given pyrrolizidine and indolizidine derivatives, respectively. © 2001 Elsevier Science Ltd. All rights reserved.

Author-supplied keywords

  • Indolizidines
  • Intramolecular cycloaddition
  • Nitrones
  • Pyrrolizidines
  • Regioselection

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